A calm lake reflecting a forest with autumn foliage.

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Brattleboro holiday rentals

House (3 Bedrooms) | Front of property

1. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
The price is 4.593.750 ₫
11.411.138 ₫ total
includes taxes & fees
11 Aug - 12 Aug
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Outdoor spa tub

2. Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is 8.245.125 ₫
10.248.690 ₫ total
includes taxes & fees
10 Aug - 11 Aug
Long Trail House at Stratton Mountain Resort
Exterior

3. Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is 4.539.544 ₫
11.773.103 ₫ total
includes taxes & fees
13 Aug - 14 Aug
Two Brooks Lodge
House (4 Bedrooms) | Interior

4. 3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
The price is 9.975.000 ₫
17.154.113 ₫ total
includes taxes & fees
9 Aug - 10 Aug
3 Mi to Mount Snow: Spacious West Dover Home
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

Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"Absolute gem of a stay. Every little detail was thought of ! Easy check in and out ! Close to a small general store and great ice cream shop! Worth a visit !! So unique ! Cabin was immaculate and decorated so tasteful !"
Sara 1-night trip
Posted 21 hours ago
Vikings Villages Resort

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.

How many holiday rentals are there in Brattleboro?

Expedia has 28 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 Harris Hill Ski Jump.

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.