Photo by Shirley Rhodes

Brattleboro Vacation Rentals

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Vacation Rentals in Brattleboro

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (49)
"This property was so clean and amazing. We heard the sounds of the creek across the road as soon as we pulled up. It was so peaceful and relaxing. The hosts were so kind and caring. Highly recommend if you are looking for a quiet and cozy place to stay. "
The Jelly Mill-A 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

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Great place with an elite game room. "
GAMERS HAVEN, River Wine Inn!

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (156)
"Two friends and I stayed at this house for the second year in a row. It has been a perfect place for us, being 10 minutes away from Grafton and 25 minutes from Okemo."
The price is CA $236
CA $503 total
includes taxes & fees
Apr 28 - Apr 29
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

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 CA $440
CA $548 total
includes taxes & fees
May 7 - May 8
Long Trail House at Stratton Mountain Resort

Wilmington Vacation Rental Near Hiking and Skiing!

9.4 out of 10, Exceptional, (19)
"We had a great time at this cabin, and the town of Wilmington had great spots for food and it's own charm. We'd definitely stay again. "
Wilmington Vacation Rental Near Hiking and Skiing!

Riverfront 2 Bedroom Unit 2

9.6 out of 10, Exceptional, (17)
"Overall, not bad. The host seems thoughtful about what the leave for you to use, but the apartment and exterior could use some TLC"
Riverfront 2 Bedroom Unit 2

Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

10.0 out of 10, Exceptional, (36)
"My husband and I absolutely loved our stay. Such care and love has gone into Fiddlers Rest. Lulu spoke to my husband and she was absolutely lovely.The fog was thick and it rained. We built a fire and my husband finished a book! We explored in the rain and love all the treasures on the land.We did have a problem with the sight on paying for our pet. We texted and called and made the decision to bring her. Lulu told us to leave the money and a note, so it all worked out.Thank-you for your...
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

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

9.4 out of 10, Exceptional, (22)
"The 2 houses were able to accommodate 21 people and 2 dogs. There was plenty of room and the houses were clean. House included linens and a few towels in each bedroom. The grounds are beautiful and it was nice to walk around and take in the scenery. We came here to ski at mt snow and was about 13 minutes to the mountain. The weather was real cold in the low single digits and they got hit with a foot of snow a few days earlier. We had 5 vehicles and Parking was a little tight. This was...
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

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

8.8 out of 10, Excellent, (47)
"Stayed twice would stay again"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (21)
"Adorable apartment and was perfect to stay in for a work trip. Clean, comfortable, and cozy. The hosts were very communicative and helpful. "
The price is CA $132
CA $246 total
includes taxes & fees
Apr 28 - Apr 29
Lovely 2nd Floor Apartment

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

10.0 out of 10, Exceptional, (22)
"Great location close to the slopes. Clean and comfortable. Loved the fireplace. "
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

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

8.8 out of 10, Excellent, (23)
"Wonderful location and comfortable. Appliances were a bit dated, but that didn’t impact our stay. The unit was not cleaned from the previous occupants upon our check in and took a few hours to do so. This is not the fault of the owner, but did impact our initial experience. Overall wonderful though. Great location and comfortable with a working fireplace. Would stay here again. "
The price is CA $98
CA $387 total
includes taxes & fees
Apr 26 - Apr 27
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Bear Creek Cabin

9.8 out of 10, Exceptional, (29)
"Enjoyed our stay"
The price is CA $554
CA $828 total
includes taxes & fees
Apr 26 - Apr 27
Bear Creek Cabin

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (71)
"Highly recommend this charming, historic place.  Well appointed. Has everything you need for your stay.  Cozy…yet plenty of space for everyone.  Looks like it was just renovated.  Took my daughter and two granddaughters for a ski weekend.  Wouldn’t hesitate to come back here.  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site

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+

Cozy 2-bedroom Unit with private backyard

10.0 out of 10, Exceptional, (22)
"4 apt complex with only one apt livable it seemed. Easy to access. Close to town, had everything we needed. No complaints except could use some hooks and lamps.... Thanks for the stay!!!"
Cozy 2-bedroom Unit with private backyard

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (29)
"The cabin was great, beautiful surroundings. Very nice house."
Jacksonville Cabin w/ Wraparound Deck & Views

Serene 2-bedroom apartment in North Adams.Plenty of off street parking.

10.0 out of 10, Exceptional, (2)
"This apartment is roomy and fully appointed. Because of some physical issues we were unable to use the queen bed...it was too high. However, the twin beds were very comfy. The location is just right. So close to the Mohawk Trail, VT border and all the wonderful businesses that revolve around art. Our visits with family and friends were made even better because of our carefree accommodations! Thank you...SandyPeggi & Rick"
The price is CA $187
CA $319 total
includes taxes & fees
May 7 - May 8
Serene 2-bedroom apartment in North Adams.Plenty of off street parking.

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

8.8 out of 10, Excellent, (43)
"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
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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Other types of properties in Brattleboro you may be interested in

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (814)
"Robert the guest service person was extremely professional and friendly when we checked in. The room was clean. The breakfast was adequate. Had an issue hooking up to the WiFI - also the pool wasn’t available- we did tell the front desk in the morning that the tub was not draining. We hadn’t brought our swim suits so no pool wasn’t an issue. We will be happy to stay there again"
The price is CA $164
CA $181 total
includes taxes & fees
Apr 29 - Apr 30
Hampton Inn Brattleboro

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1002)
"A little steep on nightly accommodation pricing considering the shape things are in which is "in disrepair". Staff was excellent, room okay. I would consider staying again but only if you are negotiable on the nightly rate. "
The price is CA $136
CA $150 total
includes taxes & fees
May 11 - May 12
Colonial Motel And Spa

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (620)
"I was staying for one night with my family. We were greeted kindly by the hostess and had an adequate breakfast in the morning. My 10-year-old daughter and I tried to use the pool, but it was quite quite chilly. Perhaps they could add a heated pool or something. The gym was enough for me and my daughter to use."
The price is CA $158
CA $174 total
includes taxes & fees
Apr 28 - Apr 29
Comfort Inn & Suites Brattleboro I-91
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.

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 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 19 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 Harris Hill Ski Jump.

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.