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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Guest house in Gloucester
Cozy Fall Retreat - Creek Views & Fire Pits
2 bedrooms, 2 beds, 1 private bathroom
15–20 Sept
,
5.0 out of 5 average rating, 202 reviews
Guest favourite
Home in Gloucester
A "Bitt of Home" in the heart of Gloucester.
2 bedrooms, 3 beds
11–16 Sept
4.97 out of 5 average rating, 92 reviews
Home in Gloucester
Located in the Heart of Gloucester Courthouse!
3 bedrooms, 3 beds
10–15 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Cottage in Gloucester
White Heron Cottage
3 bedrooms, 3 beds
27 Sept – 2 Oct
4.91 out of 5 average rating, 264 reviews
Top guest favourite
Flat in Gloucester Courthouse
Right on Main St! Shops, Arts, Dining and More!
1 bedroom, 1 queen bed
9–14 Sept
4.96 out of 5 average rating, 148 reviews
Top guest favourite
Home in Gloucester
Bee Humble Cottage Entire Home
2 bedrooms, 2 king beds
4–9 Nov
4.95 out of 5 average rating, 231 reviews
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, 197 reviews
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
Top guest favourite
Home in Gloucester
A “Bitt” of Home on Beaver
3 bedrooms, 6 beds
10–15 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Room in Gloucester
Serenity’s Porch Queen, Historic Gloucester VA
1 queen bed
9–14 Sept
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Home in Gloucester
Charming Cottage Historic Gloucester Main Street
2 bedrooms, 2 beds
12–17 Sept
4.96 out of 5 average rating, 135 reviews
Top guest favourite
Cottage in Gloucester Courthouse
Historic Ware River Cottage at Glebefield
1 bedroom, 3 beds
18–23 Oct
4.98 out of 5 average rating, 234 reviews
Resort in Williamsburg
Club Wyndham Governor’s Green Three-Bedroom Suite
3 bedrooms, 5 beds
12–17 Sept
4.62 out of 5 average rating, 85 reviews
Guest favourite
Room in Gloucester
Serenity’s Sand Castle King and Bunk Room
3 beds
9–14 Sept
4.97 out of 5 average rating, 31 reviews
Flat in Gloucester
Family-Friendly Main St Gloucester Apt w/ Balcony!
2 bedrooms, 4 beds
9–14 Sept
4.92 out of 5 average rating, 12 reviews
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
Top guest favourite
Home in Gloucester Point
Pointe Haven near Historic Yorktown
3 bedrooms, 3 beds
26 Sept – 1 Oct
4.99 out of 5 average rating, 202 reviews
Top guest favourite
Home in Gloucester
Welcome to this Waterfront Home with Amazing Views
3 bedrooms, 3 beds
27 Oct – 1 Nov
4.98 out of 5 average rating, 113 reviews
Top guest favourite
Home in Williamsburg
Williamsburg’s Stylish 1959 Mid-Century Modern Gem
4 bedrooms, 7 beds
13–18 Sept
5.0 out of 5 average rating, 20 reviews