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Search results; Over 1,000 homes in Annapolis

Guest favourite
Home in Annapolis
The Corner House-Annapolis
3 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Annapolis
Family Oasis|Spa Shower|Near USNA stadium & DTA
3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 20 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
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
8–13 Sept
4.98 out of 5 average rating, 226 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, 147 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, 24 reviews
Guest favourite
Home in Annapolis
Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths
3 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.96 out of 5 average rating, 150 reviews
Guest favourite
Home in Annapolis
West Annapolis Cottage- 6BR Walk to Navy Stadium
6 bedrooms, 10 beds, 5 bathrooms
8–13 Sept
4.97 out of 5 average rating, 89 reviews
Top guest favourite
Flat in Annapolis
Perfect Eastport location
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 147 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
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, 191 reviews
Superhost
Home in Annapolis
Oasis by the Bay - Waterfront Heated Pool Hot Tub!
6 bedrooms, 8 beds, 5 bathrooms
20–25 Sept
4.86 out of 5 average rating, 22 reviews
Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds, 2 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 42 reviews
Guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 136 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 52 reviews
Superhost
Flat in Annapolis
Gybeset Eastport Inn
3 bedrooms, 3 beds, 1 bathroom
26–31 Oct
4.88 out of 5 average rating, 306 reviews
Guest favourite
Home in Annapolis
Waterfront Oasis in Eastport-Easy Walk to Downtown
5 bedrooms, 8 beds, 3.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 124 reviews