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Search results; Over 1,000 homes in Annapolis

Guest favourite
Apartment in Annapolis
Anchors Away
Studio, 1 bed, 1 private bathroom
16–21 Jul
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4.84 out of 5 average rating, 101 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 78 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
30 Jul – 4 Aug
Home in Pasadena
Spacious Family Home in Pasadena
New place to stay, 3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Jul
Top guest favourite
Flat in Annapolis
Serene Hideaway
5.0 out of 5 average rating, 27 reviews, 1 bedroom, 2 beds, 1 bathroom
11–16 Aug
Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
5.0 out of 5 average rating, 49 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
16–21 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
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
4.98 out of 5 average rating, 159 reviews, 1 bed, 1 bathroom
26–31 Jul
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
4.9 out of 5 average rating, 355 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
5.0 out of 5 average rating, 45 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Home in Annapolis
Quaint in the Heart of Annapolis
5.0 out of 5 average rating, 114 reviews, 2 bedrooms, 2 beds, 1 bathroom
24–29 Jul
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
4.96 out of 5 average rating, 223 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Jul
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
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 4 bathrooms
19–24 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
14–19 Aug
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
5.0 out of 5 average rating, 171 reviews, 1 bed, 1 bathroom
16–21 Jul
Top guest favourite
Home in Annapolis
CJ's Cottage
4.96 out of 5 average rating, 73 reviews, 2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Annapolis
Stay Retro Naptown
4.95 out of 5 average rating, 80 reviews, 4 bedrooms, 4 beds, 2 bathrooms
24–29 Jul
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
4.95 out of 5 average rating, 182 reviews, 1 queen bed, 3 bathrooms
26–31 Jul
Top guest favourite
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
4.97 out of 5 average rating, 148 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
18–23 Jul