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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
Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
4.94 out of 5 average rating, 201 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
4.96 out of 5 average rating, 75 reviews
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds, 2 bathrooms
9–14 Aug
4.92 out of 5 average rating, 132 reviews
Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.91 out of 5 average rating, 138 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
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, 3.5 bathrooms
19–24 Aug
New place to stay
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds, 2 bathrooms
15–20 Sept
4.95 out of 5 average rating, 80 reviews
Guest favourite
Home in Annapolis
Peaceful Pet-Friendly Stay | Near USNA & Beaches
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Aug
4.9 out of 5 average rating, 21 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds, 2 bathrooms
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, 1.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 181 reviews
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds, 2.5 bathrooms
10–15 Aug
4.96 out of 5 average rating, 24 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds, 2.5 bathrooms
10–15 Aug
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Home in Annapolis
Charming 4BR, 3BA Steps from the water.
4 bedrooms, 5 beds, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 58 reviews
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.86 out of 5 average rating, 74 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.96 out of 5 average rating, 224 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Annapolis
Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit
3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 98 reviews