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Brattleboro Vacation Rentals

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Sep 28 - Sep 29
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Vacation Rentals in Brattleboro

The Jelly Mill-A Peaceful River Retreat
Exterior

The Jelly Mill-A Peaceful River Retreat

10.0 out of 10, Exceptional, (59)
"Very much off the beaten path, but lets you experience the beauty of Vermont. Quiet and peaceful. A beautiful little property that served our needs perfectly. Would definitely come back."
The Jelly Mill-A Peaceful River Retreat
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Outdoor dining

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

8.4 out of 10, Very Good, (58)
"Great location and super cute"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Bear Creek Cabin
Exterior

Bear Creek Cabin

9.8 out of 10, Exceptional, (39)
"We enjoyed our stay!!"
The price is ￥59,796
￥87,665 total
includes taxes & fees
Oct 4 - Oct 5
Bear Creek Cabin
Long Trail House at Stratton Mountain Resort
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
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is ￥42,806
￥53,208 total
includes taxes & fees
Oct 28 - Oct 29
Long Trail House at Stratton Mountain Resort
Owl's Nest Treehouse
Property grounds

Owl's Nest Treehouse

10.0 out of 10, Exceptional, (8)
"This place is beautiful! It had everything we needed. The hosts were very communicative and encouraged us to contact them if we had any questions. We stayed at the treehouse to celebrate our 30th anniversary and it exceeded our expectations. I would highly recommend this cozy and quiet retreat."
The price is ￥41,110
￥50,120 total
includes taxes & fees
Sep 29 - Sep 30
Owl's Nest Treehouse
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Interior

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

10.0 out of 10, Exceptional, (5)
"We had a wonderful stay."
The price is ￥49,107
￥84,041 total
includes taxes & fees
Sep 29 - Sep 30
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Lovely ski-in/out condo steps from ski lift with trails and amazing views
TV, fireplace

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

8.4 out of 10, Very Good, (25)
"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 ￥11,212
￥41,094 total
includes taxes & fees
Sep 29 - Sep 30
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (162)
"We very much enjoyed our stay, check in was a breeze and we found the cabin to be a cozy retreat. We have been looking for a place that had a bed and bath on first floor to accommodate some mobility limitations and this home was perfect having a single step on the front porch. We look forward to booking another trip with this host "
The price is ￥25,413
￥54,581 total
includes taxes & fees
Sep 29 - Sep 30
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Peaceful getaway at Stratton View Lodge
Fridge, microwave, oven, stovetop

Peaceful getaway at Stratton View Lodge

8.0 out of 10, Very Good, (1)
"It was a beautiful house only ten minutes from Stratton! Plenty of rooms with comfortable beds. They provided towels and soaps and all the necessities. However one of the reasons that we booked this house specifically was because it had a hot tub. The hot tub was unusable the entire weekend. You had to hop over a wire to get to the hot tub. The hot tub was ice cold. We couldn’t find the settings to try to turn it up. It seemed to be on but never got any warmer. There was supposedly an...
Peaceful getaway at Stratton View Lodge
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Interior

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (7)
"Great house, great location, Great communication with Todd. Will be back for sure!!!! Thanks for everything Todd. "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Beautiful Lodging at Mount Snow with Hot Tub on Deck
Property grounds

Beautiful Lodging at Mount Snow with Hot Tub on Deck

9.4 out of 10, Exceptional, (42)
"Real Vermont feel. Pretty and nice quiet neighborhood!"
Beautiful Lodging at Mount Snow with Hot Tub on Deck
Lovely 2nd Floor Apartment
Interior

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (36)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
The price is ￥17,356
￥30,075 total
includes taxes & fees
Sep 29 - Sep 30
Lovely 2nd Floor Apartment
Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq
Fridge, microwave, oven, stovetop

Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq

10.0 out of 10, Exceptional, (5)
"My friends and I had an awesome weekend staying here. The house itself was gorgeous - the view was great, interior design and feel were cozy and beautiful, and we had a lot of space. The showers were a favorite among the group. We did several hikes and swam at a swimming hole, all on the property. It was also within driving distance of other awesome hikes too (waterfalls, etc.). The hosts had a lot of helpful information and suggestions about the area and things to do. We will definitely be...
Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Interior

Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

10.0 out of 10, Exceptional, (84)
"A beautiful cabin in the woods. Very clean and a perfect stay."
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Treetop townhouse with Hot Tub and plenty of space for the whole family!
Smart TV, fireplace, books

Treetop townhouse with Hot Tub and plenty of space for the whole family!

5.4 out of 10, (3)
"We arrived at our rental at 4:05pm (check-in was at 4pm) and were met by the management company. They just started to clean the rental, due to cleaners canceling. They did not contact us to let us know the rental would not be ready. They allowed us to settled in. They finished cleaning about 30 minutes later. I specially asked if they were finished with everything and they replied yes. The next morning I woke up and had an asthma attack. I realized there was dog hair everywhere. I...
Treetop townhouse with Hot Tub and plenty of space for the whole family!
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Interior

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

10.0 out of 10, Exceptional, (224)
"Great house, fantastically well equipped (kayaks, bikes etc). Excellent, very responsive host. View out over the lake is amazing. Really enjoyed our stay. "
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Lake life at Woodford Cottage
Smart TV, fireplace

Lake life at Woodford Cottage

9.6 out of 10, Exceptional, (15)
"Perfect getaway for a family ski trip."
Lake life at Woodford Cottage
Spacious Riverfront Home 7 Minutes to Stratton!
Fridge, microwave, oven, stovetop

Spacious Riverfront Home 7 Minutes to Stratton!

10.0 out of 10, Exceptional, (33)
"Perfect house for a few families to gather and have fun. "
Spacious Riverfront Home 7 Minutes to Stratton!
Secluded Mountain Retreat: Gorgeous Views, Five Mins to Stratton, Sauna, Firepit
Property grounds

Secluded Mountain Retreat: Gorgeous Views, Five Mins to Stratton, Sauna, Firepit

2.0 star property
9.2 out of 10, Wonderful, (9)
"No hassles great place as described in listing. Clean and has all necessary amenities. Would happily stay there again "
The price is ￥44,847
￥112,334 total
includes taxes & fees
Oct 16 - Oct 17
Secluded Mountain Retreat: Gorgeous Views, Five Mins to Stratton, Sauna, Firepit
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Smart TV, fireplace, foosball, table tennis

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

10.0 out of 10, Exceptional, (53)
"Consistently great time at this place (3rd time there)"
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
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

Colonel Williams Inn

Colonel Williams Inn

10/10 Excellent
"This property is very quaint and welcoming. The proprietors were so friendly and helpful and went out of their way to make sure we were comfortable. Not only did we have a wonderful anniversary weekend, we made great new friends. And the breakfasts were absolutely delicious! I highly recommend the colonel wilkiams inn!!!"
Ervin 3-night trip
Posted 4 days ago
Colonel Williams Inn

Find out more about Brattleboro

Find out more about Brattleboro

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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?

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 20 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 Tasha Tudor Museum. 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.