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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
Studio, 1 bed, 1 private bathroom
1–6 Aug
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5.0 out of 5 average rating, 172 reviews
Home in Pasadena
Spacious Family Home in Pasadena
New place to stay, 3 bedrooms, 4 beds, 2.5 bathrooms
11–16 Aug
Home in Annapolis
Waterfront Gem w/ Dock: 2 Mi to Dwtn Annapolis!
New place to stay, 4 bedrooms, 6 beds, 3 bathrooms
1–6 Aug
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4.9 out of 5 average rating, 10 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
16–21 Aug
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
4.92 out of 5 average rating, 132 reviews, 3 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
4.95 out of 5 average rating, 182 reviews, 1 queen bed, 3 bathrooms
15–20 Aug
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 181 reviews, 1 queen bed, 1.5 bathrooms
16–21 Aug
Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
4.94 out of 5 average rating, 200 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
Top guest favourite
Home in Annapolis
CJ's Cottage
4.96 out of 5 average rating, 74 reviews, 2 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
5.0 out of 5 average rating, 93 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
10–15 Aug
Top guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
4.96 out of 5 average rating, 72 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Aug
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4.96 out of 5 average rating, 24 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
10–15 Aug
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 30 reviews, 3 bedrooms, 2 bathrooms
10–15 Aug
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 78 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
23–28 Aug
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 17 reviews, 4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
Guest favourite
Home in Annapolis
Peaceful Pet-Friendly Stay | Near USNA & Beaches
4.9 out of 5 average rating, 21 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Aug
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
4.86 out of 5 average rating, 73 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
4.95 out of 5 average rating, 139 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–15 Sept