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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
Severnly Pointe Cottage Waterfront Retreat
4 bedrooms, 6 beds, 2 private bathrooms
15–20 Sept
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4.9 out of 5 average rating, 114 reviews
Guest favourite
Home in Gloucester
A "Bitt of Home" in the heart of Gloucester.
2 bedrooms, 3 beds, 1 bathroom
11–16 Sept
4.97 out of 5 average rating, 92 reviews
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
Guest favourite
Cottage in Gloucester
White Heron Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
4.91 out of 5 average rating, 264 reviews
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
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
Guest favourite
Home in Gloucester
The Bee Goode House on Main Street
3 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.97 out of 5 average rating, 197 reviews
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
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
Top guest favourite
Cottage in Gloucester Courthouse
Historic Ware River Cottage at Glebefield
1 bedroom, 3 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 234 reviews
Guest favourite
Home in Gloucester
Charming Cottage Historic Gloucester Main Street
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
4.95 out of 5 average rating, 133 reviews
Top guest favourite
Home in Gloucester
Grey Heron Haven
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 168 reviews
Resort in Williamsburg
Club Wyndham Governor’s Green Three-Bedroom Suite
3 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
4.62 out of 5 average rating, 84 reviews
Top guest favourite
Home in Port Haywood
Relax & Heal Cottage Near Ocean & Forest Retreat
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 65 reviews
Top guest favourite
Home in Gloucester
Welcome to this Waterfront Home with Amazing Views
3 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 112 reviews
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
Top guest favourite
Guest suite in Gloucester
Carriage House
1 bedroom, 2 beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 25 reviews
Flat in Gloucester
Family-Friendly Main St Gloucester Apt w/ Balcony!
2 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.91 out of 5 average rating, 11 reviews
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