Vacation rentals in Annapolis
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Top-rated accommodation in Annapolis
Guests agree: these stays are highly rated for location, cleanliness and more.
Guesthouse in Annapolis
4.9 out of 5 average rating, 202 reviewsCalico 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.
14 – 21 Nov
Guesthouse in Annapolis
4.87 out of 5 average rating, 310 reviewsChesapeake 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.
7 – 14 Aug
Guesthouse in Annapolis
4.97 out of 5 average rating, 152 reviewsLil’ House - A Serene Tiny Home Experience
Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.
21 – 28 July
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Popular amenities for Annapolis accommodation
Other great accommodation in Annapolis
Cottage in Annapolis
4.94 out of 5 average rating, 308 reviewsWright’s Cottage, Pets Welcome!
27 June – 4 July
Guest suite in Arnold
4.94 out of 5 average rating, 110 reviewsCoastal Comfort Suite Near Annapolis, Hottub, EV
3 – 10 Sept
Condo in Annapolis
4.96 out of 5 average rating, 144 reviewsThe Crow's Nest - Excellent downtown Annapolis Apt
24 – 31 Aug
Cottage in Annapolis
4.96 out of 5 average rating, 328 reviewsRelaxing Water Views - Mill Creek Cottage
21 – 28 Dec
Guest suite in Annapolis
4.97 out of 5 average rating, 160 reviewsPrivate 2B Apt--less than 1 mi to Downtown
4 – 11 Nov
Boat in Annapolis
4.94 out of 5 average rating, 349 reviewsStay aboard the S/V MY STUDIO on Annapolis Harbor
6 – 13 Aug
Guest suite in Arnold
4.96 out of 5 average rating, 560 reviewsOld Bay Bungalow
22 – 29 May
Condo in Annapolis
4.96 out of 5 average rating, 51 reviewsFunky Uptown Apt meets Downtown - Hist District
15 – 22 June
Guest suite in Annapolis
4.94 out of 5 average rating, 67 reviewsAnnapolis Garden Suite
26 Apr – 3 May
Guest suite in Riva
5.0 out of 5 average rating, 7 reviewsCozy one bedroom appt on the water
17 – 24 July
Home in Annapolis
4.95 out of 5 average rating, 39 reviewsNaptown Suite
1 – 8 May
Apartment in Annapolis
4.92 out of 5 average rating, 59 reviewsEastport Bungalow
27 Aug – 3 Sept
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 |
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