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

Gloucester Vacation Rentals

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    Check prices for these dates, December 13 – 14, 2026

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    Our top choices for Gloucester vacation rentals

    1. Radiant Gloucester House w/ Private Porch!

    A kitchen with a black and white checkered floor, a brick oven, and modern cabinetry.

    2. Radiant Gloucester House w/ Private Porch!

    A kitchen with a black and white checkered floor, a brick oven, and modern cabinetry.

    3. Located in the Heart of Gloucester Courthouse!

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

    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. Patriots Inn

    A hot tub with a tiled edge and a metal handrail.

    6. The Colonies at Williamsburg

    A swimming pool with a water slide, lounge chairs, and a basketball hoop.

    7. Vacation Village At Williamsburg

    A large building with a swimming pool, multiple lounge chairs, and a covered patio area.

    8. Marriott's Manor Club at Ford's Colony

    A large, multi-story brick building with a central courtyard, surrounded by lush greenery and a golf course.

    9. Bay Dream Believer Cottage on Beautiful East River Waterfront

    A garden pathway leading to a gazebo by a lake, surrounded by trees and shrubs.

    10. 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.

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

    A staircase with a tropical mural on the walls, a wooden handrail, and a fire extinguisher on the landing.

    12. 1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town

    A sandy beach path leading to the ocean, surrounded by dry grass.

    13. Anvil Campground

    A playground with a wooden climbing structure and a green slide.

    14. Quiet Villa with Bowling Alley, Pools, +Mini Golf

    A large historic building with a prominent tower, surrounded by lush gardens and various flowering plants.

    15. Stylish 2BR Suite w/ Balcony | Mini Golf & Pool

    A large historic building with a prominent tower, surrounded by lush gardens and various flowering plants.

    16. Single-Story Townhouse Near Outlets & Attractions

    A living room with a blue accent wall, a flat-screen TV, a modern chandelier, a sofa, a coffee table, and a massage chair.

    17. Log Cabin - Williamsburg Pet-Friendly Log Cabin – Heated Pool, Free Game Room

    Point of interest - Anvil Campground (Williamsburg)

    18. Luxury Riverfront Condo w/ sunrise & sunset views

    A golf course with a water body in the background, surrounded by trees and sand bunkers.

    19. Lovely 2 BR Condo in 4💎 Historic Golf Resort

    A dining area with a round table and six chairs, a sofa, a television, and a fireplace.

    20. Williamsburg Home for Colonial & Theme Park Trips

    A modern kitchen with a central island, bar stools, and a built-in oven.

    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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    Find vacation rentals that suit your style

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    Top Gloucester Hotel Reviews

    Warner Hall

    A large, white, two-story house with a central entrance, a porch, and a symmetrical facade.

    Hornsby House Inn

    A large brick building with a symmetrical facade, multiple chimneys, and a covered porch with steps leading to the entrance.

    Williamsburg Inn, an official Colonial Williamsburg Hotel

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

    Gracefield Hall B&B

    A large, white, two-story house with a steeply pitched roof, surrounded by a well-maintained lawn and tall trees.

    Hampton Inn Gloucester

    A hotel lobby with a reception desk, chairs, a fruit bowl, framed pictures, and a waste bin.

    Vaiden Inn

    An outdoor patio area with string lights, a small table, and a gazebo.

    Towneplace Suites By Marriott Newport News Airport

    A modern kitchen with a refrigerator, microwave, and coffee maker. There is a dining area with a table and chairs, and a small bookshelf.

    A Williamsburg White House

    A white house with a brick pathway leading to the entrance, surrounded by trees and a white picket fence.

    Williamsburg Sampler B & B

    A large planter with pink flowers and a hanging basket with more flowers, placed on a brick wall next to a black door.

    Surry Seafood Company

    A view of a lake with docks, a wooden deck, and a glass of a green beverage with a garnish.

    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 hot tub with a tiled edge and a metal handrail.

    Hampton Inn Newport News-Yorktown

    An indoor swimming pool with clear water, tiled walls, and a wooden floor.

    Cedars of Williamsburg Bed & Breakfast

    A small brick house with a sloped roof, two windows with shutters, and a wooden fence.

    Hyatt Select Williamsburg

    A calm harbor with boats and a lighthouse at sunset.

    Aldrich House Bed & Breakfast

    A spacious living room with a fireplace, a piano, and a large window.

    Comfort Inn Williamsburg Gateway

    A dining area with a long table, multiple chairs, and three hanging crystal chandeliers.

    Find out more about Gloucester

    Everything you need to know about Gloucester vacation rentals

    Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gloucester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

    There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gloucester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Gloucester vacation rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Gloucester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Gloucester in high season.

    Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $33 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

    How to find incredible deals on Gloucester rentals

    At Expedia, we put the best Gloucester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

    To find some top Gloucester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gloucester vacation.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gloucester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

    Frequently Asked Questions

    Can I find a vacation rental in Gloucester?

    Yes, we give you a choice of vacation rentals where you'll be only 13.8 mi (22.2 km) from Busch Gardens Williamsburg, offering you a more remote option if you want a quieter place to stay. Gloucester is known for its festivals and art.

    What are some of the best vacation rentals in Gloucester?

    Perfect for long-term workers & short stays—comfort, style & convenience await!: This Gloucester vacation home rental is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Another good choice for your trip to Gloucester is Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock.

    How many vacation rentals are there in Gloucester?

    Expedia has 17 vacation rentals for your stay in Gloucester.

    What’s there to see and do in Gloucester?

    Brown Park and Ark Park are a couple of scenic spots to enjoy the outdoors, whereas Gloucester Museum of History is one of the cultural attractions. Other places in town to visit include Main Street Center and Gloucester Public Library.

    What’s a vacation rental in Gloucester like?

    Vacation rentals are privately owned properties where you can stay for a couple of days or more in Gloucester. Vacation rentals provide amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.

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