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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
Studio, 1 bed, 1 private bathroom
1–6 Aug
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4.98 out of 5 average rating, 161 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
23–28 Aug
4.92 out of 5 average rating, 79 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds
15–20 Aug
4.96 out of 5 average rating, 75 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds
10–15 Aug
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed
1–6 Aug
4.96 out of 5 average rating, 224 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
15–20 Aug
4.95 out of 5 average rating, 182 reviews
Superhost
Home in Annapolis
*NEW* Pristine, Upscale, Walkable to Town/Stadium
3 bedrooms, 4 beds
19–24 Aug
New place to stay
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds
18–23 Aug
4.96 out of 5 average rating, 111 reviews
Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds
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
1–6 Aug
4.96 out of 5 average rating, 72 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, 15 reviews
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds
9–14 Aug
4.92 out of 5 average rating, 132 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds
9–15 Sept
4.95 out of 5 average rating, 140 reviews
Top guest favourite
Home in Annapolis
2Bd Water View, w/Beach near Downtown Annapolis
2 bedrooms, 3 beds
22–27 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Guest house in Annapolis
"The Perch" - Hot Tub - Beach - Chesapeake Bay
1 bedroom, 1 queen bed
9–14 Aug
4.91 out of 5 average rating, 96 reviews
Top guest favourite
Room in Annapolis
Lovely Private Master Bedroom
1 queen bed
1–6 Aug
4.98 out of 5 average rating, 247 reviews
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds
10–15 Aug
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
10–15 Aug
4.94 out of 5 average rating, 31 reviews