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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 private bathroom
25–30 Oct
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4.97 out of 5 average rating, 237 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
29 Jun – 4 Jul
4.99 out of 5 average rating, 151 reviews
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
1 bedroom, 2 beds, 1.5 bathrooms
21–26 Jun
5.0 out of 5 average rating, 86 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
19–24 Jul
4.91 out of 5 average rating, 67 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
28 Jun – 3 Jul
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds, 1 bathroom
4–9 Jul
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
29 Jul – 3 Aug
4.92 out of 5 average rating, 1117 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
28 Jun – 3 Jul
4.95 out of 5 average rating, 178 reviews
Top guest favourite
Home in Annapolis
Downtown Annapolis Home
4 bedrooms, 5 beds, 2.5 bathrooms
22–27 Jun
4.99 out of 5 average rating, 91 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Annapolis
1 Block to USNA Stadium: Modern Annapolis Home!
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Annapolis
Quaint in the Heart of Annapolis
2 bedrooms, 2 double beds, 1 bathroom
19–24 Jun
5.0 out of 5 average rating, 111 reviews
Guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
5–10 Jul
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Home in Annapolis
Peaceful Waterfront Home in Annapolis 3BR 2BA.
3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
4.99 out of 5 average rating, 75 reviews
Superhost
Home in Edgewater
Chesapeake Bay Views with Deck & Beach Access
3 bedrooms, 6 beds, 2 bathrooms
21–26 Jun
New place to stay
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
6–11 Jul
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 210 reviews
Top guest favourite
Guest suite in Annapolis
Air Show and Tall Ships (Balt) - Stay in Annapolis
1 bedroom, 2 beds, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 bathrooms
26 Jun – 1 Jul
4.97 out of 5 average rating, 35 reviews