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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
22–27 Sept
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5.0 out of 5 average rating, 205 reviews
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Guest favourite
Home in Gloucester
A "Bitt of Home" in the heart of Gloucester.
2 bedrooms, 3 beds
18–23 Sept
4.97 out of 5 average rating, 92 reviews
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Guest favourite
Cottage in Gloucester
White Heron Cottage
3 bedrooms, 3 beds
27 Sept – 2 Oct
4.91 out of 5 average rating, 266 reviews
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Home in Gloucester
Located in the Heart of Gloucester Courthouse!
3 bedrooms, 3 beds
7–12 Nov
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Gloucester
The Bee Goode House on Main Street
3 bedrooms, 3 beds
28 Sept – 3 Oct
4.97 out of 5 average rating, 198 reviews
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Top guest favourite
Home in Gloucester
Bee Humble Cottage Entire Home
2 bedrooms, 2 king beds
8–13 Nov
4.95 out of 5 average rating, 231 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
18–23 Sept
4.96 out of 5 average rating, 149 reviews
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Guest favourite
Home in Gloucester
Serenity Farm Equestrian Retreat in Historic VA
5 bedrooms, 7 beds
21–26 Sept
5.0 out of 5 average rating, 29 reviews
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Guest favourite
Room in Gloucester
Serenity’s "Dream On" Suite, Historic Virginia
1 double bed
17–22 Sept
4.97 out of 5 average rating, 29 reviews
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Top guest favourite
Home in Gloucester
Charming Cottage Historic Gloucester Main Street
2 bedrooms, 2 beds
20–25 Sept
4.96 out of 5 average rating, 135 reviews
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Top guest favourite
Home in Gloucester
A “Bitt” of Home on Beaver
3 bedrooms, 6 beds
23–28 Sept
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Cottage in Gloucester Courthouse
Historic Ware River Cottage at Glebefield
1 bedroom, 3 beds
9–14 Oct
4.98 out of 5 average rating, 234 reviews
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Top guest favourite
Home in Gloucester
Grey Heron Haven
3 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 170 reviews
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Guest favourite
Room in Gloucester
Serenity’s Sand Castle King and Bunk Room
3 beds
17–22 Sept
4.97 out of 5 average rating, 31 reviews
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Resort in Williamsburg
Club Wyndham Governor’s Green Three-Bedroom Suite
3 bedrooms, 5 beds
20–25 Sept
4.64 out of 5 average rating, 89 reviews
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Top guest favourite
Farm stay in Gloucester
Historic Farmhouse. Peace & Quiet on 5 acres
3 bedrooms, 7 beds
18–23 Sept
4.93 out of 5 average rating, 135 reviews
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Guest favourite
Home in Port Haywood
Relax & Heal Cottage Near Ocean & Forest Retreat
2 bedrooms, 3 beds
12–17 Oct
4.94 out of 5 average rating, 69 reviews
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Home in Gloucester
Radiant Gloucester House w/ Private Porch!
2 bedrooms, 4 beds
30 Sept – 5 Oct
4.85 out of 5 average rating, 75 reviews
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Guest favourite
Farm stay in Shacklefords
Blue Heaven in Plainview
4 bedrooms, 6 beds
20–25 Sept
4.89 out of 5 average rating, 66 reviews