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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
2 bedrooms, 2 beds, 1 private bathroom
9–14 Sept
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4.96 out of 5 average rating, 126 reviews
Guest favourite
Home in Annapolis
The Corner House-Annapolis
3 bedrooms, 5 beds
8–13 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 3 beds
12–17 Sept
4.92 out of 5 average rating, 524 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
20–25 Sept
4.91 out of 5 average rating, 92 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
13–18 Sept
4.98 out of 5 average rating, 165 reviews
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds
8–13 Sept
5.0 out of 5 average rating, 146 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed
17–22 Oct
5.0 out of 5 average rating, 226 reviews
Top guest favourite
Home in Annapolis
3BR/2BA Annapolis Cottage
3 bedrooms, 4 beds
8–13 Sept
4.98 out of 5 average rating, 226 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
20–25 Sept
4.95 out of 5 average rating, 191 reviews
Top guest favourite
Flat in Annapolis
Perfect Eastport location
2 bedrooms, 3 beds
8–13 Sept
4.98 out of 5 average rating, 147 reviews
Guest favourite
Home in Annapolis
Family Oasis|Spa Shower|Near USNA stadium & DTA
3 bedrooms, 5 beds
8–13 Sept
5.0 out of 5 average rating, 20 reviews
Hotel in Annapolis
Close to U.S. Naval Academy + Breakfast. Pool. Gym
1 bedroom, 1 king bed
8–13 Sept
4.5 out of 5 average rating, 28 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
20–25 Sept
4.93 out of 5 average rating, 194 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
3–8 Oct
4.97 out of 5 average rating, 470 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 174 reviews
Guest favourite
Home in Annapolis
Admiral’s Landing: Walk to Naval Academy, West St.
3 bedrooms, 3 beds
13–18 Sept
4.98 out of 5 average rating, 53 reviews
Top guest favourite
Cottage in Annapolis
Charming City Oasis. Walk to harbor, eateries.USNA
4 bedrooms, 4 beds
8–13 Sept
4.87 out of 5 average rating, 117 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
4–9 Oct
4.89 out of 5 average rating, 371 reviews
Top guest favourite
Guest suite in Arnold
Coastal Comfort Retreat near Annapolis, EV charger
1 bedroom, 2 beds
13–18 Sept
4.94 out of 5 average rating, 226 reviews