Holiday rentals in Annapolis
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Top-rated holiday rentals in Annapolis
Guests agree: these stays are highly rated for location, cleanliness, and more.
Guest favourite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
We offer a very tiny, mostly original, cottage built in the 1940’s. Located in the community of Bon Haven, large properties and big trees gives one a cozy, country feel, yet so close to bustling Annapolis! There is RV/EV hookup, an outdoor woodstove, and a propane grill for your use. The yard in the back of the cottage is fully fenced so your dog, cat, or maybe, pig or rabbit 🤔can freely play. Everything is very laid back at Wright’s cottage. Come stay and take the time to enjoy being you!
31 Jul – 7 AugIndividual Host,
€ 187 per night
4.94 out of 5 average rating, 305 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8.
Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace.
Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage!
15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.
10–17 NovIndividual Host,
€ 112 per night
4.9 out of 5 average rating, 202 reviews
Guest favourite
Guest house in Annapolis
Chesapeake Birdhouse Studio
Private, clean, cozy studio in the heart of Eastport, Annapolis. Quiet, separate, retreat space. Walk 1 block to restaurants and bars in Eastport, hop on the water taxi and you are in the heart of Downtown Annapolis, USNA, and historic areas of Annapolis in minutes. This is an Ideal location for the sailing community or anyone visiting our beautiful city. Free street parking available. You could park your car and never have to move it through out your stay. Walk, bike or water taxi.
6–13 AugIndividual Host,
€ 133 per night
4.86 out of 5 average rating, 311 reviews
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Quick stats about holiday rentals in Annapolis
Total rentals | 650 properties |
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Rentals with dedicated workspaces | 340 properties have a dedicated workspace |
Rentals with a pool | 40 properties have a pool |
Pet-friendly rentals | 180 properties allow pets |
Family-friendly rentals | 450 properties are a good fit for families |
Total number of reviews | 28K reviews |
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