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Search results; Over 1,000 homes in Annapolis

Guest favourite
Apartment in Annapolis
Renovated Apt In Historic Dist w/2 Parking Spots
2 bedrooms, 3 beds, 1 private bathroom
9–14 Aug
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4.94 out of 5 average rating, 444 reviews
Home in Pasadena
Spacious Family Home in Pasadena
New place to stay, 3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
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
Top guest favourite
Guest house in Annapolis
"The Perch" - Hot Tub - Beach - Chesapeake Bay
4.91 out of 5 average rating, 95 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 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
19–24 Jul
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
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
Bay View Studio Apartment
4.97 out of 5 average rating, 94 reviews, 2 beds, 1 bathroom
16–21 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
26–31 Jul
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
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 6 beds, 2 bathrooms
24–29 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
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
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
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
5.0 out of 5 average rating, 93 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
26–31 Jul