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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 private bathroom
17–22 Oct
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5.0 out of 5 average rating, 226 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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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
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
Home in Annapolis
Walk to Navy Stadium & Shops. No cleaning fee!
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 37 reviews
Photo 1 of 29
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
25–30 Oct
4.97 out of 5 average rating, 68 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 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
Home in Annapolis
Downtown Annapolis House Rental
5 bedrooms, 5 beds, 4 bathrooms
1–6 Oct
4.95 out of 5 average rating, 19 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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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
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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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Oct
New place to stay
Photo 1 of 29
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
Photo 1 of 29
Top guest favourite
Home in Annapolis
Annapolis waterfront, private pier with kayaks
4 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 46 reviews
Photo 1 of 29
Top guest favourite
Guest house in Annapolis
Garden View, 1 Bedroom and a Loft.
2 bedrooms, 3 beds, 1 bathroom
17–22 Oct
4.99 out of 5 average rating, 167 reviews
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Home in Annapolis
Beautiful 6BR home in Annapolis
6 bedrooms, 6 beds, 4 bathrooms
4–9 Oct
4.63 out of 5 average rating, 71 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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Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds, 2 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 43 reviews