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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
Studio, 1 bed, 1 private bathroom
29 Aug – 3 Sept
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4.98 out of 5 average rating, 163 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 31 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
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds
16–21 Aug
4.92 out of 5 average rating, 25 reviews
Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed
11–16 Aug
4.95 out of 5 average rating, 209 reviews
Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 3 beds
16–21 Aug
4.92 out of 5 average rating, 520 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, 21 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed
9–14 Aug
4.9 out of 5 average rating, 48 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds
10–15 Aug
4.99 out of 5 average rating, 68 reviews
Guest favourite
Home in Riva
Waterfront Annapolis Getaway!
1 bedroom, 1 king bed
7–12 Sept
4.92 out of 5 average rating, 95 reviews
Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds
16–21 Aug
4.94 out of 5 average rating, 202 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed
9–14 Aug
4.96 out of 5 average rating, 224 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
20–25 Sept
4.95 out of 5 average rating, 184 reviews
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, 17 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
23–28 Aug
4.96 out of 5 average rating, 167 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
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds
15–20 Sept
4.95 out of 5 average rating, 81 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds
18–23 Aug
4.96 out of 5 average rating, 113 reviews
Top guest favourite
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
3 bedrooms, 3 beds
10–15 Aug
4.97 out of 5 average rating, 152 reviews