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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Home in Gloucester
Charming Waterfront Home on Piankatank River!
3 bedrooms, 4 beds, 2 private bathrooms
14–19 Sept
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4.98 out of 5 average rating, 123 reviews
Guest favourite
Home in Gloucester
A "Bitt of Home" in the heart of Gloucester.
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.97 out of 5 average rating, 92 reviews
Top guest favourite
Cottage in North
The Nook; Peaceful 2 bedroom cottage by the bay
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 182 reviews
Guest favourite
Home in Gloucester
Spring is a great time in Gloucester!
3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 94 reviews
Top guest favourite
Home in Gloucester
Severnly Pointe Cottage Waterfront Retreat
4 bedrooms, 6 beds, 2 bathrooms
21–26 Sept
4.9 out of 5 average rating, 114 reviews
Top guest favourite
Flat in Gloucester Courthouse
Right on Main St! Shops, Arts, Dining and More!
1 bedroom, 1 queen bed, 1 bathroom
1–6 Nov
4.96 out of 5 average rating, 148 reviews
Top guest favourite
Home in Gloucester
A “Bitt” of Home on Beaver
3 bedrooms, 6 beds, 2 bathrooms
23–28 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Gloucester Point
Pointe Haven near Historic Yorktown
3 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
4.99 out of 5 average rating, 203 reviews
Top guest favourite
Home in Gloucester
Bee Humble Cottage Entire Home
2 bedrooms, 2 king beds, 1 bathroom
8–13 Nov
4.95 out of 5 average rating, 231 reviews
Home in Gloucester
Located in the Heart of Gloucester Courthouse!
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Gloucester
Waterfront Golden River Watch
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.9 out of 5 average rating, 124 reviews
Guest favourite
Cottage in Gloucester
White Heron Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.91 out of 5 average rating, 265 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, 198 reviews
Guest favourite
Room in Gloucester
Serenity’s "Dream On" Suite, Historic Virginia
1 double bed, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Guest suite in Gloucester
Carriage House
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Gloucester
Squeaky Shores on the York River
5 bedrooms, 7 beds, 4 bathrooms
14–19 Sept
4.79 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Gloucester
Eclectic and Cozy Apartment
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 70 reviews
Guest favourite
Farm stay in Shacklefords
Blue Heaven in Plainview
4 bedrooms, 6 beds, 2.5 bathrooms
20–25 Sept
4.89 out of 5 average rating, 66 reviews
Top guest favourite
Cottage in Cobbs Creek
Waterfront w/Floating Dock, Kayaks~Family Home
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 105 reviews