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Brattleboro Holiday Rentals

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Check prices for these dates

Tonight
9 Jul - 10 Jul
Tomorrow
10 Jul - 11 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Brattleboro

The Jelly Mill-A Peaceful River Retreat
Stroll up to this charming home surrounded by lush greenery and a well-manicured lawn.

The Jelly Mill-A Peaceful River Retreat

10.0 out of 10, Exceptional, (53)
"Great location, communicative and welcoming hosts, and great amenities. We loved grilling and using the firepit. The surrounding area is great to walk around in. Easy drive from here to Mt Snow."
The Jelly Mill-A Peaceful River Retreat
Long Trail House at Stratton Mountain Resort
Relax by the pool surrounded by lush trees and a distant church spire.

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is HK$2,601
HK$3,232 total
includes taxes & fees
10 Jul - 11 Jul
Long Trail House at Stratton Mountain Resort
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Relax by the campfire in a serene wooded setting, surrounded by Adirondack chairs and a rustic picnic table.

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (49)
"really enjoyed our stay. Place would be much better if there was a microwave."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Lovely 2nd Floor Apartment
Relax in a serene space with a comfortable armchair, console table, and lush greenery.

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (30)
"Easy stay, good location for us. Would stay again. "
The price is HK$934
HK$1,605 total
includes taxes & fees
28 Jul - 29 Jul
Lovely 2nd Floor Apartment
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Situated amidst a serene landscape, this charming house features a covered porch, a chimney, and a small front porch with a bench.

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (157)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is HK$1,334
HK$2,875 total
includes taxes & fees
10 Jul - 11 Jul
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
Cozy cabin retreat with a high ceiling, central fireplace, and comfortable seating area.

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

10.0 out of 10, Exceptional, (21)
"Beautiful location and so many cozy touches throughout home!"
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!
Fully equipped kitchen with stainless steel appliances, dark cabinets, and a white tiled backsplash.

8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

8.0 out of 10, Very good, (1)
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Escape to a serene cabin retreat surrounded by trees and a seasonal touch.

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

10.0 out of 10, Exceptional, (4)
"We had a magical time at the yurt! Very sweet and rustic but comfortable. Great secluded location but close enough to restaurants and Brattleboro. We will definitely be back. "
The price is HK$1,020
HK$1,508 total
includes taxes & fees
2 Aug - 3 Aug
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Cozy living area with a leather sofa, wooden coffee table, and staircase leading to an upper level.

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

10.0 out of 10, Exceptional, (49)
"Consistently great time at this place (3rd time there)"
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
The Mountain Escape!
Enjoy cooking in this well-equipped kitchen with a refrigerator, cabinetry, and hardwood floor.

The Mountain Escape!

9.8 out of 10, Exceptional, (17)
"Good spot for catching up with friends for the weekend. Hot tub was perfect and everything was comfortable."
The price is HK$782
HK$5,852 total
includes taxes & fees
10 Jul - 11 Jul
The Mountain Escape!
Downtown Hot Tub Escape
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and oven, surrounded by dark cabinetry and a wooden countertop.

Downtown Hot Tub Escape

9.2 out of 10, Wonderful, (15)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
Downtown Hot Tub Escape
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Features an oven, microwave, and refrigerator, along with a large window and ceiling lights.

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

9.0 out of 10, Wonderful, (29)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Cozy living space with a high ceiling, fireplace, and large window.

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

9.4 out of 10, Exceptional, (14)
"Easy check in and the owner responds immediately to any questions. A really easy close drive to Berkshire East Ski Mountain. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Relax in a serene hot tub with breathtaking views of the surrounding snowy landscape.

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

8.8 out of 10, Excellent, (43)
"We enjoyed our stay at the Blue House. Its size and location cannot be beat when it comes to group trips. We will be back!"
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Rare new Home on Lake Whitingham. Semi-priv beach
Enjoy the serene view from this balcony with a wooden table and two chairs.

Rare new Home on Lake Whitingham. Semi-priv beach

10.0 out of 10, Exceptional, (1)
"This home is spectacular, built on a hillside overlooking a pond. Very tastefully built into the landscape. Inside was very well appointed and plenty of room for our family. Three bathrooms was a big plusCould have spent the entire day lookjng out the windows"
Rare new Home on Lake Whitingham. Semi-priv beach
Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+
Relax in a warm and inviting space with a pool view, comfortable seating, and a bookshelf.

Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

6.0 out of 10, (1)
"Inside property was great - house was very fun and spacious and clean . HOWEVER..the driveway clearly hadn’t been plowed for a long time when we got there and so once we pulled in our cars were stuck. We were trapped at the house for 3 days. The plow driver came to plow the neighbor and told us he hadn’t been paid by the owners so hadn’t been plowing for some time The owners finally arranged for a different plow to come but not being able to leave for 3 days really affected our ability to...
Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+
Riverside Retreat – Cozy 2-Story Getaway!
Enjoy cooking in this well-equipped kitchen with a central island, microwave, stove, and sink.

Riverside Retreat – Cozy 2-Story Getaway!

9.8 out of 10, Exceptional, (25)
"Interior amazing. Exterior could use some attention"
Riverside Retreat – Cozy 2-Story Getaway!
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Enjoy a serene forest view from the comfort of this room, featuring two beds and a cozy seating area.

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

9.4 out of 10, Exceptional, (23)
"ideal for a large group of adult friends "
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Jacksonville Cabin w/ Wraparound Deck & Views
Kitchen features a central island, wooden cabinetry, and a stainless steel refrigerator.

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (32)
"The cabin was great, beautiful surroundings. Very nice house."
Jacksonville Cabin w/ Wraparound Deck & Views
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Relax in a serene space with a large bathtub, book, and candle, accompanied by a wood-burning stove.

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay."
The price is HK$2,865
HK$4,817 total
includes taxes & fees
10 Jul - 11 Jul
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
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 holiday rentals in Brattleboro?

Yes, there are holiday rentals in Brattleboro close to Brattleboro Bowl, 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 19 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 Tasha Tudor Museum. Other places in town to visit include Vermont Marketplace and Brattleboro Bowl.

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.