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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
4.97 out of 5 average rating, 36 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
4.92 out of 5 average rating, 132 reviews, 3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Flat in Annapolis
The Sail Loft
5.0 out of 5 average rating, 36 reviews, 3 bedrooms, 4 beds, 2 bathrooms
25–30 Jul
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 76 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
30 Jul – 4 Aug
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4.97 out of 5 average rating, 39 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
21–26 Jul
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 28 reviews, 3 bedrooms, 2 bathrooms
13–18 Jul
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
4.92 out of 5 average rating, 89 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
13–18 Sept
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Jul
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 6 beds, 2 bathrooms
13–18 Jul
Top guest favourite
Home in Annapolis
Fenced + Fire Pit + Coffee Bar 2 miles from USNA
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
Top guest favourite
Home in Annapolis
Beautiful house in the best location!
4.96 out of 5 average rating, 47 reviews, 3 bedrooms, 6 beds, 3.5 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Annapolis
Historic 4BR Naptown Home <1 Mile to Stadium
4.98 out of 5 average rating, 66 reviews, 4 bedrooms, 8 beds, 3.5 bathrooms
13–18 Sept
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
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 4 bathrooms
14–19 Jul
Top guest favourite
Home in Annapolis
*Unique Entire Dwntwn Triplex *Parking*Sleeps12-18
5.0 out of 5 average rating, 26 reviews, 6 bedrooms, 9 beds, 6 bathrooms
17–23 Aug
Top guest favourite
Home in Annapolis
West street historic home
4.99 out of 5 average rating, 68 reviews, 5 bedrooms, 6 beds, 3 bathrooms
19–24 Jul
Guest favourite
Home in Arnold
Rachel's BnB
4.91 out of 5 average rating, 137 reviews, 2 bedrooms, 3 beds, 1 bathroom
26–31 Jul