Brattleboro Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

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.
$83 nightly
The price is $94
Nov 30 - Dec 1
Total with taxes and fees
Cozy Vermont Tiny Home Get Away
A wooden interior with a kitchen, bar area, and dining space.

2. 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.
$207 nightly
The price is $232
Nov 18 - Nov 19
Total with taxes and fees
The Studio with a View. Bring your dog, too!
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

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.
$348 nightly
The price is $390
Nov 18 - Nov 19
Total with taxes and fees
Stunning Glass House nestled in the Vermont wilderness!
A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

4. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
$311 nightly
The price is $313
Nov 8 - Nov 9
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
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
$141 nightly
The price is $153
Nov 19 - Nov 20
Total with taxes and fees
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

6. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (13 reviews)
"Enjoyed my stay"
United States
Ian C.
$132 nightly
The price is $143
Nov 9 - Nov 10
Total with taxes and fees
Yurt Oasis in the woods of Hinsdale, NH
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.
$241 nightly
The price is $270
Nov 16 - Nov 17
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
A wooden house with a porch lit by string lights, surrounded by snow.

8. 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.
$312 nightly
The price is $353
Nov 8 - Nov 9
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
A garden with a wooden pergola, purple flowers, and a river view.

9. 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.
$233 nightly
The price is $261
Nov 8 - Nov 9
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

10. 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.
$109 nightly
The price is $123
Nov 9 - Nov 10
Total with taxes and fees
The Eagles Wing at The CHM - Private Apartment
A blue house with a porch, a wooden bench, and a door.

11. 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.
$198 nightly
The price is $221
Nov 9 - Nov 10
Total with taxes and fees
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.

12. 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.
$260 nightly
The price is $294
Nov 8 - Nov 9
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

13. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
$149 nightly
The price is $166
Nov 8 - Nov 9
Total with taxes and fees
2 Twin beds on 1st floor with En-suite bathroom.
A house with a staircase leading to a porch, surrounded by snow and string lights.

14. 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
$123 nightly
The price is $138
Nov 8 - Nov 9
Total with taxes and fees
Light-filled treetop apartment close to downtown Greenfield and Highland Park
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.
$241 nightly
The price is $272
Nov 16 - Nov 17
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

16. 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
$207 nightly
The price is $231
Nov 8 - Nov 9
Total with taxes and fees
Lovely 2nd Floor Apartment
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

17. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
$172 nightly
The price is $192
Nov 8 - Nov 9
Total with taxes and fees
Private room with En-suite bathroom Marigold Room
Property grounds

18. 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.
$422 nightly
The price is $473
Nov 9 - Nov 10
Total with taxes and fees
3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

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

Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
$316 nightly
The price is $357
Nov 8 - Nov 9
Total with taxes and fees
Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
A spacious cabin with a wooden interior, a dining area, a sofa, and a fireplace.

20. Cozy Cedar Cabin 8 Min to Mount Snow

Cozy Cedar Cabin 8 Min to Mount Snow
Dover
$543 nightly
The price is $613
Nov 15 - Nov 16
Total with taxes and fees
Cozy Cedar Cabin 8 Min to Mount Snow
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.
View all properties

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Top Brattleboro Hotel Reviews

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

Vikings Villages Resort

Vikings Villages Resort
Guilford

10/10 Excellent

I would leave all my possessions behind to live in this cabin forever.
United States
Diego
Reviewed April 28, 2024
Vikings Villages Resort

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 $93 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.

Explore a world of travel with Expedia