Annapolis Vacation Rentals

Our Favorite Vacation Rentals in Annapolis

  • Sailing Stray PupPad @ Ego Alley
     Home/Apartment
    Booking.com
    From
    $128
  • Charming Home close to historic district
    Excellent2br Home/Apartment
    Flipkey
    From
    $373
  • Walk to Shops/Eateries Charming Cottage. Dogs Wel.
    Excellent3br Cottage
    HolidayLettings
    From
    $816
  • Perfect Annapolis with Lots of Parking & Hot Tub
     4br Home/Apartment
    HolidayLettings
    From
    $610
  • Luxury Boat & Bed 78' Motor Yacht "Laid Off"
    Excellent4br Boat
    HolidayLettings
    From
    $1,276
  • Annapolis House w/ Patio in Bay Ridge Maryland!
     3br Home/Apartment
    HolidayLettings
    From
    $917
  • Charming Annapolis home with stunning water views
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $511
  • Annapolis Crows Nest Cottage: Chesapeake Bay View
     5br Country House
    HolidayLettings
    From
    $592

Check prices for these upcoming dates

Annapolis Vacation Rentals with a Pool

  • Hunter 36' Sailboat
    Excellent2br Home/Apartment
    Airbnb
    From
    $130
  • Martins Cove Hideaway
    ExcellentStudio
    Airbnb
    From
    $158
  • Three Miles from Historic Annapolis!
    Excellent5br Home/Apartment
    Airbnb
    From
    $367
  • Annapolis Retreat- 2 mi to DTA/USNA& Private Pool!
    Excellent4br Home/Apartment
    Airbnb
    From
    $1,031

Annapolis Vacation Rentals with Wi-Fi

  • Our Annapolis Penthouse
    ExcellentHome/Apartment
    Airbnb
    From
    $121
  • Beautiful New Studio Efficiency
    ExcellentHome/Apartment
    Airbnb
    From
    $226
  • Magnolia Treehouse Guest Suite
    ExcellentHome/Apartment
    Airbnb
    From
    $189
  • Newly Renovated Four Bedroom Home in Annapolis
    Excellent4br Home/Apartment
    Airbnb
    From
    $360

Annapolis Pet-Friendly Vacation Rentals

  • Serene Waterfront Apartment on Kent Island
     Home/Apartment
    HolidayLettings
    From
    $220
  • Excellent Location in Downtown Annapolis- walk to everything !
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $547
  • 126-2Dock
     3br Home/Apartment
    HolidayLettings
    From
    $177
  • Downtown Annapolis Home, Walk to Navy Stadium
     3br Townhouse
    HolidayLettings
    From
    $194

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.

Price and Availability in Annapolis

Most expensive
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The cheapest day to stay at a vacation rental in Annapolis tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Annapolis tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Annapolis is in May, while the cheapest month is in December. The most popular time to book a vacation rental in Annapolis is in the high season in September. Annapolis has its low season in January, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Annapolis

Rainy days
68° 12°
3
68° 16°
2
80° 24°
3
85° 37°
2
94° 51°
6
98° 58°
2
101° 70°
4
96° 66°
2
96° 57°
0
94° 44°
4
65° 26°
1
60° 22°
2
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Annapolis. The hottest month in Annapolis is June, when temperatures peak at 101 ˚F. The coolest month is December, when temperatures drop to 12 ˚F. The wettest month in Annapolis is August with 5.97 inches of rain, while the driest month is April with 0.25 inches of rain.

What Expert Travelers Think

  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit
  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

    Whitney Wear
    Whitney WearTravel Better Guide

Vacation Rentals in Annapolis

Find the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, Priceline, Agoda and many more. We have 1,192 vacation rentals, hotels and other accommodation types in Annapolis ranging from budget options to extravagant places to stay. If you are wanting to keep costs down, the lowest priced place to stay in Annapolis comes in at $24 per night. A typical rental in Annapolis costs on average $365 per night.

If you would like to stay connected during your trip, then you can choose from over 619 accommodations in Annapolis that have WiFi. 88 of our accommodations include a breakfast in the price. You can keep up with your workout routine by staying at one of 43 accommodations that provide gym facilities. If you are driving to Annapolis, you'll want to pick from 590 places to stay that provide parking. We have 52 hotels and vacation rentals that have a pool or jacuzzi.

AllTheRooms has 130 pet-friendly places to stay in Annapolis, so if you're traveling with your cat or dog you won't have any trouble.

In Annapolis AllTheRooms currently compares hotels, vacation rentals, hostels from more than 3 providers, including 634 places to stay from Airbnb, 7 accommodations from Priceline and 7 places to stay from Agoda.

813 of our accommodations in Annapolis have been reviewed and rated. 65% are rated great. You can instantly book any of 339 places to stay right now.

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