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Search results; Over 1,000 homes in Annapolis

Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
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4.9 out of 5 average rating, 361 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
29 Aug – 3 Sept
4.98 out of 5 average rating, 163 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
16–21 Aug
4.97 out of 5 average rating, 97 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
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
16–21 Aug
4.93 out of 5 average rating, 188 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
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
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 Annapolis
Modern Annapolis Getaway - 2 Free Parking Spaces
2 bedrooms, 2 double beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 117 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed
10–15 Aug
4.9 out of 5 average rating, 49 reviews
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
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
Home in Annapolis
Annapolis House near Naval Academy
4 bedrooms, 4 beds
12–17 Aug
New place to stay
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
6–11 Sept
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds
13–18 Aug
4.96 out of 5 average rating, 76 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed
24–29 Aug
4.96 out of 5 average rating, 422 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
King George Downtown Annapolis Getaway
2 bedrooms, 2 beds
10–15 Aug
4.86 out of 5 average rating, 125 reviews
Top guest favourite
Home in Annapolis
Fenced + Fire Pit + Coffee Bar 2 miles from USNA
4 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 13 reviews