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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest suite in Annapolis
Independent Access Garage Apartment, Near Downtown
1 bedroom, 1 bed, 1 private bathroom
15–20 Aug
,
4.89 out of 5 average rating, 432 reviews
Home in Pasadena
Cozy Riviera Beach Retreat Near BWI & Annapolis
3 bedrooms, 3 beds
12–17 Aug
New place to stay
Superhost
Home in Annapolis
5BR I Charming home Steps from USNA & Downtown
5 bedrooms, 6 beds
31 Oct – 5 Nov
New place to stay
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 469 reviews
Home in Annapolis
City Gate Sanctuary
4 bedrooms, 4 beds
16–21 Aug
New place to stay
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, 85 reviews
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed
16–21 Aug
4.96 out of 5 average rating, 134 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
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds
14–19 Aug
4.94 out of 5 average rating, 31 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
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, 18 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed
11–16 Aug
4.9 out of 5 average rating, 49 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
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, 185 reviews
Top guest favourite
Home in Annapolis
Fenced + Fire Pit + Coffee Bar 2 miles from USNA
4 bedrooms, 4 beds
11–16 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed
20–25 Sept
4.9 out of 5 average rating, 361 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
6–11 Sept
4.94 out of 5 average rating, 187 reviews
Top guest favourite
Guest house in Stevensville
Private Guesthouse | 7-acres | Near wedding venues
2 bedrooms, 3 beds
11–16 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
6–11 Sept
4.98 out of 5 average rating, 63 reviews