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

Brattleboro Vacation Rentals

Q: What's the top vacation rental in Brattleboro?

The Jelly Mill-A Peaceful River Retreat : This highly rated vacation home rental in Brattleboro 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 fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

Dates

November 2026

December 2026

Check prices for these dates

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Our top choices for Brattleboro vacation rentals

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

1. Cozy Vermont Tiny Home Get Away

Brattleboro

Anthony L.

$85 nightly

Nov 30 - Dec 1

Total with taxes and fees

A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

2. Vikings Villages Resort - Double Bed Room

Guilford

$311 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

3. Stunning Glass House nestled in the Vermont wilderness!

Guilford

Chris O.

$352 nightly

Nov 18 - Nov 19

Total with taxes and fees

A wooden interior with a kitchen, bar area, and dining space.

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

Brattleboro

James M.

$207 nightly

Nov 18 - Nov 19

Total with taxes and fees

A yurt interior with a bed, wooden lattice walls, and a door leading to an outdoor balcony.

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

Hinsdale

Adrienne

$145 nightly

Nov 11 - Nov 12

Total with taxes and fees

A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

6. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Wilmington

Mark

A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

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

Newfane

Joseph P.

$241 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

8. Family Friendly Hilltop House In Putney Vermont

Putney

Susan G.

$233 nightly

Nov 11 - Nov 12

Total with taxes and fees

9. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Wilmington

Rod M.

A wooden house with a porch lit by string lights, surrounded by snow.

10. Chalet Mount Snow/Stratton Skiing/hiking

East Dover

Chelsea G.

$331 nightly

Nov 8 - Nov 9

Total with taxes and fees

A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

11. Lovely 2nd Floor Apartment

Greenfield

heather

$207 nightly

Nov 8 - Nov 9

Total with taxes and fees

A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

12. Long Trail House at Stratton Mountain Resort

Stratton

Michael

$391 nightly

Nov 8 - Nov 9

Total with taxes and fees

13. 3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails

Halifax

Justin M.

$422 nightly

Nov 9 - Nov 10

Total with taxes and fees

A cozy living room with a fireplace, leather sofas, and a television mounted on the wall.

14. Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Whitingham

Ben B.

$532 nightly

Nov 8 - Nov 9

Total with taxes and fees

A room with a wood-burning stove, a brick fireplace, a mounted television, and a sign above the fireplace.

15. Cozy 3 bedroom condo 2.5 miles to Mount Snow

West Dover

Scott S.

$241 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

16. The Eagles Wing at The CHM - Private Apartment

Dover

Ava M.

$109 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

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

Greenfield

JAMES S.

$198 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

18. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Dover

Tania J.

$260 nightly

Nov 8 - Nov 9

Total with taxes and fees

A house with a staircase leading to a porch, surrounded by snow and string lights.

19. Light-filled treetop apartment close to downtown Greenfield and Highland Park

Greenfield

Tom

$123 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern kitchen with a wooden countertop, dark cabinets, and a large window.

20. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Keene

cody s.

$321 nightly

Nov 9 - Nov 10

Total with taxes and fees

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Find vacation rentals that suit your style

Top Brattleboro Hotel Reviews

A wooden cabin with a thatched roof, accessible via a wooden walkway with railings.

Vikings Villages Resort

Guilford

10/10 Excellent

Diego

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

Inn At Mount Snow

West Dover

10/10 Excellent

Peter

A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

Inn on Putney Road

Brattleboro

10/10 Excellent

Victoria

A dock extending into a lake with a grassy area in the foreground and trees in the background.

Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

10/10 Excellent

James

A room with two single beds, a desk, and a radiator.

Colonel Williams Inn

Brattleboro

10/10 Excellent

Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...

Ann

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

Four Columns Inn

Newfane

10/10 Excellent

Nettie

A two-story house with a porch and a covered area, surrounded by trees and a driveway.

The Wilmington Inn

Wilmington

10/10 Excellent

Sophia

A two-story house with a red door, green shutters, and a snow-covered front yard.

Centennial House

Northfield

10/10 Excellent

My husband and I have never stayed at a B&B. We were looking for a nearby weekend get-away and found The Centennial House on an on-line search. The Hosts Joan & Steve were very hospitable and knowledgable of the area and it's history and attractions. The surrounding area, the room and the breakfast were beautiful, comfortable and delicious!! Our first B&B experience was excellent, thank you Joan & Steve. Until we meet again, Bill & Anne

Anonymous traveler

A modern outdoor lounge area with two lounge chairs and a wooden deck.

Otherland Hotel

Newfane

10/10 Excellent

The property is very well maintained and decorated. The room and bathroom are very clean. It has two very nice common area with 2 big windows that made them bright and sunny and cozy. It's also along a major highway so it's easy to find. The owners/operators of this hotel are very kind, thoughtful and accomodating to the needs of their guests. I especially and directly experienced their wonderful hospitality as a disabled person in a wheelchair. When I inquired about the accessibility of...

Rosalie

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

Harvest Barn Inn

Bellows Falls

10/10 Excellent

Virginia

A dining area with wooden tables and chairs, large windows with a view of trees, and a bench along the wall.

The Carriage Barn Inn

Keene

10/10 Excellent

Richard

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

The Inn At Crumpin Fox

Bernardston

10/10 Excellent

I've traveled quite frequently the past several years and I can say in all honesty that this is without doubt one of the nicest places I have stayed. I was there for 2 nights and could not have asked for nicer accomodations. The room was spacious, the bed very comfortable and the bathroom spotless. The manager was very gracious, he even lent me his umbrella when it rained the day I had planned to do genealogy research in a local cemetery.

Anonymous traveler

A large, two-story house with a snow-covered driveway and surrounding trees.

Chesterfield Inn

West Chesterfield

10/10 Excellent

Our stay at the Chesterfield Inn was absolutely wonderful. The inn is sweet, charming, and full of character. We slept so good and our room was so peaceful. We were treated to a beautiful sunset, enjoyed a delicious breakfast next morning, and appreciated the warm hospitality throughout our stay. The staff was exceptionally kind, welcoming, and helpful, making us feel right at home. We would definitely stay here again and highly recommend it to anyone looking for a relaxing New England getaway.

Beverly

A stone fire pit with flames in front of a house with a covered porch and blue lighting.

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

10/10 Excellent

Anthony

Find out more about Brattleboro

Everything you need to know about Brattleboro 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 Brattleboro 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 Brattleboro vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Brattleboro vacation 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 low season months. For more hustle and bustle, you may prefer to visit Brattleboro 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 $95 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 Brattleboro rentals

At Expedia, we put the best Brattleboro 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 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 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 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 vacation rentals in Brattleboro?

Yes, we offer vacation rentals in Brattleboro near New England Center for Circus Arts, or you can select a secluded option if you're looking for extra privacy while you relax. 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's the top vacation rental in Brattleboro?

The Jelly Mill-A Peaceful River Retreat: This highly rated vacation home rental in Brattleboro 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 fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Brattleboro?

Expedia has 30 vacation 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 vacation rental in Brattleboro like?

Vacation rentals are private properties where you can stay for a long or short time in Brattleboro. Vacation rentals provide amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for families.

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Things to do in Brattleboro
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