Annapolis Vacation Rentals

Our Favorite Vacation Rentals in Annapolis

  • Sailing Stray PupPad @ Ego Alley
     Home/Apartment
    Booking.com
    From
    $112
  • Charming and Spacious Annapolis Victorian
    Excellent6br Home/Apartment
    HolidayLettings
    From
    $859
  • 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
  • Luxury Boat & Bed 78' Motor Yacht "Laid Off"
    Excellent4br Boat
    HolidayLettings
    From
    $1,276
  • Annapolis Crows Nest Cottage: Chesapeake Bay View
     5br Country House
    HolidayLettings
    From
    $907
  • 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

  • Bay Getaway
     Home/Apartment
    Airbnb
    From
    $134
  • Boat BNB Luxury Accomadations Aboard a Catamaran
     3br Boat
    Airbnb
    From
    $537
  • Three Miles from Historic Annapolis!
    Excellent5br Home/Apartment
    Airbnb
    From
    $452
  • Annapolis Retreat- 2 mi to DTA/USNA& Private Pool!
    Excellent4br Home/Apartment
    Airbnb
    From
    $1,127

Annapolis Vacation Rentals with Wi-Fi

  • 1B Annapolis Apartment
    GoodHome/Apartment
    Airbnb
    From
    $181
  • Chesapeake Birdhouse Studio
    ExcellentHome/Apartment
    Airbnb
    From
    $170
  • Magnolia Treehouse Guest Suite
    ExcellentHome/Apartment
    Airbnb
    From
    $189
  • Cozy Downtown Annapolis Townhouse
    Excellent3br Home/Apartment
    Airbnb
    From
    $537

Annapolis Pet-Friendly Vacation Rentals

  • Serene Waterfront Apartment on Kent Island
     Home/Apartment
    HolidayLettings
    From
    $238
  • Excellent Location in Downtown Annapolis- walk to everything !
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $547
  • 126-2Dock
     3br Home/Apartment
    HolidayLettings
    From
    $191
  • *BOOK NOW* Beautiful Cottage in historic Annapolis
    Excellent3br Cottage
    HolidayLettings
    From
    $424

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
95 º62
5
88 º40
4
78 º27
7
63 º28
5
61 º6
1
83 º19
6
78 º31
2
86 º37
3
90 º50
7
95 º59
3
96 º65
9
94 º61
8
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Annapolis. The hottest month in Annapolis is June, when temperatures peak at 96 ˚F. The coolest month is December, when temperatures drop to 6 ˚F. The wettest month in Annapolis is June with 8.8 inches of rain, while the driest month is December with 1.36 inches of rain.

What Expert Travelers Think

  • — I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.

    My Anasa
    My AnasaMy Anasa
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School

Vacation Rentals in Annapolis

At AllTheRooms.com we have vacation rentals from all of your favorite providers - Airbnb, Priceline, Bed and Breakfast and more. We have 1,224 vacation rentals, hotels and other places to stay in Annapolis ranging from low-cost options to extravagant places to stay. For those trying to save money, the lowest priced place to stay in Annapolis is only $24 per night. In general, a place to stay in Annapolis will cost you $374 per night.

If you need internet access during your stay in Annapolis, then you can choose from over 759 accommodations that have WiFi internet. 92 of our accommodations come with breakfast in the price. You can keep up with your workout regime by staying at one of 49 accommodations that provide gym facilities. If you are driving to Annapolis, you'll want to pick from 699 places to stay that provide parking. We have 51 vacation rentals that have a pool or jacuzzi.

If you're traveling with your best friend, then make sure to choose one of the 192 pet-friendly accommodations available.

AllTheRooms compares vacation rentals, hotels and other unique accommodation types from loads of providers in Annapolis, including 623 places to stay from Airbnb, 7 accommodations from Priceline and 7 places to stay from Bed and Breakfast

803 of the accommodations in Annapolis have been rated by previous guests. They rated 61% as great. You can instantly book any of 343 places to stay right now.

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