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Search results; Over 1,000 homes in Annapolis

Guest favourite
Apartment in Annapolis
Renovated Apt In Historic Dist w/2 Parking Spots
2 bedrooms, 3 beds, 1 private bathroom
9–14 Aug
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4.94 out of 5 average rating, 444 reviews
Home in Pasadena
Spacious Family Home in Pasadena
3 bedrooms, 4 beds, 2.5 bathrooms
11–16 Aug
New place to stay
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
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
15–20 Aug
4.95 out of 5 average rating, 182 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
23–28 Aug
4.92 out of 5 average rating, 78 reviews
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 Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
16–21 Aug
4.9 out of 5 average rating, 10 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
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
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
4.96 out of 5 average rating, 111 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.96 out of 5 average rating, 224 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
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
Home in Annapolis
Fleet St Retreat in Downtown - Great Location!
2 bedrooms, 3 beds, 2.5 bathrooms
9–14 Aug
4.91 out of 5 average rating, 120 reviews
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
10–15 Aug
4.94 out of 5 average rating, 31 reviews
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.86 out of 5 average rating, 73 reviews
Top guest favourite
Guest house in Annapolis
"The Perch" - Hot Tub - Beach - Chesapeake Bay
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 96 reviews