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 NZ$171
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 NZ$687
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, (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 NZ$405
includes taxes & fees
18 Nov - 19 Nov
The Studio with a View. Bring your dog, too!
A rustic log cabin with a steeply pitched roof, a prominent door with a decorative cross, and a small porch with two Adirondack chairs.

4. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is NZ$573
includes taxes & fees
15 Nov - 16 Nov
Vikings Villages Resort - Double Bed Room
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.

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 NZ$252
includes taxes & fees
19 Nov - 20 Nov
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A wooden staircase leading up to a wooden bridge in a forested area.

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 NZ$497
includes taxes & fees
17 Nov - 18 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 NZ$226
includes taxes & fees
13 Nov - 14 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 NZ$408
includes taxes & fees
18 Nov - 19 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A deck with a fire pit, chairs, and a table.

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 NZ$686
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 NZ$505
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 NZ$305
includes taxes & fees
16 Nov - 17 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 NZ$565
includes taxes & fees
16 Nov - 17 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 NZ$498
includes taxes & fees
18 Nov - 19 Nov
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 NZ$647
includes taxes & fees
13 Nov - 14 Nov
Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
A wooden door with a mirror, a small basket with dried flowers, and a light switch on the wall.

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 NZ$426
includes taxes & fees
17 Nov - 18 Nov
Lovely 2nd Floor Apartment
A wooden deck with a grill and propane tank, surrounded by trees.

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 NZ$266
includes taxes & fees
18 Nov - 19 Nov
Yurt Oasis in the woods of Hinsdale, NH
A dining room with a wooden table, chairs, a fireplace, a bookcase, and a stained glass ceiling light.

17. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is NZ$353
includes taxes & fees
15 Nov - 16 Nov
Private room with En-suite bathroom Marigold Room
A log cabin with a deck, a fire pit, and an American flag.

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.
The price is NZ$879
includes taxes & fees
17 Nov - 18 Nov
3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
A wooden deck with outdoor furniture and string lights.

19. Cozy Cedar Cabin 8 Min to Mount Snow

Cozy Cedar Cabin 8 Min to Mount Snow
Dover
The price is NZ$1,092
includes taxes & fees
18 Nov - 19 Nov
Cozy Cedar Cabin 8 Min to Mount Snow
A rural landscape with a house surrounded by autumn foliage and a river.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is NZ$1,018
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 holiday rentals that suit your style

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Top Brattleboro Hotel Reviews

A dock extending into a calm lake, surrounded by lush greenery.
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
West Chesterfield

8/10 Good

Pleasant stay hotel was empty when we arrived but filled up a bit by evening.
Australia
Jen123
Reviewed August 30, 2014
Riverside Hotel, an Ascend Collection Hotel

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, 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 NZ$170 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.