Annapolis Vacation Rentals

Our Favorite Vacation Rentals in Annapolis

  • Bayhead
     Country House
    Booking.com
    From
    $700
  • Walk to Shops/Eateries Charming Cottage. Dogs Wel.
    Excellent3br Cottage
    HolidayLettings
    From
    $816
  • Beautiful Murray Hill Home (Annapolis)
    Good4br Home/Apartment
    HolidayLettings
    From
    $561
  • Perfect Annapolis with Lots of Parking & Hot Tub
     4br Home/Apartment
    HolidayLettings
    From
    $610
  • Stunning Home in the Heart of Downtown Annapolis
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $839
  • Luxury Boat & Bed 78' Motor Yacht "Laid Off"
    Excellent4br Boat
    HolidayLettings
    From
    $1,276
  • 2. Private 20 acre waterfront estate - studio apt
     Home/Apartment
    HolidayLettings
    From
    $401
  • Clean & Spacious
     4br Home/Apartment
    HolidayLettings
    From
    $514

Check prices for these upcoming dates

Annapolis Vacation Rentals with a Pool

  • Hunter 36' Sailboat
    Excellent2br Home/Apartment
    Airbnb
    From
    $209
  • Annapolis Waterfront Dream
    Excellent4br Home/Apartment
    Airbnb
    From
    $932
  • 1B Annapolis Condo- Steps from Water and Downtown
     Home/Apartment
    Airbnb
    From
    $198
  • Three Miles from Historic Annapolis!
    Excellent5br Home/Apartment
    Airbnb
    From
    $480

Annapolis Vacation Rentals with Wi-Fi

  • Charming Row House in Historic District
    Excellent2br Boat
    Airbnb
    From
    $302
  • Beautiful New Studio Efficiency
    ExcellentHome/Apartment
    Airbnb
    From
    $226
  • Magnolia Treehouse Guest Suite
    ExcellentHome/Apartment
    Airbnb
    From
    $189
  • Downtown Annapolis Home
    Excellent3br Home/Apartment
    Airbnb
    From
    $565

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
  • *BOOK NOW* Beautiful Cottage in historic Annapolis
    Excellent3br Cottage
    HolidayLettings
    From
    $424
  • 3 BR 2BH House close to navy stadium, and downtown
    Excellent3br Home/Apartment
    Airbnb
    From
    $638

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
78° 27°
7
63° 28°
5
61°
1
61°
1
78° 31°
2
86° 37°
3
90° 50°
7
95° 59°
3
96° 65°
9
61°
1
61°
1
88° 40°
4
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Annapolis. The warmest months in Annapolis are June and July, when temperatures reach 96 ˚F. The coolest month is April, when temperatures drop to 6 ˚F. The wettest month in Annapolis is June with 8.8 inches of rain, while the driest month is April with 1.36 inches of rain.

What Expert Travelers Think

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    Kacie MorganThe Rare Welsh Bit
  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!

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    MonicaNYCTechMommy
  • — 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

Browse vacation rentals from all the leading providers including Airbnb, Priceline, Bed and Breakfast and others at AllTheRooms.com. We have 1,297 vacation rentals, hotels and other accommodation types in Annapolis ranging from budget options to luxury places to stay. When traveling on a budget, the cheapest place to stay in Annapolis is available at $23 per night. An average rental in Annapolis costs on average $370 a night.

If you have to have an internet connection during your time in Annapolis, then you can choose from over 666 accommodations that have WiFi internet. 96 of our accommodations include a breakfast in the price. You can maintain your workout regime by staying at one of 46 accommodations that provide gym facilities. If you're planning on arriving in Annapolis by car, be sure to choose from 628 accommodations that provide parking. We track 53 vacation rentals that have a pool or jacuzzi.

AllTheRooms has 147 pet-friendly places to stay in Annapolis, so if you're traveling with your cat or dog you won't have any problems.

We combine a wide variety of Annapolis accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 4 providers, including 672 places to stay from Airbnb, 7 accommodations from Priceline and 7 places to stay from Bed and Breakfast.

856 of our rentals in Annapolis have been reviewed by previous guests. They rated 64% as excellent or good. You can instantly book any of 360 places to stay right now.

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