Vacation 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 July – 7 Aug
4.94 out of 5 average rating, 305 reviews
Guest favourite
Guesthouse 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 Nov
4.9 out of 5 average rating, 202 reviews
Guest favourite
Guesthouse 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 Aug
4.86 out of 5 average rating, 311 reviews

Popular amenities for Annapolis holiday rentals

Stay near Annapolis's top sights

Annapolis City Dock34 locals recommend
Navy-Marine Corps Memorial Stadium34 locals recommend
Graduate Annapolis11 locals recommend
Historic Inns of Annapolis8 locals recommend
Rams Head On Stage22 locals recommend
Boatyard Bar & Grill127 locals recommend

Other great holiday rentals in Annapolis

Guest favourite
Apartment in Crownsville
“River Sweet" Private Apartment
10 – 17 Apr
4.98 out of 5 average rating, 162 reviews
Guest favourite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
29 Aug – 5 Sept
4.94 out of 5 average rating, 349 reviews
Guest favourite
Guest suite in Annapolis
Private 2B Apt--less than 1 mi to Downtown
12 – 19 Nov
4.97 out of 5 average rating, 159 reviews
Guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
8 – 15 Apr
5.0 out of 5 average rating, 103 reviews
Guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
14 – 21 Dec
4.96 out of 5 average rating, 326 reviews
Guest favourite
Apartment in Annapolis
Charming lower-level apartment in Annapolis
14 – 21 June
4.96 out of 5 average rating, 122 reviews
Guest favourite
Guest suite in Annapolis
Cozy Naptown Perch
5 – 12 May
4.96 out of 5 average rating, 162 reviews
Guest favourite
Condo in Annapolis
Funky Uptown Apt meets Downtown - Hist District
23 – 30 Mar
4.96 out of 5 average rating, 50 reviews
Guest favourite
Apartment in Annapolis
Eastport Bungalow
2 – 9 Sept
4.92 out of 5 average rating, 59 reviews
Guest favourite
Guest suite in Arnold
Cozy cottage with riverview and pool
15 – 22 Feb
4.96 out of 5 average rating, 23 reviews
Guest favourite
Guesthouse in Edgewater
1 large room efficiency in detached garage.
14 – 21 July
5.0 out of 5 average rating, 54 reviews
Guest favourite
Apartment in Annapolis
Hillsmere Hideaway
12 – 19 Jan
4.93 out of 5 average rating, 30 reviews

Quick stats about holiday rentals in Annapolis

Total rentals

650 properties

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

Destinations to explore