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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Apartment in Annapolis
Annapolis Condo-1 bedroom King
1 bedroom, 3 beds, 1 private bathroom
23–28 Aug
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4.97 out of 5 average rating, 127 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
Guest favourite
Townhouse in Annapolis
Annapolis Downtown Pleasant St Townhome 3 bedrooms
3 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
4.91 out of 5 average rating, 195 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
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
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
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
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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
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
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
Top guest favourite
Home in Annapolis
Large Priv. Suite Near D-town Annapolis & Stadium
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 32 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
Top guest favourite
Guest house in Stevensville
Private Guesthouse | 7-acres | Near wedding venues
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 24 reviews
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
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
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds, 1.5 bathrooms
17–22 Aug
4.86 out of 5 average rating, 74 reviews
Top guest favourite
Home in Annapolis
Downtown Annapolis Home
4 bedrooms, 5 beds, 2.5 bathrooms
17–22 Aug
4.99 out of 5 average rating, 100 reviews
Top guest favourite
Guest house in Annapolis
Walk to City Dock & USNA | Designer Eastport Home
2 bedrooms, 3 beds, 1 bathroom
17–22 Aug
4.98 out of 5 average rating, 44 reviews