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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 private bathroom
23–28 Aug
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4.95 out of 5 average rating, 140 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
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
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
Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds
16–21 Aug
4.91 out of 5 average rating, 138 reviews
Guest favourite
Home in Annapolis
Peaceful Pet-Friendly Stay | Near USNA & Beaches
3 bedrooms, 5 beds
1–6 Aug
4.9 out of 5 average rating, 21 reviews
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds
15–20 Sept
4.95 out of 5 average rating, 80 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
Home in Riva
Charming Bright Spacious 3BR 2BT near South River
3 bedrooms, 4 beds
9–14 Aug
4.89 out of 5 average rating, 72 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds
10–15 Aug
4.98 out of 5 average rating, 66 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
16–21 Aug
4.93 out of 5 average rating, 181 reviews
Superhost
Home in Annapolis
*NEW* Pristine, Upscale, Walkable to Town/Stadium
3 bedrooms, 4 beds
29 Sept – 4 Oct
New place to stay
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
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds
10–15 Aug
4.94 out of 5 average rating, 31 reviews
Guest favourite
Guest suite in Annapolis
Quaint 2BR Naptown Hidden Gem<1 Mile-Navy Stadium
2 bedrooms, 4 beds
10–15 Aug
4.91 out of 5 average rating, 57 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
Guest favourite
Home in Annapolis
Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit
3 bedrooms, 4 beds
16–21 Aug
4.97 out of 5 average rating, 98 reviews
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, 19 reviews
Guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms, 3 beds
11–16 Aug
5.0 out of 5 average rating, 28 reviews