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.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Annapolis holiday rentals
Other great holiday rentals in Annapolis
Guest favourite
Cottage in Annapolis
4.94 out of 5 average rating, 312 reviewsWrightβs Cottage, Pets Welcome!
11β18 Jul
Β£200 per night
Guest favourite
Guest suite in Arnold
4.85 out of 5 average rating, 497 reviewsSunny Spot Suite, Serene, Annapolis, Naval Academy
26 Jun β 3 Jul
Β£107 per night
Guest favourite
Boat in Annapolis
4.94 out of 5 average rating, 351 reviewsStay aboard the S/V MY STUDIO on Annapolis Harbor
6β13 Dec
Β£188 per night
Guest favourite
Guest suite in Arnold
4.96 out of 5 average rating, 563 reviewsOld Bay Bungalow
22β29 May
Β£168 per night
Guest favourite
Guest suite in Annapolis
4.97 out of 5 average rating, 162 reviewsPrivate 2B Apt--less than 1 mi to Downtown
1β8 Dec
Β£146 per night
Guest favourite
Flat in Annapolis
4.92 out of 5 average rating, 64 reviewsEastport Bungalow
20β27 Jul
Β£129 per night
Guest favourite
Apartment in Annapolis
4.96 out of 5 average rating, 53 reviewsFunky Uptown Apt meets Downtown - Hist District
11β18 Jun
Β£148 per night
Guest favourite
Guest suite in Arnold
4.96 out of 5 average rating, 24 reviewsCozy cottage with riverview and pool
30 Mar β 6 Apr
Β£129 per night
Quick stats about holiday rentals in Annapolis
Total rentals
640 properties
Rentals with dedicated workspaces
350 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
180 properties allow pets
Family-friendly rentals
440 properties are a good fit for families
Total number of reviews
28K reviews
Destinations to explore
- BaltimoreΒ Holiday rentals
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- Apartment rentalsΒ Annapolis
- Rentals with a fireplaceΒ Annapolis
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- Monthly RentalsΒ Annapolis
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- Rentals with poolsΒ Annapolis
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- Rentals with a hot tubΒ Annapolis
- Pet-friendly rentalsΒ Annapolis
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- Fitness-friendly rentalsΒ Annapolis
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- Family-friendly rentalsΒ Annapolis
- Rentals with breakfastΒ Annapolis
- Rentals with a firepitΒ Annapolis
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