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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Secluded Cottage_ A+ Amenities in Historic Dwntwn
2 bedrooms, 3 beds, 1 private bathroom
15–20 Jul
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4.93 out of 5 average rating, 224 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 179 reviews, 1 queen bed, 1.5 bathrooms
1–6 Aug
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
4.89 out of 5 average rating, 361 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Flat in Annapolis
Perfect Eastport location
4.98 out of 5 average rating, 144 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
4.92 out of 5 average rating, 1123 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
4.96 out of 5 average rating, 245 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Oct
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
4.98 out of 5 average rating, 58 reviews, 2 bedrooms, 1.5 bathrooms
19–24 Jul
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
4.98 out of 5 average rating, 158 reviews, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
4.96 out of 5 average rating, 130 reviews, 1 queen bed, 1 bathroom
21–26 Jul
Superhost
Home in Annapolis
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
4.85 out of 5 average rating, 27 reviews, 3 bedrooms, 9 beds, 3.5 bathrooms
13–18 Jul
Top guest favourite
Home in Annapolis
Peaceful Waterfront Home in Annapolis 3BR 2BA.
4.99 out of 5 average rating, 79 reviews, 3 bedrooms, 4 beds, 2 bathrooms
24–29 Jul
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
4.97 out of 5 average rating, 455 reviews, 1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec
Top guest favourite
Home in Annapolis
Gorgeous Historic Downtown Annapolis House
4.98 out of 5 average rating, 156 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
13–18 Jul
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 463 reviews, 2 bedrooms, 2 beds, 1 bathroom
24–29 Aug
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
4.96 out of 5 average rating, 416 reviews, 1 queen bed, 1 bathroom
17–22 Aug
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 181 reviews, 1 queen bed, 1.5 bathrooms
24–29 Jul
Guest favourite
Flat in Annapolis
Annapolis 4 Steps to Harbor Backs to Gate 1
4.96 out of 5 average rating, 27 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Superhost
Flat in Annapolis
Gybeset Eastport Inn
4.88 out of 5 average rating, 303 reviews, 3 bedrooms, 3 beds, 1 bathroom
23–28 Aug