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Search results; Over 1,000 homes in Gloucester

Guest favourite
Cottage in Gloucester
"Bee Haven" Cottage Retreat
2 bedrooms, 2 beds, 1 private bathroom
30 Aug – 4 Sept
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4.96 out of 5 average rating, 276 reviews
Top guest favourite
Room in Gloucester
Serenity’s Porch Queen, Historic Gloucester VA
1 queen bed, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 60 reviews
Guest favourite
Home in Gloucester
A "Bitt of Home" in the heart of Gloucester.
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.97 out of 5 average rating, 90 reviews
Top guest favourite
Cottage in Gloucester Courthouse
Historic Ware River Cottage at Glebefield
1 bedroom, 3 beds, 1 bathroom
28 Aug – 2 Sept
4.98 out of 5 average rating, 234 reviews
Home in Gloucester
Located in the Heart of Gloucester Courthouse!
3 bedrooms, 3 beds, 2.5 bathrooms
3–8 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Port Haywood
Relax & Heal Cottage Near Ocean & Forest Retreat
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 61 reviews
Flat in Gloucester
Family-Friendly Main St Gloucester Apt w/ Balcony!
2 bedrooms, 4 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 9 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, 110 reviews
Guest favourite
Rooms in Yorktown
Yorktown-3 quaint rooms & bath for 1 group/party.
3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.79 out of 5 average rating, 48 reviews
Resort in Williamsburg
Club Wyndham Governor’s Green Three-Bedroom Suite
3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.66 out of 5 average rating, 80 reviews
Guest favourite
Home in Gloucester
A “Bitt” of Home on Beaver
3 bedrooms, 6 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Loft in Gloucester Courthouse
Marshfield Guesthouse on river near Williamsburg
1 sofa bed, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 356 reviews
Guest favourite
Room in Gloucester
Serenity’s Sand Castle King and Bunk Room
3 beds, 1 bathroom
19–24 Aug
4.97 out of 5 average rating, 31 reviews
Guest favourite
Farm stay in Shacklefords
Blue Heaven in Plainview
4 bedrooms, 6 beds, 2.5 bathrooms
28 Aug – 2 Sept
4.89 out of 5 average rating, 64 reviews
Guest favourite
Home in Gloucester Point
York River Retreat
3 bedrooms, 3 beds, 3 bathrooms
7–12 Sept
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Home in Williamsburg
Williamsburg's Stylish 1959 Mid-Century Modern Gem
4 bedrooms, 7 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Gloucester
The Bee Goode House on Main Street
3 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
4.97 out of 5 average rating, 195 reviews
Guest favourite
Room in Gwynn
Cricket Hill House — Waterfront Suite, 2 East
1 king bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Cottage in Urbanna
Little Dipper -private beach,Kayaks & paddleboards
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 201 reviews