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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Charming Waterfront Cottage on Historic Property
2 bedrooms, 3 beds, 1.5 private bathrooms
1–6 Aug
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4.95 out of 5 average rating, 64 reviews
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
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
4.97 out of 5 average rating, 39 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Aug
Guest favourite
Home in Annapolis
Peaceful Pet-Friendly Stay | Near USNA & Beaches
4.91 out of 5 average rating, 22 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Aug
Guest favourite
Home in Arnold
Rachel's BnB
4.91 out of 5 average rating, 139 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
4.94 out of 5 average rating, 31 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
10–15 Aug
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
4.98 out of 5 average rating, 66 reviews, 3 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Home in Riva
Charming Bright Spacious 3BR 2BT near South River
4.89 out of 5 average rating, 72 reviews, 3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
Guest favourite
Home in Annapolis
Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths
4.96 out of 5 average rating, 148 reviews, 3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
4.89 out of 5 average rating, 365 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
4.98 out of 5 average rating, 62 reviews, 2 bedrooms, 1.5 bathrooms
24–29 Aug
Guest favourite
Home in Annapolis
Stay Retro Naptown
4.95 out of 5 average rating, 80 reviews, 4 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
Guest favourite
Home in Annapolis
Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit
4.97 out of 5 average rating, 100 reviews, 3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
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
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 19 reviews, 4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
5.0 out of 5 average rating, 17 reviews, 4 bedrooms, 4 beds, 4 bathrooms
9–14 Aug
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 187 reviews, 1 queen bed, 1.5 bathrooms
16–21 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
Guest favourite
Home in Annapolis
Marymont Cottage
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 3 beds, 2 bathrooms
11–16 Aug