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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Waterfront farm retreat for vacation & telework
3 bedrooms, 5 beds, 1.5 shared bathrooms
1–6 Nov
,
4.98 out of 5 average rating, 161 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
4.92 out of 5 average rating, 24 reviews, 2 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Home in Annapolis
CJ's Cottage
4.96 out of 5 average rating, 75 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
4.97 out of 5 average rating, 96 reviews, 2 beds, 1 bathroom
14–19 Aug
Guest favourite
Home in Arnold
Rachel's BnB
4.91 out of 5 average rating, 139 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Room in Annapolis
Lovely Private Master Bedroom
4.98 out of 5 average rating, 247 reviews, 1 queen bed, 1 bathroom
1–6 Aug
Top guest favourite
Flat in Annapolis
Serene Hideaway
5.0 out of 5 average rating, 30 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
4.96 out of 5 average rating, 224 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.93 out of 5 average rating, 82 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
23–28 Aug
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
4.96 out of 5 average rating, 131 reviews, 1 queen bed, 1 bathroom
2–7 Aug
Top guest favourite
Boat in Annapolis
Welcome Aboard!
4.96 out of 5 average rating, 112 reviews, 2 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
4.98 out of 5 average rating, 161 reviews, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 16 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
4.94 out of 5 average rating, 31 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
10–15 Aug
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 181 reviews, 1 queen bed, 1.5 bathrooms
16–21 Aug
Top guest favourite
Guest house in Annapolis
"The Perch" - Hot Tub - Beach - Chesapeake Bay
4.91 out of 5 average rating, 96 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
4.93 out of 5 average rating, 58 reviews, 1 bedroom, 2 beds, WC
1–6 Aug
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.94 out of 5 average rating, 31 reviews, 3 bedrooms, 2 bathrooms
10–15 Aug
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
4.98 out of 5 average rating, 62 reviews, 2 bedrooms, 1.5 bathrooms
24–29 Aug