Vacation rentals in Annapolis
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Top-rated vacation rentals 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.
Nov. 14 – 21
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.
Aug. 7 – 14
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.
Jul. 21 – 28
Vacation rentals for every style
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Popular amenities for Annapolis vacation rentals
Other great vacation rentals in Annapolis
Cottage in Annapolis
4.94 out of 5 average rating, 308 reviewsWright’s Cottage, Pets Welcome!
Jun. 27 – Jul. 4
Guest suite in Arnold
4.94 out of 5 average rating, 110 reviewsCoastal Comfort Suite Near Annapolis, Hottub, EV
Sep. 3 – 10
Condo in Annapolis
4.96 out of 5 average rating, 144 reviewsThe Crow's Nest - Excellent downtown Annapolis Apt
Aug. 24 – 31
Cottage in Annapolis
4.96 out of 5 average rating, 328 reviewsRelaxing Water Views - Mill Creek Cottage
Dec. 21 – 28
Guest suite in Annapolis
4.97 out of 5 average rating, 160 reviewsPrivate 2B Apt--less than 1 mi to Downtown
Nov. 4 – 11
Boat in Annapolis
4.94 out of 5 average rating, 349 reviewsStay aboard the S/V MY STUDIO on Annapolis Harbor
Aug. 6 – 13
Guest suite in Arnold
4.96 out of 5 average rating, 560 reviewsOld Bay Bungalow
May 22 – 29
Condo in Annapolis
4.96 out of 5 average rating, 51 reviewsFunky Uptown Apt meets Downtown - Hist District
Jun. 15 – 22
Guest suite in Annapolis
4.94 out of 5 average rating, 67 reviewsAnnapolis Garden Suite
Apr. 26 – May 3
Guest suite in Riva
5.0 out of 5 average rating, 7 reviewsCozy one bedroom appt on the water
Jul. 17 – 24
Home in Annapolis
4.95 out of 5 average rating, 39 reviewsNaptown Suite
May 1 – 8
Apartment in Annapolis
4.92 out of 5 average rating, 59 reviewsEastport Bungalow
Aug. 27 – Sep. 3
Quick stats about vacation 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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