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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Charming City Oasis. Walk to harbor, eateries.USNA
4 bedrooms, 4 beds, 2 private bathrooms
8–13 Sept
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4.87 out of 5 average rating, 116 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
16–21 Aug
4.93 out of 5 average rating, 184 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
1–6 Aug
4.98 out of 5 average rating, 161 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds
15–20 Aug
4.96 out of 5 average rating, 76 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
15–20 Aug
4.95 out of 5 average rating, 183 reviews
Home in Annapolis
DTA - Park and Walk in safe, quiet neighborhood
2 bedrooms, 2 queen beds
1–6 Aug
New place to stay
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
23–28 Aug
4.93 out of 5 average rating, 84 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds
23–28 Aug
4.95 out of 5 average rating, 142 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed
1–6 Aug
4.96 out of 5 average rating, 224 reviews
Room in Bowie
Cozy Private Queen Room | Free Parking | Near DC
1 queen bed
17–22 Aug
New place to stay
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 30 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
16–21 Aug
4.93 out of 5 average rating, 187 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
14–19 Aug
4.97 out of 5 average rating, 96 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
24–29 Aug
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 19 reviews
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed
16–21 Aug
4.9 out of 5 average rating, 359 reviews
Top guest favourite
Flat in Annapolis
Annapolis Main Street Modern Apartment
2 bedrooms, 2 queen beds
10–15 Aug
5.0 out of 5 average rating, 48 reviews