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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 beds, 1 private bathroom
14–19 Aug
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4.97 out of 5 average rating, 466 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
4.97 out of 5 average rating, 96 reviews, 2 beds, 1 bathroom
14–19 Aug
Guest favourite
Home in Arnold
Rachel's BnB
4.91 out of 5 average rating, 140 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.93 out of 5 average rating, 82 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
23–28 Aug
Top guest favourite
Flat in Annapolis
Serene Hideaway
5.0 out of 5 average rating, 30 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
4.89 out of 5 average rating, 365 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Home in Annapolis
DTA - Park and Walk in safe, quiet neighborhood
New place to stay, 2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Aug
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
4.98 out of 5 average rating, 62 reviews, 2 bedrooms, 1.5 bathrooms
24–29 Aug
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
4.97 out of 5 average rating, 39 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Aug
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 16 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
4.96 out of 5 average rating, 131 reviews, 1 queen bed, 1 bathroom
2–7 Aug
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.94 out of 5 average rating, 31 reviews, 3 bedrooms, 2 bathrooms
10–15 Aug
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
4.96 out of 5 average rating, 224 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
4.98 out of 5 average rating, 66 reviews, 3 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Boat in Annapolis
Welcome Aboard!
4.96 out of 5 average rating, 112 reviews, 2 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 19 reviews, 4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 3 beds, 2 bathrooms
19–24 Aug
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
4.98 out of 5 average rating, 161 reviews, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 181 reviews, 1 queen bed, 1.5 bathrooms
16–21 Aug