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Search results; Over 1,000 homes in Annapolis

Guest favourite
Apartment in Annapolis
Capts Qrtrs - Awesome downtown Annapolis location!
1 bedroom, 1 bed, 1 private bathroom
9–14 Aug
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4.86 out of 5 average rating, 184 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
30 Jul – 4 Aug
4.92 out of 5 average rating, 78 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds, 1 bathroom
11–16 Aug
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds, 1 bathroom
26–31 Jul
4.91 out of 5 average rating, 137 reviews
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
1 bedroom, 2 beds, 1.5 bathrooms
21–26 Jul
5.0 out of 5 average rating, 93 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
26–31 Jul
4.98 out of 5 average rating, 159 reviews
Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Annapolis
Quaint in the Heart of Annapolis
2 bedrooms, 2 double beds, 1 bathroom
24–29 Jul
5.0 out of 5 average rating, 114 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed, 1 bathroom
16–21 Jul
4.96 out of 5 average rating, 223 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 355 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
10–15 Aug
4.89 out of 5 average rating, 361 reviews
Home in Pasadena
Spacious Family Home in Pasadena
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Jul
New place to stay
Guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
1 bed, 1 bathroom
16–21 Jul
5.0 out of 5 average rating, 171 reviews
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms, 4 beds, 4 bathrooms
19–24 Jul
5.0 out of 5 average rating, 16 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
1–6 Aug
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds, 2 bathrooms
24–29 Jul
4.95 out of 5 average rating, 80 reviews
Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms, 4 beds, 1.5 bathrooms
16–21 Jul
5.0 out of 5 average rating, 49 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
26–31 Jul
4.95 out of 5 average rating, 182 reviews