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Search results; Over 1,000 homes in Gloucester

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Top guest favourite
Guest house in Gloucester
Cozy Fall Retreat - Creek Views & Fire Pits
2 bedrooms, 2 beds, 1 private bathroom
15–20 Sept
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5.0 out of 5 average rating, 200 reviews
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Guest favourite
Home in Gloucester
A "Bitt of Home" in the heart of Gloucester.
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.97 out of 5 average rating, 91 reviews
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Top guest favourite
Room in Gloucester
Serenity’s Porch Queen, Historic Gloucester VA
1 queen bed, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 61 reviews
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Top guest favourite
Flat in Gloucester Courthouse
Right on Main St! Shops, Arts, Dining and More!
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.96 out of 5 average rating, 147 reviews
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Top guest favourite
Home in Gloucester
A “Bitt” of Home on Beaver
3 bedrooms, 6 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Cottage in North
The Nook; Peaceful 2 bedroom cottage by the bay
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 179 reviews
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Superhost
Home in Gloucester
The Bee Goode House on Main Street
3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
4.97 out of 5 average rating, 197 reviews
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Guest favourite
Home in Gloucester
Serenity Farm Equestrian Retreat in Historic VA
5 bedrooms, 7 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 29 reviews
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Guest favourite
Cottage in Gloucester
White Heron Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
14–19 Sept
4.91 out of 5 average rating, 263 reviews
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Top guest favourite
Tiny home in North
The Callie Cottage at Belmont
1 bedroom, 1 double bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Gloucester
Bee Humble Cottage Entire Home
2 bedrooms, 2 king beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 231 reviews
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Home in Gloucester
Squeaky Shores on the York River
5 bedrooms, 7 beds, 4 bathrooms
7–12 Sept
4.77 out of 5 average rating, 22 reviews
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Top guest favourite
Home in Gloucester
Charming Waterfront Home on Piankatank River!
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.98 out of 5 average rating, 123 reviews
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Top guest favourite
Farm stay in Gloucester
Historic Farmhouse. Peace & Quiet on 5 acres
3 bedrooms, 7 beds, 2.5 bathrooms
14–19 Sept
4.92 out of 5 average rating, 133 reviews
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Guest favourite
Home in Gloucester
Spring is a great time in Gloucester!
3 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.97 out of 5 average rating, 92 reviews
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Home in Gloucester
Located in the Heart of Gloucester Courthouse!
3 bedrooms, 3 beds, 2.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 4 reviews
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Superhost
Farm stay in Shacklefords
Blue Heaven in Plainview
4 bedrooms, 6 beds, 2.5 bathrooms
7–12 Sept
4.89 out of 5 average rating, 64 reviews
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Top guest favourite
Loft in Gloucester Courthouse
Marshfield Guesthouse on river near Williamsburg
1 sofa bed, 1 bathroom
14–19 Sept
4.98 out of 5 average rating, 357 reviews
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Home in Gloucester
Waterfront Golden River Watch
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.9 out of 5 average rating, 122 reviews