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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 private bathroom
9–14 Sept
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4.95 out of 5 average rating, 142 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
17–22 Aug
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 469 reviews
Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed, 1 bathroom
17–22 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, 1132 reviews
Home in Pasadena
Cozy Riviera Beach Retreat Near BWI & Annapolis
3 bedrooms, 5 beds, 1.5 bathrooms
21–26 Aug
New place to stay
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
6–11 Sept
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 97 reviews
Top guest favourite
Flat in Severna Park
Welcome to Anchors Aweigh!
1 bedroom, 3 beds, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 88 reviews
Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 3 beds, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 520 reviews
Top guest favourite
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds, 1 bathroom
25–30 Aug
5.0 out of 5 average rating, 5 reviews
Home in Annapolis
DTA - Park and Walk in safe, quiet neighborhood
2 bedrooms, 2 queen beds, 1.5 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
4.96 out of 5 average rating, 114 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
23–28 Aug
4.93 out of 5 average rating, 85 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 50 reviews
Home in Annapolis
City Gate Sanctuary
4 bedrooms, 4 beds, 3.5 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Home in Edgewater
Annapolis Area Waterside Retreat
4 bedrooms, 4 queen beds, 2 bathrooms
22–27 Aug
4.95 out of 5 average rating, 256 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
23–28 Aug
4.93 out of 5 average rating, 190 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 23 reviews