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Search results; Over 1,000 homes in Annapolis

Guest favourite
Home in Annapolis
Waterfront Oasis in Eastport-Easy Walk to Downtown
5 bedrooms, 8 beds, 3.5 private bathrooms
9–14 Aug
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4.93 out of 5 average rating, 122 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
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds
16–21 Aug
4.91 out of 5 average rating, 139 reviews
Guest favourite
Home in Annapolis
Peaceful Pet-Friendly Stay | Near USNA & Beaches
3 bedrooms, 5 beds
1–6 Aug
4.91 out of 5 average rating, 22 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 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
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
16–21 Aug
4.93 out of 5 average rating, 187 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
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
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
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
10–15 Aug
4.89 out of 5 average rating, 365 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
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
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
Charming Annapolis Townhome
2 bedrooms
24–29 Aug
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
23–28 Aug
4.93 out of 5 average rating, 81 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, 100 reviews
Guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms, 3 beds
11–16 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Edgewater
Spacious 3 Bedrooms House+Patio+Playground
3 bedrooms, 3 beds
23–28 Aug
4.93 out of 5 average rating, 210 reviews