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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 private bathrooms
26 Sept – 1 Oct
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4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Annapolis
The Corner House-Annapolis
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Annapolis
Mast & Main | Steps to City Dock & Naval Academy
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
New place to stay
Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 3 beds, 1 bathroom
12–17 Sept
4.92 out of 5 average rating, 524 reviews
Top guest favourite
Home in Annapolis
3BR/2BA Annapolis Cottage
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 226 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
20–25 Sept
4.93 out of 5 average rating, 194 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
20–25 Sept
4.95 out of 5 average rating, 190 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds, 3.5 bathrooms
20–25 Sept
4.91 out of 5 average rating, 92 reviews
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 146 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 174 reviews
Guest favourite
Home in Annapolis
Family Oasis|Spa Shower|Near USNA stadium & DTA
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 20 reviews
Guest favourite
Flat in Annapolis
Uptown Condo w 2 Parking Spots
1 bedroom, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 66 reviews
Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom, 2 beds, 1.5 bathrooms
25–30 Oct
4.98 out of 5 average rating, 105 reviews
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
3 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 14 reviews
Guest favourite
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Room in Annapolis
Quiet-Home Annapolis
1 bed, 2 bathrooms
7–12 Sept
4.85 out of 5 average rating, 106 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 33 reviews