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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
Studio, 1 bed, 1 private bathroom
26–31 Jul
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4.98 out of 5 average rating, 160 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
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
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 183 reviews, 1 queen bed, 1.5 bathrooms
10–15 Aug
Top guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
4.96 out of 5 average rating, 72 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Jul
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
4.89 out of 5 average rating, 362 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 30 reviews, 3 bedrooms, 2 bathrooms
19–24 Jul
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
4.97 out of 5 average rating, 94 reviews, 2 beds, 1 bathroom
16–21 Aug
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
16–21 Aug
Top guest favourite
Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
5.0 out of 5 average rating, 54 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
10–15 Aug
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 180 reviews, 1 queen bed, 1.5 bathrooms
16–21 Aug
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
19–24 Jul
Top guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
4.96 out of 5 average rating, 130 reviews, 1 queen bed, 1 bathroom
21–26 Jul
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
4.93 out of 5 average rating, 58 reviews, 1 bedroom, 2 beds, WC
25–30 Jul
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
5.0 out of 5 average rating, 172 reviews, 1 bed, 1 bathroom
19–24 Jul
Hotel room in Annapolis
Governor Calvert King | Historic Inns
4.59 out of 5 average rating, 34 reviews, 1 bedroom, 1 bathroom
1–6 Aug
Superhost
Flat in Annapolis
Modern Eastport Getaway, Near Historic Annapolis
4.84 out of 5 average rating, 19 reviews, 1 bedroom, 3 beds, 1 bathroom
19–24 Jul
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
4.93 out of 5 average rating, 30 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
26–31 Jul