A calm lake reflecting a forest with autumn foliage.

Brattleboro Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Brattleboro vacation rentals

Living area

1. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.0 out of 10, Wonderful, (2 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 ￥24,777
￥70,398 total
includes taxes & fees
Sep 7 - Sep 8
Stunning Glass House nestled in the Vermont wilderness!
Private kitchen

2. 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, (4 reviews)
"What a great get away spot. Such a charming little cabin. The fireflies in the evening were a delight. Clean and cozy."
United States
s p.
The price is ￥18,067
￥39,507 total
includes taxes & fees
Sep 2 - Sep 3
The Studio with a View. Bring your dog, too!
Terrace/patio

3. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is ￥43,813
￥54,374 total
includes taxes & fees
Aug 19 - Aug 20
Vikings Villages Resort - Double Bed Room
Terrace/patio

4. 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, (17 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is ￥14,339
￥25,066 total
includes taxes & fees
Aug 24 - Aug 25
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Property grounds

5. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.4 out of 10, Exceptional, (6 reviews)
"Cozy and clean yurt in the woods surrounded by sounds of hooting owls and a super friendly and help host made for the perfect family weekend. Can’t wait to plan another stay. Made roughing it not rough at all. "
United States
Allisha C.
The price is ￥10,754
￥20,312 total
includes taxes & fees
Aug 31 - Sep 1
Yurt Oasis in the woods of Hinsdale, NH
Outdoor dining

6. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is ￥8,763
￥12,966 total
includes taxes & fees
Aug 18 - Aug 19
2 private mountain RV pads for rent. Full hook ups
In-room safe, iron/ironing board, WiFi, bed sheets

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is ￥32,979
￥106,112 total
includes taxes & fees
Aug 18 - Aug 19
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Interior

8. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (61 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is ￥18,497
￥32,407 total
includes taxes & fees
Aug 18 - Aug 19
Lovely 2nd Floor Apartment
Property grounds

9. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (63 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is ￥27,530
￥50,639 total
includes taxes & fees
Sep 1 - Sep 2
Family Friendly Hilltop House In Putney Vermont
Outdoor pool, a heated pool

10. 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 ￥10,840
￥50,595 total
includes taxes & fees
Sep 8 - Sep 9
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior detail

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
9.6 out of 10, Exceptional, (9 reviews)
"We had a great"
United States
Meredith B.
The price is ￥17,924
￥43,334 total
includes taxes & fees
Aug 31 - Sep 1
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Exterior

12. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (14 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is ￥22,051
￥72,584 total
includes taxes & fees
Aug 31 - Sep 1
Chalet Mount Snow/Stratton Skiing/hiking
1 bedroom, desk, iron/ironing board, WiFi

13. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is ￥18,162
￥32,566 total
includes taxes & fees
Sep 13 - Sep 14
Balcony Room in Victorian Home private bath
Beach

14. 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)
"Fire place was awesome! Great place to stay! Had everything in the kitchen we needed. All the beds were comfy! "
United States
Susan S.
The price is ￥12,905
￥45,548 total
includes taxes & fees
Aug 31 - Sep 1
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Coffee/tea maker, fridge, microwave, oven

15. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (25 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is ￥25,730
￥51,772 total
includes taxes & fees
Aug 18 - Aug 19
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Exterior

16. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is ￥19,118
￥34,167 total
includes taxes & fees
Aug 18 - Aug 19
Private bed with En-suite bathroom Marigold Room
Coffee/tea maker, fridge, microwave, oven

17. 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.
The price is ￥31,864
￥78,999 total
includes taxes & fees
Aug 18 - Aug 19
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Exterior

18. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (170 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is ￥27,084
￥58,527 total
includes taxes & fees
Aug 18 - Aug 19
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Iron/ironing board, WiFi, bed sheets

19. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is ￥25,651
￥58,195 total
includes taxes & fees
Aug 24 - Aug 25
Cozy private 2 bed apartment in Shelburne Falls
Smart TV, fireplace, Netflix, streaming services

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
9.6 out of 10, Exceptional, (27 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is ￥23,229
￥76,837 total
includes taxes & fees
Sep 1 - Sep 2
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

8/10 Good
"Rooms were clean and comfortable. Breakfast was good. Wonderful to be able to sit outside in common area and if on first floor right outside your room. The restaurant attached was great."
Karen 2-night trip
Posted less than an hour ago
Best Western Plus Keene Hotel

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:

  • View our selection of featured holiday rentals in Brattleboro
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  • Enter your travel dates to view the best deals on holiday rentals in Brattleboro while they last

Look no further and take a look at our great range of rental properties in Brattleboro!

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 28 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 Brattleboro Museum & Art Center. 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.