
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
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Popular amenities for Annapolis holiday rentals
Other great holiday rentals in Annapolis
Guest favourite

Flat in Annapolis
4.96 out of 5 average rating, 98 reviewsHistoric Annapolis Rental Minutes from Downtown
Guest favourite

Flat in Annapolis
5 out of 5 average rating, 26 reviewsElegant Uptown Condo withParking
Top guest favourite

Home in Annapolis
5 out of 5 average rating, 59 reviewsDowntown Annapolis Home
Guest favourite

Home in Crownsville
4.94 out of 5 average rating, 16 reviewsWelcome to Heron House! Annapolis Waterfront Oasis
Top guest favourite

Home in Annapolis
5 out of 5 average rating, 25 reviewsThe Midship Quarters
Top guest favourite

Home in Annapolis
5 out of 5 average rating, 44 reviewsBay Home in Annapolis with Private Dock
Top guest favourite

Apartment in Annapolis
4.96 out of 5 average rating, 95 reviewsFunky Uptown Apt meets Downtown - Hist District
Top guest favourite

Flat in Annapolis
4.97 out of 5 average rating, 36 reviewsAnnapolis Main Street View Apartment
Quick stats about holiday rentals in Annapolis
Total rentals
650 properties
Total number of reviews
32K reviews
Family-friendly rentals
460 properties are a good fit for families
Pet-friendly rentals
200 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
350 properties have a dedicated workspace
Destinations to explore
- Washington Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Jersey Shore Holiday rentals
- Pocono Mountains Holiday rentals
- New York Holiday rentals
- East River Holiday rentals
- Plainview Holiday rentals
- Long Island Holiday rentals
- Outer Banks Holiday rentals
- Hudson Valley Holiday rentals
- The Hamptons Holiday rentals
- Fitness-friendly rentals Annapolis
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- Nationals Park
- The White House
- National Mall
- Betterton Beach
- Georgetown University
- District Wharf
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Smithsonian National Museum of Natural History
- Hampden
- M&T Bank Stadium
- Sandy Point State Park
- Arlington National Cemetery
- Patterson Park
- Georgetown Waterfront Park
- Washington Monument
- National Harbor
- Great Falls Park
- National Air and Space Museum
- Maryland Renaissance Festival
- Smithsonian American Art Museum
- Lincoln Park
- Crystal Beach Manor, Earleville, MD
- Six Flags America