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Search results; Over 1,000 homes in Annapolis

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Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 bed, 1 private bathroom
26–31 Oct
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4.95 out of 5 average rating, 212 reviews
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Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
8–13 Nov
4.94 out of 5 average rating, 192 reviews
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Flat in Annapolis
Annapolis Getaway | 2BR Sleeps 6 | Near USNA
3 bedrooms, 2 beds, 2 bathrooms
4–9 Oct
New place to stay
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Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds, 2 bathrooms
31 Oct – 5 Nov
4.97 out of 5 average rating, 261 reviews
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Guest favourite
Home in Annapolis
Across from stadium - walk to downtown Annapolis!
4 bedrooms, 4 beds, 3 bathrooms
4–9 Oct
4.9 out of 5 average rating, 136 reviews
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Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.91 out of 5 average rating, 53 reviews
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Top guest favourite
Cottage in Annapolis
Charming Cottage 2 parking spot easy walk downtown
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.94 out of 5 average rating, 215 reviews
Photo 1 of 29
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
4–9 Dec
4.96 out of 5 average rating, 268 reviews
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Top guest favourite
Home in Annapolis
Quiet Waterfront
3 bedrooms, 3 beds, 3 bathrooms
6–11 Dec
4.98 out of 5 average rating, 191 reviews
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Guest favourite
Flat in Annapolis
Charming Navy-Themed Townhome | Walk to USNA & DTA
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.93 out of 5 average rating, 118 reviews
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Top guest favourite
Room in Annapolis
A Cottage Room in Presidents Hill
1 single bed, 1.5 bathrooms
4–9 Oct
4.89 out of 5 average rating, 186 reviews
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Top guest favourite
Room in Annapolis
Guest Suite Getaway near Naval Academy Stadium
1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 175 reviews
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Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed, 1 bathroom
18–23 Oct
4.9 out of 5 average rating, 368 reviews
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Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
11–16 Oct
4.98 out of 5 average rating, 168 reviews
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Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Home in Annapolis
4BR Walk to USNA & Dock · Parking
4 bedrooms, 4 beds, 4 bathrooms
1–6 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
4.96 out of 5 average rating, 230 reviews