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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
17–22 Jul
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4.89 out of 5 average rating, 431 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
30 Jul – 4 Aug
4.92 out of 5 average rating, 78 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
10–15 Aug
4.93 out of 5 average rating, 183 reviews
Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed
17–22 Jul
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
1 bed
17–22 Jul
5.0 out of 5 average rating, 171 reviews
Top guest favourite
Home in Annapolis
Quaint in the Heart of Annapolis
2 bedrooms, 2 double beds
24–29 Jul
5.0 out of 5 average rating, 114 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds
21–26 Jul
4.96 out of 5 average rating, 111 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
17–22 Jul
4.97 out of 5 average rating, 463 reviews
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms, 4 beds
19–24 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
3 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 52 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
26–31 Jul
4.95 out of 5 average rating, 182 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
26–31 Jul
4.98 out of 5 average rating, 160 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
10–15 Aug
4.89 out of 5 average rating, 362 reviews
Top guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds
24–29 Jul
4.95 out of 5 average rating, 80 reviews
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds
23–28 Aug
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed
21–26 Jul
4.96 out of 5 average rating, 130 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds
13–18 Aug
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds
19–24 Jul
4.96 out of 5 average rating, 73 reviews
Superhost
Flat in Annapolis
Modern Eastport Getaway, Near Historic Annapolis
1 bedroom, 3 beds
19–24 Jul
4.84 out of 5 average rating, 19 reviews