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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
Studio, 2 beds, 1 private bathroom
4–9 Oct
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4.97 out of 5 average rating, 100 reviews
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Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed, 1 bathroom
1–6 Oct
4.95 out of 5 average rating, 138 reviews
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Home in Annapolis
The 1845 Outpost
3 bedrooms, 3 king beds, 2 bathrooms
1–6 Oct
New place to stay
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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, 191 reviews
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Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds, 4 bathrooms
1–6 Oct
New place to stay
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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
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.9 out of 5 average rating, 52 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, 260 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
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Oct
4.94 out of 5 average rating, 83 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
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 23 reviews
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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, 20 reviews
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Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms, 4 beds, 1.5 bathrooms
1–6 Oct
4.98 out of 5 average rating, 55 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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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Oct
New place to stay
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Flat in Annapolis
Annapolis Getaway | 2BR Sleeps 6 | Near USNA
3 bedrooms, 2 beds, 2 bathrooms
1–6 Oct
New place to stay
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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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Home in Edgewater
Water's edge retreat ready to relax with you
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Nov
New place to stay