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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 beds, 1 private bathroom
14–19 Aug
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4.97 out of 5 average rating, 466 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 79 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
23–28 Aug
Top guest favourite
Home in Annapolis
CJ's Cottage
4.96 out of 5 average rating, 75 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
4.96 out of 5 average rating, 224 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 18 reviews, 4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
4.94 out of 5 average rating, 201 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
Top guest favourite
Boat in Annapolis
Welcome Aboard!
4.96 out of 5 average rating, 111 reviews, 2 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
Home in Annapolis
DTA - Park and Walk in safe, quiet neighborhood
New place to stay, 2 bedrooms, 2 beds, 1.5 bathrooms
1–6 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
Superhost
Home in Annapolis
*NEW* Pristine, Upscale, Walkable to Town/Stadium
New place to stay, 3 bedrooms, 4 beds, 3.5 bathrooms
19–24 Aug
Guest favourite
Home in Arnold
Rachel's BnB
4.91 out of 5 average rating, 137 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
4.95 out of 5 average rating, 140 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–15 Sept
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
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
Top guest favourite
Home in Annapolis
2Bd Water View, w/Beach near Downtown Annapolis
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 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 suite in Annapolis
The Harness Creek Retreat
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 1 bathroom
10–15 Aug
Top guest favourite
Guest house in Annapolis
"The Perch" - Hot Tub - Beach - Chesapeake Bay
4.91 out of 5 average rating, 96 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Room in Annapolis
Lovely Private Master Bedroom
4.98 out of 5 average rating, 247 reviews, 1 queen bed, 1 bathroom
1–6 Aug