A calm lake reflecting a forest with autumn foliage.

Brattleboro Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Brattleboro vacation rentals

A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

1. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
$92 nightly
The price is $104
Oct 31 - Nov 1
Total with taxes and fees
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.
$458 nightly
The price is $513
Nov 8 - Nov 9
Total with taxes and fees
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
10.0 out of 10, Exceptional, (6 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.
$240 nightly
The price is $268
Oct 25 - Oct 26
Total with taxes and fees
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
$336 nightly
The price is $341
Oct 12 - Oct 13
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
A rustic cabin with a covered porch, a small shed, and outdoor seating.

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, (19 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
$145 nightly
The price is $157
Oct 25 - Oct 26
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, (12 reviews)
"What an amazing Yurt. The location was so peaceful. The yurt and outhouse was super clean. Hosts were friendly and helpful. I would stay again if in the area."
United States
Troy H.
$136 nightly
The price is $148
Oct 13 - Oct 14
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.
$254 nightly
The price is $284
Nov 3 - Nov 4
Total with taxes and fees
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, (64 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.
$227 nightly
The price is $255
Oct 20 - Oct 21
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
A blue house with a porch, a wooden bench, and a door.

9. 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
9.2 out of 10, Wonderful, (10 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
$214 nightly
The price is $239
Oct 25 - Oct 26
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A lakeside park with picnic tables and a concrete walkway.

10. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
$75 nightly
The price is $81
Oct 12 - Oct 13
Total with taxes and fees
2 private mountain RV pads for rent. Full hook ups
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

11. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
$140 nightly
The price is $158
Oct 15 - Oct 16
Total with taxes and fees
The Eagles Wing at The CHM - Private Apartment
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

12. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (69 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
$207 nightly
The price is $231
Nov 1 - Nov 2
Total with taxes and fees
Lovely 2nd Floor Apartment
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.
$271 nightly
The price is $306
Nov 1 - Nov 2
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

14. 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.
$271 nightly
The price is $306
Oct 27 - Oct 28
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.

15. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
$170 nightly
The price is $190
Nov 4 - Nov 5
Total with taxes and fees
2 Twin beds on 1st floor with En-suite bathroom.
A two-story house with a front porch, a staircase, and a small garden area.

16. Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene
Keene
9.6 out of 10, Exceptional, (8 reviews)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
$155 nightly
The price is $168
Oct 19 - Oct 20
Total with taxes and fees
Central Large 2-bedrooms with office in Keene
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

17. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
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.
$320 nightly
The price is $362
Oct 12 - Oct 13
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

18. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
$206 nightly
The price is $230
Nov 10 - Nov 11
Total with taxes and fees
Private bed with En-suite bathroom Marigold Room
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

19. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (4 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
$442 nightly
The price is $480
Oct 12 - Oct 13
Total with taxes and fees
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A spacious living area with a brown leather sofa, a wooden coffee table, and wicker chairs. A staircase leads to an upper level.

20. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.4 out of 10, Exceptional, (29 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
$413 nightly
The price is $467
Oct 19 - Oct 20
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
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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Top Brattleboro Hotel Reviews

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Very clean, breakfast was very good. And the restaurant attached to the hotel was amazing"
James 2-night trip
Posted 5 hours ago
Best Western Plus Keene Hotel

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 $224 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.

Explore a world of travel with Expedia

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.