Top 50 Vacation Rentals Annapolis (Maryland) 2018

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Annapolis Travel Guide

Maryland’s charming state capital is a calling your name for your next vacation.

Things to do in Annapolis

The city sits along the water of the Chesapeake Bay in Eastern Maryland. Wander through the red brick sidewalks of Downtown Annapolis, where you’ll find restaurants offering the catch of the day, charming shops, and hip cafes. Annapolis is the home of the United States Naval Academy, and tours of the grounds and buildings are always a popular activity. Stroll through the beautiful grounds or take a self-guided tour through the Naval History Museum. Check out the Banneker-Douglass Museum, which tells the stories of Benjamin Banneker and Frederick Douglass, two black men and leaders who fought against slavery. The museum is free, full of history, and housed in the historic Mount Moriah African Methodist Episcopal Church. Other top sites in the city include Ego Alley, where you can stroll along the water’s edge on Dock Street, William Paca House and Garden, and the Maryland State House. Part of Annapolis’s charm is the local culture. People in this town tend to be polite, friendly, and very relaxed.

Best Time to Visit Annapolis

The best time to visit Annapolis is in the spring. Boats and rowers line the waterways and the flowers are in full bloom, making the small city even more beautiful.

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Nice
Hilton Garden Inn Annapolis Downtown
120br 3-star Hotel
120 Bedrooms
Gym,
Parking,
Wifi
- Details
Description
Property Location />You'll be centrally located in Annapolis with a stay at O'Callaghan Annapolis Hotel, minutes from Ballet Theater of Maryland and Maryland State House. This hotel is within close proximity of St. John's College and Navy-Marine Corps Memorial Stadium. Rooms />Make yourself at home in one of the 120 air-conditioned rooms featuring refrigerators. Premium TV channels and video-game consoles are provided for your entertainment, while complimentary high-speed (wired) Internet access keeps you connected. Bathrooms have designer toiletries and...
Amenities
Gym
Parking
Wifi
Additional info
Bedrooms:120
Rating Overall Score78%
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Good
The Westin Annapolis
225br 3-star Hotel
225 Bedrooms
Gym,
Parking,
Pets OK,
Pool,
Wifi
- Details
Description
Property Location />With a stay at The Westin Annapolis in Annapolis, you'll be minutes from Ballet Theater of Maryland and close to Maryland State House. This 4-star hotel is within close proximity of Navy-Marine Corps Memorial Stadium and St. John's College. Rooms />Make yourself at home in one of the 223 air-conditioned rooms featuring minibars and flat-screen televisions. Wireless Internet access (surcharge) is available to keep you connected. Private bathrooms with shower/tub combinations feature designer toiletries and hair dryers....
Amenities
Gym
Parking
Pets OK
Pool
Wifi
Additional info
Bedrooms:225
Rating Overall Score85%
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Good
Hotel Annapolis
215br 4-star Hotel
215 Bedrooms
Breakfast,
Gym,
Parking,
Pets OK,
Wifi
Deep Discount
- Details
Description
Property Location />You'll be centrally located in Annapolis with a stay at Loews Annapolis Hotel, minutes from Maryland State House and William Paca House. This 4-star hotel is within close proximity of St. John's College and Ballet Theater of Maryland. Rooms />Make yourself at home in one of the 215 guestrooms featuring refrigerators and flat-screen televisions. Your pillowtop bed comes with Frette Italian sheets. Complimentary wired and wireless Internet access keeps you connected, and satellite programming provides entertainment. Private...
Amenities
Breakfast
Gym
Parking
Pets OK
Wifi
Additional info
Bedrooms:215
Rating Overall Score82%
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Nice
Holiday Inn Express Hotel & Suites Annapolis
79br 3-star Hotel
79 Bedrooms
Breakfast,
Gym,
Parking,
Wifi
- Details
Description
Property Location With a stay at Holiday Inn Express Hotel Suites Annapolis in Annapolis, youll be close to Westfield Annapolis Mall and Maryland State House. This hotel is within close proximity of St. Johns College and Hammond-Harwood House.Rooms Make yourself at home in one of the 79 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless Internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have shower/tub combinations and hair dryers. Conveniences include safes and desks,...
Amenities
Breakfast
Gym
Parking
Wifi
Additional info
Bedrooms:79
Rating Overall Score79%
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Good
Crowne Plaza Annapolis
196br 3-star Hotel
196 Bedrooms
Gym,
Parking,
Pets OK,
Pool,
Wifi,
Smoking
- Details
Description
Property Location />With a stay at Sheraton Annapolis Hotel in Annapolis, you'll be minutes from Westfield Annapolis Mall and close to Maryland State House. This hotel is within close proximity of Navy-Marine Corps Memorial Stadium and Ballet Theater of Maryland. Rooms />Make yourself at home in one of the 196 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless Internet access is available to keep you connected. Bathrooms have complimentary toiletries and hair dryers. Conveniences include phones, as well as...
Amenities
Gym
Parking
Pets OK
Pool
Wifi
Smoking
Additional info
Bedrooms:196
Rating Overall Score81%
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Good
Historic Inns of Annapolis
124br 3-star Hotel
124 Bedrooms
Gym,
Wifi
- Details
Description
A trio of 18th-century homes and lodgings within walking distance of waterfront attractions the non-smoking boutique Historic Inns of Annapolis combine historic charm with the modern comforts that appeal to today's business and leisure guests. Located in the Annapolis Historic District The Maryland Inn Governor Calvert House and Robert Johnson House are relaxing retreats filled with original period details and Victorian reproduction furniture. The Maryland Inn which offers views of the waterfront features 44 rooms as well as a renowned...
Amenities
Gym
Wifi
Additional info
Bedrooms:124
Rating Overall Score81%
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Excellent
Loft over the Heart of Main Street!
1br Home/Apartment
1 Bedroom
1 Bathroom
4 Sleeps
Wifi,
Parking
- Details
Description
Guest Access The entrance to the loft is right behind 164 Main Street. The street address is 15 Francis Street. Its the third floor above a fully functioning restaurant and offices. The loft is completely private. Interaction with Guests We'll be there to greet you, show you how the keys work, and get you settled in. Then we'll leave you alone to enjoy your stay! (We're right nearby to handle anything you need, of course.) The Neighborhood Right in heart of downtown Historic...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:4
Bathrooms:1
Rating Overall Score100%
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Excellent
Cozy private room in Annapolis home
Bedroom
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Pets OK,
Breakfast,
Parking
- Details
Description
The Space Come enjoy a furnished cozy cottage in sought after Historic Annapolis, Maryland. ..the sailing capital of the east coast. Accommodations are simple with open decking and private entrance to bedroom area. A trundle day bed makes into two twins or double bed. A single bath will be shared along with kitchen privileges. The house is situated in a quiet neighborhood with no need for a car. Although parking is easy if you do have a car. A walking path...
Amenities
Wifi
Pets OK
Breakfast
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Good
Charming Eastport Bungalow
Bedroom
1 Bedroom
1 Bathroom
3 Sleeps
Wifi,
Pets OK,
Breakfast,
Parking
- Details
Description
The Space This is not a cookie cutter space, my house was built in 1929 and was renovated 10 years ago. The room has lots of character and is cozy. Many items are treasures I have collected on my travels and I may tell you a story about one or two. Guest Access As mentioned in the description, the bathroom may be shared with other Air B and B guests, as I have another room listed. The shower is a walk-in, meaning no raised...
Amenities
Wifi
Pets OK
Breakfast
Parking
Additional info
Bedrooms:1
Sleeps:3
Bathrooms:1
Rating Overall Score90%
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Excellent
As mentioned in the Washington Post
2br Other
2 Bedrooms
2 Bathrooms
6 Sleeps
Wifi
- Details
Description
The Space As mentioned in the Washington Post: (URL HIDDEN) The space might just be the most convenient space in Downtown Annapolis. You can see both the Capitol and City Dock from the front door. The listing comfortably fits 6 people. The couch serves just like a full bed with back cushions removed. We also provide an air mattress should you need additional beds. There isn't a better back patio in Downtown Annapolis. As of January 20th, 2016, we replaced...
Amenities
Wifi
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:2
Rating Overall Score100%
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Nice
Scotlaur Inn Bed and Breakfast, AnnapolisScotlaur Inn Bed and Breakfast
10br 2.5-star Hotel
10 Bedrooms
Breakfast,
Wifi
- Details
Description
Get an overview of this hotelBayside bed & breakfast with free breakfast and restaurant Location Situated near the bay, this bed & breakfast is within a 10-minute walk of Maryland State House and William Paca House. U.S. Naval Academy is 0.5 mi (0.8 km) away. Property Features A restaurant, a business center, and laundry facilities are available at this bed & breakfast. Free full breakfast and free WiFi in public areas are also provided. Additionally, a library, express check-out, and free newspapers are...
Amenities
Breakfast
Wifi
Additional info
Bedrooms:10
Rating Overall Score76%
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Good
1B Annapolis Apartment
1br Home/Apartment
1 Bedroom
1 Bathroom
4 Sleeps
Wifi,
Parking
- Details
Description
The Space The space is a fully furnished apartment. Guest Access Travelers have complete access to the apartment. Interaction with Guests I am available by phone to offer help throughout your stay. The Neighborhood The apartment is on a quaint neighborhood street in a prime real estate area. ...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:4
Bathrooms:1
Rating Overall Score90%
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Excellent
Steps to the Chesapeake Bay beach
1br Other
1 Bedroom
1 Bathroom
4 Sleeps
Wifi,
Pets OK,
Parking
- Details
Description
The Space PLEASE NOTE: In order to get to the upstairs bedroom, you will need to climb the steep ladder/steps staircase shown in the photos. Guest Access Hot tub Grill Beach Interaction with Guests I strive to give you privacy, yet be available for anything you need. I'm only a call or text away. The Neighborhood Bay Ridge is a slice of heaven. Quiet and secluded, yet 4 miles from downtown and the Naval Academy. A pet friendly neighborhood where people come or walk, run, ride bikes or...
Amenities
Wifi
Pets OK
Parking
Additional info
Bedrooms:1
Sleeps:4
Bathrooms:1
Rating Overall Score100%
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Excellent
Independent Access Garage Apartment, Near Downtown
Bedroom
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Parking
- Details
Description
The Space Our garage apartment is close to downtown Annapolis and several restaurants are available on walking distance. 2 blocks from one of the best breakfasts in Annapolis (Miss Shirley). The room has an independent entrance, comfortable bed, fluffy pillows, and a private bathroom. There is plenty of closet space. Ideal for a weekend getaway! Guest Access Guests have separate entrance to the garage apartment which is located behind our house and street parking is available in front of the house. Interaction with Guests As needed. The...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Good
Peaceful Waterfront Home & Pier 4mi. from downtown
4br Home/Apartment
4 Bedrooms
3 Bathrooms
10 Sleeps
Wifi,
Parking
- Details
Description
The Space Four bedroom waterfront home in Annapolis on 1/2 acre waterfront lot. 4 miles from historic downtown, this home is perfect for a family weekend retreat to discover Annapolis- or to just relax while reading a book on the deck overlooking Oyster Creek. Historic downtown, home to the Naval Academy, countless seafood restaurants, shops, and more, are an easy 8-minute drive away. There are Two bedrooms and baths on the main (second) floor and two bedrooms on the third level...
Amenities
Wifi
Parking
Additional info
Bedrooms:4
Sleeps:10
Bathrooms:3
Rating Overall Score90%
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Excellent
Flag House Inn
2br 4-star Bed & Breakfast
2 Bedrooms
5 Sleeps
- Details
Description
id="propery-desc">The perfect location in downtown Annapolis with free on-site parking, free wi-fi, multiple room configurations, private baths, and in-room cable TV. On the block connecting the historic waterfront and the U.S. Naval Academy in the National Historic District, Flag House Inn offers five guest rooms (including a two-room suite). Enjoy a large, hot breakfast before visiting Flag House’s beautiful and historic neighborhood Splendid interiors are filled with original naval and nautical art and memorabilia, fine paintings, antiques, and reproductions. The...
Additional info
Bedrooms:2
Sleeps:5
Rating Overall Score96%
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Excellent
Charming Downtown Annapolis Studio
1br Studio
1 Bedroom
1 Bathroom
2 Sleeps
Wifi
- Details
Description
The Space This space is a cozy studio tucked away for your privacy but located only 3 blocks from downtown Annapolis and 1 block from the quaint shops on MD Ave. The space is divided into a few areas - a living room with a comfortable satee and a reclining chair, a kitchenette with coffee maker, microwave, small refrigerator, sink, plates, bowls, silverware, glassware and mugs, and a separate bedroom with a queen size bed. There are plenty of...
Amenities
Wifi
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Excellent
Close to Downtown
1br Other
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Parking
- Details
Description
The Space A queen size bed with private bathroom. Guest Access Guest have access to kitchen ...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Good
2A One Bedroom Annapolis Apartment
Bedroom
1 Bedroom
1 Bathroom
4 Sleeps
Wifi,
Parking
- Details
Description
The Space The apartment is on the second floor of a 4 unit apartment building with private entry. Interaction with Guests My guests can call or message me at anytime. ...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:4
Bathrooms:1
Rating Overall Score90%
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Excellent
PRVT Studio Suite w/ Parking- 1 House From Stadium
1br Studio
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Parking
- Details
Description
The Space The space offers a bright, clean, and quiet area to unwind before and after the many events occurring in Annapolis throughout the year. The location is ideal for those attending events at the Navy Marine Corps Stadium as we are across the street from the entrance. We are also a 7-minute walk to the Loews hotel, 10 minutes to Westin/West Street, and 15-20 to downtown. You may choose to ride your bike or uber/lyft downtown for...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Excellent
Sunny room & private bath: walk to downtown
Bedroom
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Breakfast,
Parking
- Details
Description
The Space We have a young German Shepherd training to be a seeing eye dog, and two indoor cats that have access to most of the house (but not the guest bedroom or guest bathroom). We also have hens in the backyard. Guest Access Living room, dining room, porch, fenced in backyard. If you plan on cooking during your stay, please let us know in advance. Interaction with Guests We're usually around, so we can provide recommendations for places to eat and things to do! The Neighborhood Residential...
Amenities
Wifi
Breakfast
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Excellent
GO NAVY! Gorgeous! Next to USNA
4br Other
4 Bedrooms
2 Bathrooms
11 Sleeps
Wifi,
Parking
- Details
Description
The Space We have completely renovated this historic home so it has all of the modern clean lines and coastal decor with the old charm of a historic Annapolis home. Deep rich hardwoods throughout the first floor vastly open living area make it a perfect gathering spot for several couples, a large family of an Navy family hosting many hungry and tired midshipmen. We now have become a hugely popular spot for Downtown Annapolis Weddings...family of the bride at 169 King...
Amenities
Wifi
Parking
Additional info
Bedrooms:4
Sleeps:11
Bathrooms:2
Rating Overall Score100%
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Excellent
Renovated Historic Home Located Downtown -Walk Everywhere!
3br Home/Apartment
3 Bedrooms
2 Bathrooms
7 Sleeps
Pets OK,
Wifi
- Details
Description
We welcome you to our fabulous row house on one of the most coveted areas in all of the Historic District !You will be delighted by this one of a kind home located right in the heart of Downtown Annapolis.We have been a full time vacation rental since 2011 and have loved hosting hundreds of groups Of families and friends coming to visit the city that I'm proud to call my hometown.Im Also proud to be chosen as a...
Amenities
Pets OK
Wifi
Additional info
Bedrooms:3
Sleeps:7
Bathrooms:2
Rating Overall Score97%
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Excellent
Beautiful Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!
3br Other
3 Bedrooms
2 Bathrooms
9 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
Absolutely Charming! Guests will feel right at home in this beautifully renovated 3+ bedroom/2 bath bungalow. Coastal cottage/Pottery Barn decor throughout; expansive gourmet kitchen facing a stunning backyard ideal for outdoor entertaining, crab feasts, morning coffee by the fountain or a glass of wine curled up by the fire pit at night. It's so tranquil its hard to believe you are only steps away from the heart of downtown! Situated only three blocks off West Street in downtown Annapolis, this...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:3
Sleeps:9
Bathrooms:2
Rating Overall Score100%
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Excellent
Romantic Studio on Oyster Creek 4miles-Annapolis
Studio
1 Bathroom
4 Sleeps
Wifi,
Parking
- Details
Description
The Space 2 Kayaks availble to take out on creek and into Chesapeak Bay. Barbeque grill and decks overlooking creek also available. Feel free to bring groceries to prepare in the fully equipped kitchen. Guest Access I have a beautiful backyard overlooking the creek with a Komodo Smoker grill that you are welcome to use. Interaction with Guests I offer a list of restaurants, bars and things to do. If you have any special requests, just let me know in advance and...
Amenities
Wifi
Parking
Additional info
Sleeps:4
Bathrooms:1
Rating Overall Score100%
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Excellent
Bohemian Eastport Bungalow
Bedroom
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Pets OK,
Breakfast,
Parking
- Details
Description
The Space This is a 100 year old, artist's home, full of artwork, oriental rugs and antiques. I have collected many interesting objects during my world travels, which I am sure you will enjoy and there is a story to go with many of my treasures. Guest Access You can relax in back garden, front porch and dining room. As mentioned in the description, the bathroom may be shared with other Air B and B guests, as I have another room listed. The...
Amenities
Wifi
Pets OK
Breakfast
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Excellent
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2br Studio
2 Bedrooms
1 Bathroom
4 Sleeps
Wifi,
Parking
- Details
Description
The Space Although a sailboat; MY STUDIO is basically a two bedroom studio apartment. She has a nicely equipped galley kitchenette, dinning saloon with couches, small desk, a small bathroom (a large head in yachting terms), and two private cabins with storage cabinets. One cabin essentially has a King Size bed, and the other is perfect for smaller crew members with roughly a Full Size bed. If you have really small crew members, we can provide a folding...
Amenities
Wifi
Parking
Additional info
Bedrooms:2
Sleeps:4
Bathrooms:1
Rating Overall Score100%
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Excellent
Wall to Wall Cool
2br Other
2 Bedrooms
1 Bathroom
4 Sleeps
Wifi,
Parking
- Details
Description
The Space This apartment is on one end of a larger main house. The shared wall was retro-fit with sound dampening cellulose fill in February of 2018. This enhancement along with many others provide the feel and comfort of being in your own space. This is Listed as 2 bedrooms, however there is no door between the 2 rooms. They are separated by 3 steps and a hallway. Please see pictures for a thorough view of the layout. Proximity to destinations; Vin...
Amenities
Wifi
Parking
Additional info
Bedrooms:2
Sleeps:4
Bathrooms:1
Rating Overall Score100%
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Excellent
Visiting USNA, stay Downtown. Location, Location!
2br Boat
2 Bedrooms
1 Bathroom
6 Sleeps
Wifi,
Parking
- Details
Description
The Space We couldn't be anymore centrally located in Downtown Annapolis. The house was recently renovated and comfortably holds 6 people. There are 2 bedrooms each with queen beds and a pullout sofa that sleeps 2. The house comes equipped with WI-FI, TV's (cable) in every room, linens and an appropriately stocked kitchen. There's a deck and spacious backyard for those who love to entertain, whether it's for Boat Show, Navy Football or just a get away....
Amenities
Wifi
Parking
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:1
Rating Overall Score100%
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Excellent
LUXURY DOWNTOWN HOME - WALK TO EVERYTHING ANNAPOLIS HAS TO OFFER!
5br Home/Apartment
5 Bedrooms
5 Bathrooms
14 Sleeps
Gym,
Parking,
Wifi
- Details
Description
We are offering our downtown, upscale, renovated house in the extremely desirable location of Murray Hill in Annapolis. This location enables you to walk to everything Annapolis has to offer in ten minutes or less. Come with your car and you never have to move it! We are three blocks from the Westin Hotel complex which offers a fabulous Aveda spa, great pizza pickup, gourmet Italian al fresco dining and always fun Fado Irish...
Amenities
Gym
Parking
Wifi
Additional info
Bedrooms:5
Sleeps:14
Bathrooms:5
Rating Overall Score100%
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Excellent
Just a short drive to downtown Annapolis room 1
Bedroom
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Parking
- Details
Description
The Space Your room features a super-comfy, cushion topped queen bed. Your bathroom and shower are right off the hallway outside of your room. Your bedroom is in the upstairs part of the house. You have an air-cleaner/white noise machine in your room if you choose to use it, but our house and neighborhood are pretty quiet. No television or media upstairs to disturb you: please note that the TV is downstairs in our family room but is available for your...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Excellent
Beautiful New Studio Efficiency
1br Studio
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Parking
- Details
Description
The Space In the heart of colorful Eastport right on Fourth Street, walking distance to everything. Guest Access Private Entrance and private space. Interaction with Guests We are available to help with recommendations for any actives or restaurants you have questions about. The Neighborhood Eastport or the MRE (Maritime Republic of Eastport) is the fun laidback side of Annapolis. Getting Around City bus stop on corner. Uber Water Taxi end of Fourth Street (Seasonal) Pedi Cabs (Seasonal) Other Things to Note Downtown, 0.8 mile 15 minute walk across beautiful Spa Creek,...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Excellent
Comfort & Style: Chesapeake Bay Views, Spa, Kayaks, Pier - 33% Off Sun-Thurs!
6br Country House
6 Bedrooms
3 Bathrooms
22 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
SUMMER SPECIAL! 33% Off Sun - Thurs nights, with 2-night stay. We are very pleased to offer accommodations to Maryland State Delegates serving in the Maryland General Assembly from January through April each year. Enjoy comfort & style steps from the Chesapeake Bay. Rejuvenate, relax and enjoy. Upgraded September 2016! Check out the new Game Room. Main Cottage sleeps 10 Adults in 5 comfy beds; 8 kids in bunk beds; 22 total...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:6
Sleeps:22
Bathrooms:3
Rating Overall Score93%
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Excellent
Historic Downtown Property
3br Other
3 Bedrooms
3 Bathrooms
6 Sleeps
Wifi
- Details
Description
Beautiful historic home right in the heart of downtown Annapolis. Walkable to USNA and all downtown shops and restaurants. This location cannot be beat! 3 Bedroom, 2.5 bath, quiet outdoor patio, gas grill, and charming kitchen....
Amenities
Wifi
Additional info
Bedrooms:3
Sleeps:6
Bathrooms:3
Rating Overall Score100%
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Excellent
Charming historic home just steps from Main Street!
3br Home/Apartment
3 Bedrooms
3 Bathrooms
8 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
Welcome to the heart of historic Annapolis! This charming home (City of Annaplis Rental License #141378) is just steps from Main Street, a block from the City Dock and a 5-minute walk to the visitors’ entrance to the Naval Academy. Originally built in 1830 and lovingly renovated in 2012, the home will provide comfort and convenience for your stay in Maryland’s capital. Whether you are in town for Naval Academy or St. John’s events, a wedding,...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:3
Sleeps:8
Bathrooms:3
Rating Overall Score100%
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Excellent
Annapolis Getaway in Historic District
2br Other
2 Bedrooms
3 Bathrooms
4 Sleeps
Wifi,
Parking
- Details
Description
The Space Two main levels, front porch with Adirondack Chairs, Living Room and Dining Room separated by two-sided fireplace, kitchen and Powder Room on first floor as well as beautiful patio with high-end outdoor furniture. Second Floor Guest Level includes Master Bedroom with attached private bath and Sitting Room which can also be used as a second bedroom with comfortable queen-size sleeper sofa and cable TV. Owner sleeps on top level, but will need access to Hall Bath. Guest Access Guests are welcome...
Amenities
Wifi
Parking
Additional info
Bedrooms:2
Sleeps:4
Bathrooms:3
Rating Overall Score100%
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Good
1A Annapolis Apartment
1br Home/Apartment
1 Bedroom
1 Bathroom
4 Sleeps
Wifi,
Parking
- Details
Description
The Space The apartment is on the lower level with one step into the apartment. There is basic cookware, flat ware, and dishes to allow for cooking meals. Parking is available. Guest Access Guest have full access to the apartment and patio. ...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:4
Bathrooms:1
Rating Overall Score90%
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Good
2B One Bedroom Annapolis Apartment
Bedroom
1 Bedroom
1 Bathroom
4 Sleeps
Wifi
- Details
Description
The Space The apartment is one of 4 units in a two-story apartment building. The unit is located on the second floor in the rear. The entry is private. Guest Access Guest have access to the entire apartment. Interaction with Guests I am available by text or phone. The Neighborhood The Eastport neighborhood is a destination for Annapolitans and locals alike. Located right next to historic downtown Annapolis, youll get a glimpse of what it’s like to live in our quaint colonial town. The apartment is...
Amenities
Wifi
Additional info
Bedrooms:1
Sleeps:4
Bathrooms:1
Rating Overall Score90%
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Excellent
Annapolis Condominium in the Heart of Historic Downtown
3br Home/Apartment
3 Bedrooms
2 Bathrooms
6 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
Unique two floor condominium in Historic Annapolis downtown with 3 bedrooms (one queen, two rooms with two singles per room), living room with 42' flatscreen tv, stereo, kitchen with stainless appliances and granite countertops, and two full bathrooms. All new Beautyrest mattresses in Nov. 2015. Hardwood floors throughout. There is a large deck with city views of the historic Maryland State House. The condo is one half block from Main Street, where coffee bars, restaurants, shops, entertainment and...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:3
Sleeps:6
Bathrooms:2
Rating Overall Score95%
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Excellent
Antique Room Near Annapolis
Bedroom
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Parking
- Details
Description
The Space The home is comfortable with antique, wood floors and articles from my international travels. I have a beautiful brick patio covered with a trellis and a small fountain. It is a perfect place for breakfast or a drink at the end of the day. No outside visitors/guests beyond the number on the reservation. Guest Access The guest has access to the home and kitchen, as well as the backyard. Interaction with Guests I enjoy spending time with the guests and giving them ideas...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Excellent
Gorgeous Southern Colonial on the Water in Annapolis-
6br Other
6 Bedrooms
6 Bathrooms
14 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
2021- Commissioning Week currently available The Yellow House is a charming Southern Colonial, with 6 bedrooms and 5 full baths, and can also be found at (Annapolis waterfront vacationsdotcom). With a large welcoming front porch and multiple decks off the back, and is situated on one of the most picturesque and serene creeks on the bay. A few minutes/5 miles from the center of Historic Annapolis. Its perfect for...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:6
Sleeps:14
Bathrooms:6
Rating Overall Score100%
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Excellent
Charming historic 89 East Street~
3br Other
3 Bedrooms
3 Bathrooms
10 Sleeps
Wifi,
Parking
- Details
Description
The Space The charm of 89 East is that is is a beautiful historic home built in 1875, but has all of the modern conveniences of home. The newly renovated gourmet kitchen with granite countertops provides everything that you need to entertain. We now have a KUERIG along with a regular coffee pot, you choose. The large dining room table seats 8 and the mahogany bar is the perfect spot to gather. There is exposed brick throughout the first floor...
Amenities
Wifi
Parking
Additional info
Bedrooms:3
Sleeps:10
Bathrooms:3
Rating Overall Score100%
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Excellent
Our Annapolis Penthouse
1br Home/Apartment
1 Bedroom
1 Bathroom
3 Sleeps
Wifi,
Parking
- Details
Description
The Space Our studio unit has cathedral ceilings and windows run the length of the unit. This creates a very sunny, spacious feel. Guest Access This studio unit has a private access through the garage. Interaction with Guests I have lived in Annapolis for 40 years and can give suggestions about restaurants, events, transportation and special attractions. We also have printed information available. The Neighborhood Murray Hill is the nicest neighborhood in Annapolis. It is featured on tram tours through Annapolis. Most homes are roughly 100...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:3
Bathrooms:1
Rating Overall Score100%
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Good
Peaceful & clean room(s). Walk to all!
3br Bedroom
3 Bedrooms
3 Bathrooms
7 Sleeps
Wifi,
Parking
- Details
Description
The Space "Chez Joie!" You can walk to most things, it's safe and easy. Historic downtown Annapolis is 1 mile away. Awesome food, shops, bars, spas, private beach, nature trails are all just blocks away. Plenty of free parking. Easy driving access to DC and Baltimore as we are right off rt 50 via Rowe Blvd. Plus, private neighborhood beach access. See Bedroom details listed in photo captions. Guest Access Please use front door and head upstairs. You have access to your room(s)...
Amenities
Wifi
Parking
Additional info
Bedrooms:3
Sleeps:7
Bathrooms:3
Rating Overall Score90%
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Good
Annapolis large peaceful waterfront apartment
2br Home/Apartment
2 Bedrooms
1 Bathroom
4 Sleeps
Wifi,
Parking
- Details
Description
The Space Beautiful peaceful location, bright with natural daylight and gorgeous views of the creek and occasional passing boats. herons and birds. A nice home from home for a quick trip, perhaps a business trip or even a holiday with the family. Although owners live in upper area of house, your apartment is completely private with own entrance and outdoor on the water space, with barbeque. Located Minutes from Historic Annapolis and Rt. 50 giving quick access to both Baltimore and Washington DC. Guest...
Amenities
Wifi
Parking
Additional info
Bedrooms:2
Sleeps:4
Bathrooms:1
Rating Overall Score90%
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Excellent
Hunter 36' Sailboat
2br Boat
2 Bedrooms
1 Bathroom
6 Sleeps
Wifi,
Parking,
Pool
- Details
Description
The Space 36 foot sailboat docked in Annapolis. Boat has heat and air conditioning, high speed wifi, high-def cable TV, microwave, refrigerator, head (toilet), adjacent bath house and cafe. Like a waterfront condo docked at a full-service marina. Great view of boat traffic on Back Creek. Water taxi into downtown Annapolis, several nearby restaurants (including on-premises cafe for breakfast and lunch). I am accessible by cell phone, text or email, and can be at the boat within...
Amenities
Wifi
Parking
Pool
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:1
Rating Overall Score100%
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Excellent
Lovely Private Master Bedroom
Bedroom
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Pets OK,
Parking
- Details
Description
The Space This is a lovely, quiet master bedroom for 1 or 2 with a kitchenette that has a fridge, microwave, and Kuerig coffee maker. Coffee and condiments, plus breakfast snacks are provided. There is a private deck off the room with a table, umbrella, and seating for 4 overlooking the headwaters of Spa Creek. Guest Access Access if through the main house entrance with a key-less entry system, up the stairs and to the left. Interaction with Guests When I am there...
Amenities
Wifi
Pets OK
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Excellent
English Apartment close to Downtown
2br Home/Apartment
2 Bedrooms
1 Bathroom
5 Sleeps
Wifi,
Parking
- Details
Description
The Neighborhood We are in West ANNAPOLIS close to the stadium ...
Amenities
Wifi
Parking
Additional info
Bedrooms:2
Sleeps:5
Bathrooms:1
Rating Overall Score100%
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Excellent
Relaxing Retreat, Walkable to Downtown & Stadium
Retreat
1 Bathroom
4 Sleeps
Wifi,
Parking
- Details
Description
The Space A small kitchenette includes a mini-fridge, a microwave, a toaster oven, and a Keurig. A tv is provided with access to Amazon, Hulu, and Netflix. Guest Access The entrance to the guest space is through a door directly off the patio. Once inside, there are four steps down to the studio apartment in the lower level of the home. Guests have access to the entire space, which includes the kitchenette, bathroom, and laundry room. On occasion, host...
Amenities
Wifi
Parking
Additional info
Sleeps:4
Bathrooms:1
Rating Overall Score100%
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Excellent
Stunning home in the Historic District
4br Home/Apartment
4 Bedrooms
4 Bathrooms
9 Sleeps
Parking,
Wifi
- Details
Description
Thinking about staying in Annapolis with a large group but want an updated Historical house ? Look no further than this property on upper Charles Street in the heart of the Historic District. Our beautiful home is just two blocks from the water and one block from some of the finest restaurants in Maryland. All of the downtown attractions are a five minute walk away- The Market House, Main Street, The Naval Academy , St Marys and the surrounding churches...
Amenities
Parking
Wifi
Additional info
Bedrooms:4
Sleeps:9
Bathrooms:4
Rating Overall Score99%

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Vacation Rentals in Annapolis

Choose the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, VRBO, Homeaway and more. Annapolis has 1045 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. For those trying to keep costs down, the lowest priced place to stay in Annapolis comes in at $12 per night. On average, a place to stay in Annapolis will cost you $375 per night.

If you need an internet connection during your stay in Annapolis, then you can choose from over 701 places to stay that provide WiFi internet. 94 places to stay include a breakfast. Fitness addicts can get a workout in during their stay by choosing from 48 accommodations that have gym facilities. If you are driving to Annapolis, you'll want to pick from 647 places to stay that provide parking. 48 hotels and vacation rentals have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in one of 196 accommodations that are designated as pet-friendly.

We combine a wide variety of Annapolis accommodations including vacation rentals, homestays, hostels and other unique places to stay into one easy search. We show results from more than 6 providers, including 535 places to stay from Airbnb, 151 accommodations from VRBO and 136 places to stay from Homeaway.

653 of our places to stay in Annapolis have been rated by previous guests. They rated 54% as excellent or good. 280 accommodations allow instant booking.

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