Brattleboro Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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

Cozy Vermont Tiny Home Get Away
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"super cute tiny house! my partner and I had a wonderful time here. It's super close to downtown Brattleboro in a beautiful neighborhood"
United States
Anthony L.
The price is CA $102
CA $134 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Vermont Tiny Home Get Away
A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

2. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is CA $385
CA $449 total
includes taxes & fees
Nov 8 - Nov 9
Vikings Villages Resort - Double Bed Room
A hot tub with a wooden exterior, a mesh chair, and a small step stool on a wooden deck.

3. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.4 out of 10, Exceptional, (3 reviews)
"The glass part of the house is stunning! We wanted to spend all of our time there, and wished that we could enjoy the view from the kitchen and bedroom too. We opted to sleep on the fold-out bed in the glass room instead of in the below-ground bedroom. It was a nice experience!"
United States
Chris O.
The price is CA $212
CA $558 total
includes taxes & fees
Nov 18 - Nov 19
Stunning Glass House nestled in the Vermont wilderness!
A wooden interior with a kitchen, bar area, and dining space.

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

The Studio with a View. Bring your dog, too!
Brattleboro
9.8 out of 10, Exceptional, (8 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is CA $163
CA $335 total
includes taxes & fees
Nov 18 - Nov 19
The Studio with a View. Bring your dog, too!
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

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (21 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is CA $145
CA $229 total
includes taxes & fees
Nov 9 - Nov 10
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

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

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
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!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is CA $231
CA $392 total
includes taxes & fees
Nov 17 - Nov 18
Wellness Getaway with a Personal Sauna, and Private River Beach!
A garden with a wooden pergola, purple flowers, and a river view.

8. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (65 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is CA $207
CA $379 total
includes taxes & fees
Nov 9 - Nov 10
Family Friendly Hilltop House In Putney Vermont
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

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

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (49 reviews)
"Great property and location. Communications with host excellent. Love the privacy and availability of firewood."
United States
Rod M.
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A wooden house with a porch lit by string lights, surrounded by snow.

10. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (17 reviews)
"Clean, cozy, set back and had all the amenities that you would need"
United States
Chelsea G.
The price is CA $123
CA $533 total
includes taxes & fees
Nov 8 - Nov 9
Chalet Mount Snow/Stratton Skiing/hiking
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

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (73 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is CA $214
CA $332 total
includes taxes & fees
Nov 8 - Nov 9
Lovely 2nd Floor Apartment
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

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (85 reviews)
"Clean well, equipped room. Great amenities, wonderful proximity to all the action in the village,easy parking and access throughout the facility."
United States
Michael
The price is CA $498
CA $619 total
includes taxes & fees
Nov 8 - Nov 9
Long Trail House at Stratton Mountain Resort
Property grounds

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

3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
Halifax
10.0 out of 10, Exceptional, (2 reviews)
"This place was honestly amazing. All secluded and even with how far away the cabin was from the main road the cabin had everything you could imagine and everything felt perfect. 10/10 would return"
United States
Justin M.
The price is CA $260
CA $677 total
includes taxes & fees
Nov 9 - Nov 10
3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
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

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
8.4 out of 10, Very good, (7 reviews)
"This apartment is very efficient and really wowed everyone based on the automotive inspired design. It was an impeccable space, well stocked, and the beds were even extremely comfortable. We enjoyed the bar/grill within walking distance, too. Would stay here again. "
United States
Ben B.
The price is CA $510
CA $835 total
includes taxes & fees
Nov 8 - Nov 9
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
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

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
The price is CA $126
CA $396 total
includes taxes & fees
Nov 15 - Nov 16
Cozy 3 bedroom condo 2.5 miles to Mount Snow
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

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (6 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is CA $140
CA $177 total
includes taxes & fees
Nov 9 - Nov 10
The Eagles Wing at The CHM - Private Apartment
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

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
The price is CA $124
CA $320 total
includes taxes & fees
Nov 9 - Nov 10
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
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

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is CA $89
CA $428 total
includes taxes & fees
Nov 8 - Nov 9
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
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

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.8 out of 10, Exceptional, (13 reviews)
"Nice place"
United States
Tom
The price is CA $160
CA $198 total
includes taxes & fees
Nov 8 - Nov 9
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

20. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (27 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is CA $289
CA $502 total
includes taxes & fees
Nov 9 - Nov 10
Modern Downtown Escape HotTub Fire Pit Games 12ppl
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 Brattleboro Hotel Reviews

A modern living room with a fireplace, large windows, and a cozy seating area.
Inn At Mount Snow

Inn At Mount Snow

Inn At Mount Snow
West Dover

10/10 Excellent

Tout était parfait endroit que je vais retourné sans hésiter. Nous réservons environ 40 hôtels par année et c'est de loin notre coup de coeur
Canada
marco
Reviewed September 10, 2026
Inn At Mount Snow

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Brattleboro vacation rentals we have selected for you start as low as CA $88 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 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.