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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest house in Annapolis
Garden View, a spacious 1 bedroom with loft.
2 bedrooms, 3 beds, 1 private bathroom
30 Jul – 4 Aug
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4.99 out of 5 average rating, 161 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
16–21 Jul
4.92 out of 5 average rating, 72 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
26–31 Jul
4.95 out of 5 average rating, 180 reviews
Top guest favourite
Room in Annapolis
Lovely Private Master Bedroom
1 queen bed
5–10 Jul
4.98 out of 5 average rating, 246 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
9–14 Jul
4.99 out of 5 average rating, 154 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
19–24 Jul
4.98 out of 5 average rating, 58 reviews
Guest favourite
Home in Annapolis
1 Block to USNA Stadium: Modern Annapolis Home!
2 bedrooms, 3 beds
12–17 Jul
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
22–27 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
10–15 Aug
4.92 out of 5 average rating, 1121 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
19–24 Jul
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
16–21 Aug
4.97 out of 5 average rating, 93 reviews
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed
7–12 Sept
4.99 out of 5 average rating, 349 reviews
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
1 bedroom, 2 beds
10–15 Jul
5.0 out of 5 average rating, 90 reviews
Top guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds
24–29 Jul
4.95 out of 5 average rating, 79 reviews
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds
5–10 Jul
4.96 out of 5 average rating, 256 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
1 bedroom, 1 bed
12–17 Jul
4.9 out of 5 average rating, 103 reviews
Top guest favourite
Flat in Annapolis
Upscale Condo In Annapolis w/Private Parking
2 bedrooms, 3 beds
5–10 Jul
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed
6–11 Jul
4.96 out of 5 average rating, 127 reviews
Superhost
Flat in Annapolis
Charming Eastport
1 bedroom, 1 queen bed
5–10 Jul
4.77 out of 5 average rating, 296 reviews