Brattleboro Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Brattleboro holiday 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 HK$565
HK$745 total
includes taxes & fees
30 Nov - 1 Dec
Cozy Vermont Tiny Home Get Away
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

2. 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 HK$1,036
HK$3,076 total
includes taxes & fees
18 Nov - 19 Nov
Stunning Glass House nestled in the Vermont wilderness!
A wooden interior with a kitchen, bar area, and dining space.

3. 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, (9 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 HK$897
HK$1,769 total
includes taxes & fees
18 Nov - 19 Nov
The Studio with a View. Bring your dog, too!
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
The price is HK$2,157
HK$2,537 total
includes taxes & fees
15 Nov - 16 Nov
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
The price is HK$706
HK$1,166 total
includes taxes & fees
17 Nov - 18 Nov
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

6. 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 HK$1,334
HK$2,223 total
includes taxes & fees
23 Nov - 24 Nov
Wellness Getaway with a Personal Sauna, and Private River Beach!
A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

7. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (7 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is HK$784
HK$993 total
includes taxes & fees
15 Nov - 16 Nov
The Eagles Wing at The CHM - Private Apartment
A blue house with a porch, a wooden bench, and a door.

8. 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 HK$699
HK$1,797 total
includes taxes & fees
18 Nov - 19 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A wooden house with a porch lit by string lights, surrounded by snow.

9. 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 HK$689
HK$3,011 total
includes taxes & fees
15 Nov - 16 Nov
Chalet Mount Snow/Stratton Skiing/hiking
A garden with a wooden pergola, purple flowers, and a river view.

10. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (66 reviews)
"Had a perfect, relaxing stay in this gorgeous spot. Everything was terrific. Highly recommend!"
United States
Wendy B.
The price is HK$1,263
HK$2,232 total
includes taxes & fees
17 Nov - 18 Nov
Family Friendly Hilltop House In Putney Vermont
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

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

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is HK$722
HK$1,341 total
includes taxes & fees
15 Nov - 16 Nov
2 Twin beds on 1st floor with En-suite bathroom.
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.
The price is HK$530
HK$2,389 total
includes taxes & fees
15 Nov - 16 Nov
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A calm lake with a wooden boat on the shore.

13. 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 HK$784
HK$2,296 total
includes taxes & fees
1 Dec - 2 Dec
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

14. 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.
The price is HK$926
HK$2,854 total
includes taxes & fees
14 Nov - 15 Nov
Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

15. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (74 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is HK$1,200
HK$1,866 total
includes taxes & fees
17 Nov - 18 Nov
Lovely 2nd Floor Apartment
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

16. 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.
The price is HK$741
HK$1,162 total
includes taxes & fees
18 Nov - 19 Nov
Yurt Oasis in the woods of Hinsdale, NH
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
The price is HK$902
HK$1,551 total
includes taxes & fees
15 Nov - 16 Nov
Private room with En-suite bathroom Marigold Room
A spacious cabin with a wooden interior, a dining area, a sofa, and a fireplace.

18. Cozy Cedar Cabin 8 Min to Mount Snow

Cozy Cedar Cabin 8 Min to Mount Snow
Dover
The price is HK$1,364
HK$4,910 total
includes taxes & fees
22 Nov - 23 Nov
Cozy Cedar Cabin 8 Min to Mount Snow
A rural landscape with a house surrounded by autumn foliage and a river.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is HK$1,353
HK$4,620 total
includes taxes & fees
15 Nov - 16 Nov
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
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 out more about Brattleboro

Search for holiday rentals in Brattleboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Brattleboro using one of the methods below:

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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.