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A steel bridge over a calm river with a sandy beach and rocky outcrops on the right.

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    Check prices for these dates, December 12 – 13, 2026

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    Our top choices for Gloucester cottages

    1. Radiant Gloucester House w/ Private Porch!

    A single-story house with a brick exterior, a covered porch with blue chairs, and a brick pathway leading to the entrance.

    2. Located in the Heart of Gloucester Courthouse!

    A large house with a front porch, surrounded by trees and a gravel driveway.

    3. Restored 1930s Cottage on 1 Acre w/ Fire Pit

    A covered porch with wooden benches and chairs, large windows, and a view of a grassy area.

    4. Restored 1930s Cottage on 1 Acre w/ Fire Pit

    A covered porch with wooden benches and chairs, large windows, and a view of a grassy area.

    5. Bay Dream Believer Cottage on Beautiful East River Waterfront

    A white house with a black front door, a small porch, and a gravel driveway.

    6. Riverfront Cottage: Fire Pit & Kayaks

    A covered outdoor seating area with wicker furniture and red cushions, overlooking a lake and dock.

    7. Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown

    A house with a large lawn, surrounded by tall trees.

    8. Williamsburg Home for Colonial & Theme Park Trips

    A single-story house with a front porch, a small deck, and a driveway leading to the entrance.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Learn more about Gloucester

    Dive into history at the Gloucester Museum before exploring the haunting Rosewell Ruins. Paddle through Beaverdam Park's tranquil waters or ask locals about hidden swimming spots in Middle Peninsula State Park.

    See all hotels in Gloucester

    A steel bridge over a calm river with a sandy beach and rocky outcrops on the right.

    Top reviews in Gloucester

    Warner Hall

    A large white house with a dark roof, multiple chimneys, and a white fence in the foreground.

    Hampton Inn Gloucester

    A Hampton Inn hotel building with a beige facade, large windows, and a clear sky.

    Williamsburg Inn, an official Colonial Williamsburg Hotel

    A large, symmetrical building with a central entrance, surrounded by a reflective pool and well-maintained landscaping.

    Towneplace Suites By Marriott Newport News Airport

    A multi-story hotel with a modern facade, a prominent entrance with a covered area, and a sign indicating it is a Marriott property.

    Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

    A row of two-story houses with brick and white siding, featuring front porches and chimneys.

    Patriots Inn

    A brick building with a sign reading "Patriots Inn" and a flagpole with an American flag.

    Hyatt Select Williamsburg

    Exterior

    Comfort Inn Williamsburg Gateway

    A brick building with a sign reading 'Comfort Inn.'

    Hampton Inn Newport News-Yorktown

    A modern hotel with a covered parking area, a visible entrance, and a sign indicating it is a Hampton Inn.

    Holiday Inn Express Williamsbrg Busch Gardens Area by IHG

    A Holiday Inn Express building with a modern design, featuring a prominent entrance and a parking lot.

    Williamsburg Sampler B & B

    A two-story brick house with a front porch, multiple windows, and a chimney.

    Hampton Inn & Suites Williamsburg-Richmond Rd.

    A Hampton Inn & Suites hotel with a symmetrical facade, multiple windows, and a flagpole with flags.

    Hilton Vacation Club The Historic Powhatan Williamsburg

    A large brick building with a central entrance, surrounded by well-maintained gardens and trees.

    Marriott's Manor Club at Ford's Colony

    A landscaped garden with a symmetrical hedge design, a paved driveway, and a building with multiple windows in the background.

    Sleep Inn Historic Williamsburg

    A Sleep Inn sign with a 220 indoor pool feature.

    Holiday Inn Club Vacations Williamsburg Resort by IHG

    A hotel with a covered entrance, a fountain, and a reflection pool.

    Comfort Suites Williamsburg Historic Area

    A hotel with a prominent 'Comfort Suites' sign, a covered entrance, and a well-lit facade.

    Frequently Asked Questions

    Why book your cottage in Gloucester with Expedia?

    Booking a cottage in Gloucester is as easy as working out your travel dates and choosing an ideal place for outdoor relaxation and recreation. From high-end retreats to inexpensive properties and cottages that offer amenities like laundry facilities, Expedia has something for all traveler styles. As for the best offers around? We've have them as well!

    How can I find cheap cottages in Gloucester?

    With Expedia's filter tool, comparing cheap cottages in Gloucester has never been simpler. To discover stays that'll make your wallet smile, refine your search results by amenities, star rating and budget.

    What is there to do in Gloucester near my cottage?

    The ultimate travel accessory is a well-thought-out travel plan. Gloucester Museum of History is a great place to start your adventures in Gloucester.

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