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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Townhouse in Annapolis
Moose’s Happy Place
3 bedrooms, 4 beds, 3.5 shared bathrooms
24–29 Nov
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5.0 out of 5 average rating, 113 reviews
Top guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
5.0 out of 5 average rating, 28 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
10–15 Aug
4.89 out of 5 average rating, 359 reviews
Top guest favourite
Flat in Annapolis
Perfect Eastport location
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.98 out of 5 average rating, 143 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
19–24 Jul
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
4.97 out of 5 average rating, 73 reviews
Top guest favourite
Home in Annapolis
Gorgeous Historic Downtown Annapolis House
5 bedrooms, 9 beds, 3.5 bathrooms
5–10 Jul
4.98 out of 5 average rating, 155 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 354 reviews
Superhost
Flat in Annapolis
Gybeset Eastport Inn
3 bedrooms, 3 beds, 1 bathroom
6–11 Jul
4.88 out of 5 average rating, 303 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.97 out of 5 average rating, 454 reviews
Guest favourite
Place to stay in Annapolis
Chesapeake Bay View 3BR/2BA Duplex*HOT TUB*
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.94 out of 5 average rating, 127 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
10–15 Aug
4.92 out of 5 average rating, 1122 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 bathrooms
30 Jul – 4 Aug
4.96 out of 5 average rating, 111 reviews
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium- Renovated 2BR Downtown
2 bedrooms, 4 beds, 1.5 bathrooms
20–25 Jul
4.86 out of 5 average rating, 72 reviews
Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
16–21 Jul
4.92 out of 5 average rating, 73 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds, 3.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 89 reviews
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.96 out of 5 average rating, 256 reviews