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Top Holiday Rentals in Brattleboro

The Jelly Mill-A Peaceful River Retreat

10.0 out of 10, Exceptional, (52)
"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

Hike & Swim On-Site: Cozy Falls Brook Cabin

10.0 out of 10, Exceptional, (10)
"Great little cabin, would definitely stay again!"
Hike & Swim On-Site: Cozy Falls Brook Cabin

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 £302
includes taxes & fees
3 Jul - 4 Jul
Long Trail House at Stratton Mountain Resort

Riverfront 2 Bedroom Unit 2

9.6 out of 10, Exceptional, (19)
"We had a lovely time in central Mass"
Riverfront 2 Bedroom Unit 2

Bear Creek Cabin

9.8 out of 10, Exceptional, (30)
"Enjoyed our stay"
The price is £437
includes taxes & fees
29 Jun - 30 Jun
Bear Creek Cabin

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (17)
"This place was perfect for our stay! It was clean, nicely decorated/designed and had thoughtful touches. The pictures were spot on for what to expect, it was peaceful, and the view was lovely. Crystal was great and check-in/out was easy! We would definitely stay here again."
Lakefront Orange Vacation Rental - Pet Friendly!

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

10.0 out of 10, Exceptional, (20)
"Beautiful location and so many cozy touches throughout home!"
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

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 £274
includes taxes & fees
2 Jul - 3 Jul
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

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!

The Mountain Escape!

9.8 out of 10, Exceptional, (17)
"It was a perfect house and great location! Would definitely stay again!"
The price is £572
includes taxes & fees
7 Jul - 8 Jul
The Mountain Escape!

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!

Private Family Estate for any Season

10.0 out of 10, Exceptional, (66)
"Beautiful place and great location."
Private Family Estate for any Season

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (128)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Lovely ski-in/out condo steps from ski lift with trails and amazing views

8.8 out of 10, Excellent, (23)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
The price is £221
includes taxes & fees
26 Jun - 27 Jun
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Downtown Hot Tub Escape

9.4 out of 10, Exceptional, (13)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is £371
includes taxes & fees
29 Jun - 30 Jun
Downtown Hot Tub Escape

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

9.4 out of 10, Exceptional, (22)
"ideal for a large group of adult friends "
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

10.0 out of 10, Exceptional, (1)
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

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

8.8 out of 10, Excellent, (47)
"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

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

10.0 out of 10, Exceptional, (48)
"Consistently great time at this place (3rd time there)"
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (26)
"Easy stay, good location for us. Would stay again. "
The price is £137
includes taxes & fees
2 Jul - 3 Jul
Lovely 2nd Floor Apartment
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 18 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 Latchis Theatre and Vermont Marketplace.

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.