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Search results; Over 1,000 homes in Annapolis

Guest favourite
Flat in Annapolis
Dazzling day/night water views,1st class amemities
2 bedrooms, 3 beds, 1 private bathroom
31 Aug – 5 Sept
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4.92 out of 5 average rating, 106 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 469 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
4.93 out of 5 average rating, 85 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
6–11 Sept
4.94 out of 5 average rating, 187 reviews
Superhost
Home in Annapolis
5BR I Charming home Steps from USNA & Downtown
5 bedrooms, 6 beds, 4 bathrooms
31 Oct – 5 Nov
New place to stay
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, 2 bathrooms
16–21 Aug
4.88 out of 5 average rating, 26 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.92 out of 5 average rating, 1132 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
6–11 Sept
4.98 out of 5 average rating, 63 reviews
Home in Annapolis
City Gate Sanctuary
4 bedrooms, 4 beds, 3.5 bathrooms
16–21 Aug
New place to stay
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds, 2.5 bathrooms
12–17 Aug
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 32 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 189 reviews
Guest favourite
Home in Riva
Waterfront Annapolis Getaway!
1 bedroom, 1 king bed, 2.5 bathrooms
7–12 Sept
4.92 out of 5 average rating, 95 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed, 1 bathroom
12–17 Aug
4.9 out of 5 average rating, 49 reviews
Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
23–28 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
29 Aug – 3 Sept
4.98 out of 5 average rating, 163 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
20–25 Sept
4.95 out of 5 average rating, 186 reviews
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds, 1.5 bathrooms
17–22 Aug
4.86 out of 5 average rating, 74 reviews