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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
Studio, 1 bed, 1 private bathroom
1–6 Sept
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4.98 out of 5 average rating, 163 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
19–24 Aug
4.92 out of 5 average rating, 61 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed, 1 bathroom
19–24 Aug
4.9 out of 5 average rating, 50 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 188 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 362 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.94 out of 5 average rating, 143 reviews
Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed, 1 bathroom
20–25 Aug
4.95 out of 5 average rating, 210 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.92 out of 5 average rating, 1133 reviews
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds, 2.5 bathrooms
19–24 Aug
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 97 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds, 2.5 bathrooms
24–29 Aug
4.94 out of 5 average rating, 32 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
20–25 Sept
4.95 out of 5 average rating, 187 reviews
Top guest favourite
Guest house in Annapolis
Garden View, 1 Bedroom and a Loft.
2 bedrooms, 3 beds, 1 bathroom
19–24 Aug
4.99 out of 5 average rating, 165 reviews
Home in Annapolis
Gracie's Gallery & Garden in Annapolis
4 bedrooms, 6 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 114 reviews
Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed, 1 bathroom
20–25 Aug
5.0 out of 5 average rating, 47 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, 2 bathrooms
29 Aug – 3 Sept
4.89 out of 5 average rating, 27 reviews
Guest favourite
Home in Annapolis
Pet-Friendly Annapolis Getaway | USNA & Beach/Bay
3 bedrooms, 5 beds, 2.5 bathrooms
23–28 Aug
4.91 out of 5 average rating, 23 reviews
Top guest favourite
Room in Severna Park
Severna Park Private Entry Suite
2 beds, 1 bathroom
20–25 Aug
4.98 out of 5 average rating, 64 reviews