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A river with a bridge, a town, and surrounding hills.

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    Check prices for these dates, 13 – 14 December 2026

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    Our top choices for Brattleboro holiday rentals

    1. Cozy Vermont Tiny Home Get Away

    A compact kitchen with wooden cabinets, a built-in microwave, and a refrigerator.

    2. Stunning Glass House nestled in the Vermont wilderness!

    A modern interior with large windows, a wooden ceiling, and a cozy seating area.

    3. The Studio with a View. Bring your dog, too!

    A cozy cabin interior with a wooden interior, a sofa, a dining table with bar stools, and a kitchen area.

    4. Vikings Villages Resort - Double Bed Room

    A rustic log cabin with a steeply pitched roof, a prominent door with a decorative cross, and a small porch with two Adirondack chairs.

    5. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

    A wooden deck with a rustic outdoor seating area, including Adirondack chairs and a small table, surrounded by a forested area with a wooden structure in the background.

    6. Wellness Getaway with a Personal Sauna, and Private River Beach!

    A wooden staircase leading up to a wooden bridge in a forested area.

    7. The Eagles Wing at The CHM - Private Apartment

    A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

    8. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

    A blue house with a porch, a wooden bench, and a door.

    9. Chalet Mount Snow/Stratton Skiing/hiking

    A deck with a fire pit, chairs, and a table.

    10. Family Friendly Hilltop House In Putney Vermont

    A garden with a wooden pergola, purple flowers, and a river view.

    11. 2 Twin beds on 1st floor with En-suite bathroom.

    A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

    12. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

    A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

    13. Cozy 3 bedroom condo 2.5 miles to Mount Snow

    A calm lake with a wooden boat on the shore.

    14. Seasons ski-in/ski-out condo with balcony and wood-burning fireplace

    A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

    15. Lovely 2nd Floor Apartment

    A wooden door with a mirror, a small basket with dried flowers, and a light switch on the wall.

    16. Yurt Oasis in the woods of Hinsdale, NH

    A wooden deck with a grill and propane tank, surrounded by trees.

    17. Private room with En-suite bathroom Marigold Room

    A dining room with a wooden table, chairs, a fireplace, a bookcase, and a stained glass ceiling light.

    18. Cozy Cedar Cabin 8 Min to Mount Snow

    A wooden deck with outdoor furniture and string lights.

    19. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

    A rural landscape with a house surrounded by autumn foliage and a river.

    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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    Top Brattleboro Hotel Reviews

    Inn At Mount Snow

    A modern living room with a fireplace, large windows, and a cozy seating area.

    Colonel Williams Inn

    A bedroom with a large bed, a fireplace, and a window with a view of trees.

    Four Columns Inn

    A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

    Centennial House

    A sign for the Centennial House, indicating it is a bed and breakfast with a historical theme, established in 1811.

    Harvest Barn Inn

    A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

    Otherland Hotel

    A wooden bench by a river with a forest backdrop.

    Blue Vista Motor Lodge

    A fire pit with four Adirondack chairs arranged around it, overlooking a snowy landscape with distant mountains.

    The Burrell House

    A historic brick building with a porch and a sign reading "Burrell House."

    The Carriage Barn Inn

    A wooden table set with plates, cutlery, and a folded napkin.

    The Inn At Crumpin Fox

    A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.

    Find out more about Brattleboro

    Everything you need to know about Brattleboro holiday rentals

    Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Brattleboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Brattleboro holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Brattleboro holiday rentals: An excellent choice for every season

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

    Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Brattleboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Brattleboro holiday rentals we have selected for you start as low as £73 per night. Entering your travel dates in the search wizard you might find even better deals!

    How to find incredible deals on Brattleboro rentals

    At Expedia, we put the best Brattleboro holiday 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 Brattleboro 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 Brattleboro holiday.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Brattleboro. 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

    Are there holiday rentals in Brattleboro?

    Yes, there are holiday rentals in Brattleboro close to New England Center for Circus Arts, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and ski slopes in Brattleboro. Leave some time to check out the shops and entertainment venues during your trip.

    What are some of the best holiday rentals that Brattleboro has to offer?

    The Jelly Mill-A Peaceful River Retreat: This highly rated holiday home rental in Brattleboro is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

    How many holiday rentals are there in Brattleboro?

    Expedia has 30 holiday rentals for your stay in Brattleboro.

    What can I see and do in Brattleboro?

    Enjoy the outdoors at Brattleboro Common and Hogback Mountain Conservation Area, or simply take in cultural attractions like The Stone Church and Hooker-Dunham Theater & Gallery. Other places in town to visit include Latchis Theatre and Vermont Marketplace.

    What’s a holiday rental in Brattleboro like?

    Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Brattleboro. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips.