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Search results; Over 1,000 homes in Annapolis

Guest favourite
Apartment in Annapolis
Renovated Apt In Historic Dist w/2 Parking Spots
2 bedrooms, 3 beds, 1 private bathroom
28 Sept – 3 Oct
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4.94 out of 5 average rating, 453 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
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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
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Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
3–8 Dec
4.97 out of 5 average rating, 462 reviews
Top guest favourite
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds, 1 bathroom
29 Oct – 3 Nov
4.96 out of 5 average rating, 227 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 19 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
Eastport Oasis
5 bedrooms, 5 beds, 2 bathrooms
1–6 Nov
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
3–8 Oct
4.97 out of 5 average rating, 470 reviews
Guest favourite
Home in Annapolis
Admiral’s Landing: Walk to Naval Academy, West St.
3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 53 reviews
Top guest favourite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
3 bedrooms, 5 beds, 2.5 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 202 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
Guest house in Annapolis
Garden View, 1 Bedroom and a Loft.
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 166 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
Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds, 3.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 53 reviews
Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
1–6 Jan
4.96 out of 5 average rating, 262 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
4.99 out of 5 average rating, 69 reviews
Home in Pasadena
Bodkin Bay House
4 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Home in Annapolis
4 bedrooms, 7 beds, 3 bath completely updated
4 bedrooms, 7 beds, 3 bathrooms
11–16 Oct
4.97 out of 5 average rating, 146 reviews