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Search results; Over 1,000 homes in Annapolis

Guest favourite
Home in Annapolis
Country House on the Bay
5 bedrooms, 10 beds, 3 private bathrooms
20–25 Jul
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4.9 out of 5 average rating, 223 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, 180 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
14–19 Aug
4.97 out of 5 average rating, 461 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
6–11 Jul
4.99 out of 5 average rating, 153 reviews
Top guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds
5–10 Jul
4.94 out of 5 average rating, 200 reviews
Guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds
18–23 Jul
4.96 out of 5 average rating, 71 reviews
Guest favourite
Flat in Annapolis
Annapolis 4 Steps to Harbor Backs to Gate 1
1 bedroom, 2 beds
5–10 Jul
4.96 out of 5 average rating, 27 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, 9 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds
12–17 Jul
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Home in Annapolis
Stunning Historic Annapolis Home, Steps to Academy
4 bedrooms, 5 beds
5–10 Jul
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
1 bedroom, 2 beds
10–15 Jul
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
16–21 Aug
4.97 out of 5 average rating, 93 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
16–21 Jul
4.92 out of 5 average rating, 71 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
27 Jul – 1 Aug
4.89 out of 5 average rating, 358 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds
11–16 Jul
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed
10–15 Aug
4.96 out of 5 average rating, 413 reviews
Guest favourite
Home in Edgewater
Sunset Corner House
3 bedrooms, 3 beds
27 Jul – 1 Aug
4.83 out of 5 average rating, 71 reviews
Top guest favourite
Room in Annapolis
Howard's Cove Retreat
2 single beds
13–18 Jul
4.92 out of 5 average rating, 533 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds
13–18 Jul
5.0 out of 5 average rating, 11 reviews