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Search results; Over 1,000 homes in Annapolis

Descriptions are based on details hosts provide
Guest favourite
Home in Annapolis
Country House on the Bay
5 bedrooms, 10 beds, 3 private bathrooms
20–25 Jul
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4.9 out of 5 average rating, 225 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 179 reviews, 1 queen bed, 1.5 bathrooms
1–6 Aug
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 76 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
30 Jul – 4 Aug
Top guest favourite
Loft in Annapolis
Exposed brick loft on Main Street
4.92 out of 5 average rating, 1125 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Cottage in Annapolis
Mill Creek views from a wooded porch
4.97 out of 5 average rating, 463 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug
Guest favourite
Home in Arnold
Egyptian cotton linens near downtown Annapolis
4.91 out of 5 average rating, 137 reviews, 2 bedrooms, 3 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in Annapolis
Federal-style home with a private courtyard
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 4 bathrooms
16–21 Jul
Top guest favourite
Home in Annapolis
1911 Victorian 5 blocks from Main St
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
31 Jul – 5 Aug
Top guest favourite
Cottage in Annapolis
1910 waterfront cottage with a private dock
4.98 out of 5 average rating, 159 reviews, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Home in Annapolis
CJ's Cottage
4.96 out of 5 average rating, 73 reviews, 2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 183 reviews, 1 queen bed, 1.5 bathrooms
10–15 Aug
Top guest favourite
Home in Annapolis
Fire pit and fireplace near downtown
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Guest favourite
Flat in Annapolis
Quiet private entrance near downtown Annapolis
4.89 out of 5 average rating, 361 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
5.0 out of 5 average rating, 171 reviews, 1 bed, 1 bathroom
15–20 Jul
Top guest favourite
Home in Stevensville
Waterfront with swim spa, sauna, and dock
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
4.9 out of 5 average rating, 355 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Home in Annapolis
Retro Eastport home, walkable to downtown
4.95 out of 5 average rating, 80 reviews, 4 bedrooms, 4 beds, 2 bathrooms
24–29 Jul
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
4.96 out of 5 average rating, 223 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
Guest favourite
Home in Annapolis
Home theater and outdoor fireplace in Annapolis
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 7 beds, 3 bathrooms
26–31 Jul