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Search results; Over 1,000 homes in Annapolis

Guest favourite
Room in Annapolis
Cozy private room in Annapolis home
1 bedroom, 1 bed, 1 shared bathroom
1–6 Aug
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4.84 out of 5 average rating, 478 reviews
Home in Pasadena
Spacious Family Home in Pasadena
3 bedrooms, 4 beds, 2.5 bathrooms
11–16 Aug
New place to stay
Home in Annapolis
Waterfront Gem w/ Dock: 2 Mi to Dwtn Annapolis!
4 bedrooms, 6 beds, 3 bathrooms
1–6 Aug
New place to stay
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
4.96 out of 5 average rating, 75 reviews
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
4.92 out of 5 average rating, 132 reviews
Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
4.94 out of 5 average rating, 200 reviews
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
1 bedroom, 2 beds, 1.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 93 reviews
Top guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Aug
4.96 out of 5 average rating, 72 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
4.95 out of 5 average rating, 22 reviews
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds, 2.5 bathrooms
10–15 Aug
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 bathroom
9–15 Sept
4.95 out of 5 average rating, 139 reviews
Guest favourite
Home in Annapolis
Peaceful Pet-Friendly Stay | Near USNA & Beaches
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Aug
4.9 out of 5 average rating, 21 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
4–9 Aug
4.93 out of 5 average rating, 181 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
4.98 out of 5 average rating, 66 reviews