Photo by Shirley Rhodes

Brattleboro Vacation Rentals

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Vacation Rentals in Brattleboro

Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (33)
"Charming house with everything we needed!"
Cozy Cottage Along Idyllic Green River
Property grounds
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
10.0 out of 10, Exceptional, (11)
"Beautiful home with everything that we needed. Short drive to Landmark College to see our daughter and close to Brattleboro shopping and restaurants. The river was also wonderful to wake up to. Highly recommend! "
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
Fridge, microwave, stovetop, coffee/tea maker
Cozy Falls Brook Cabin: Hike & Swim On-Site!
10.0 out of 10, Exceptional, (4)
"What a beautiful clean cabin nestled next to a brook with lots of hiking paths to explore. Centrally located to several ski resorts. Matt was the most excellent host! I look forward to returning during other seasons!"
Cozy Falls Brook Cabin: Hike & Swim On-Site!
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Interior
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (47)
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (24)
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (140)
"Great little house to enjoy spending time with family and all that VT has to offer. Wonderful host, we will be back."
The price is ￥26,648
￥56,383 total
includes taxes & fees
May 27 - May 28
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
TV, fireplace
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
9.2 out of 10, Wonderful, (15)
"Great location- 10-15min from Stratton, beautiful views, all the amenities. Awesome decor, will definitely be back!"
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, (69)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is ￥48,672
￥58,893 total
includes taxes & fees
Jun 4 - Jun 5
Long Trail House at Stratton Mountain Resort
Exterior
Bear Creek Cabin
10.0 out of 10, Exceptional, (13)
"Had such a wonderful stay in the beautiful Berkshires at this unique cabin property! Everything was clean and well-maintained. Very rustic and charming. We had a lot of fun by the fire and walking down to the river in the backyard. So many things to do in this area! Hiking, rafting, and dining in the nearby towns! Would definitely return!"
The price is ￥62,700
￥94,550 total
includes taxes & fees
May 28 - May 29
Bear Creek Cabin
9 bedrooms, desk, iron/ironing board, free WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.4 out of 10, Exceptional, (16)
"Our experience was average overall."
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Property grounds
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
9.0 out of 10, Wonderful, (37)
"Property was incredible. The house was beautiful and enormous. Very comfortable with a group of 22. Pool and hot tub were great."
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
TV
Dog-friendly chalet cabin with valley view, deck, and private hot tub
7.2 out of 10, Good, (14)
"We had a great weekend staying here. The projector and hot tub were awesome amenities. There was a snow storm right before we arrived and the roads were clear and the driveway was plowed. We had a great experience and would stay here again!"
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Fridge, microwave, oven, stovetop
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (28)
"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Fridge, microwave, stovetop, dishwasher
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, (23)
"Magical little place."
Jacksonville Cabin w/ Wraparound Deck & Views
Exterior
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (116)
"Another great stay at Hawley. House never disappoints. Weather even cooperated. Thanks Again Lark! Lew"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Outdoor pool, a heated pool
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
9.6 out of 10, Exceptional, (8)
"Great place. Super close to everything. Host was super helpful. Everything you need for an amazing ski weekend."
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Exterior
Green Mountain Modern House: iconic modern getaway
Green Mountain Modern House: iconic modern getaway
Fridge, microwave, oven, stovetop
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
9.6 out of 10, Exceptional, (44)
"We had a very nice stay. The house had plenty of room for our family including the living, dining, and sleeping areas. The location was great."
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
Interior
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
10.0 out of 10, Exceptional, (29)
"We had a wonderful stay. The house has everything you need!"
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
1 bedroom, iron/ironing board, free WiFi, bed sheets
Spectacular Mountain views with all the amentities nearby
9.8 out of 10, Exceptional, (40)
"It was very welcoming and comfortable! Highly recommend!"
Spectacular Mountain views with all the amentities nearby
Don't see what you're looking for?
See all available properties in Brattleboro
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.

Other types of properties in Brattleboro you may be interested in

Exterior
Colonial Motel And Spa
3.0 star property
7.0 out of 10, Good, (1001)
"Great pool and hot tub facilities with kickers"
The price is ￥15,362
￥16,898 total
includes taxes & fees
May 28 - May 29
Colonial Motel And Spa
Concierge desk
The Covered Bridge Inn
2.5 star property
8.2 out of 10, Very Good, (1002)
"The room was quiet and clean. The staff was friendly. I would stay there again. "
The price is ￥12,464
￥13,847 total
includes taxes & fees
Jun 4 - Jun 5
The Covered Bridge Inn
Lobby
Hampton Inn Brattleboro
2.5 star property
8.4 out of 10, Very Good, (902)
"Sarah at the front desk was super friendly and helpful! Clean and comfy rooms in a great location at a reasonable price. Will definitely be a go-to when traveling for work in the future!"
The price is ￥23,857
￥26,242 total
includes taxes & fees
Jun 17 - Jun 18
Hampton Inn Brattleboro
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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Frequently asked questions

Are there vacation rentals in Brattleboro?

Yes, we offer vacation rentals in Brattleboro near Brattleboro Bowl, 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?

Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly: This vacation home rental outside of Brattleboro offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Brattleboro?

Expedia has 16 vacation rentals for your stay in Brattleboro.

What can I see and do in Brattleboro?

Enjoy the outdoors at Brattleboro Common and Connecticut River, or simply take in cultural attractions like The Stone Church and Tasha Tudor Museum. Other places in town to visit include Latchis Theatre and Brattleboro Farmers' Market.

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.

Recent reviews of Brattleboro properties
Expedia verified reviews

The Putney Inn

The Putney Inn

5/5 Excellent
"Easy, quick check in, friendly staff. Some noise from neighbors to be expected. Very clean, good sleep, pleasant stay. Would return. "
A verified traveler stayed at The Putney Inn
Posted 3 days ago
The Putney Inn