Photo by Shirley Rhodes

Brattleboro Holiday Rentals

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Holiday Rentals in Brattleboro

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (43)
"It is a beautiful home with a ton of space (we only had 3 people, but it easily sleeps 6), very clean and well-kept. Our hosts provided everything we needed to make our stay perfect. I also like that the hosts were not overboard with all the rules, as with some other rentals. The hosts were beyond friendly and had excellent communication throughout the whole process. If you are looking for a lovely home with a ton of space to stay while exploring Vermont and Massachusetts, I highly recommend...
The Jelly Mill-A River Retreat

Cozy Falls Brook Cabin: Hike & Swim On-Site!

10.0 out of 10, Exceptional, (10)
"The cabin is immaculate and very cute and cozy. It's lovely to be right by the brook in a quiet neighborhood set in a woodsy area. Lots of great places a short right away too. Brattleboro is lots of fun, and we loved hiking in the Manitou Project."
Cozy Falls Brook Cabin: Hike & Swim On-Site!

Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!

10.0 out of 10, Exceptional, (12)
"Love this property. We had everything we needed and then some. wasn't exactly sure as to where to put the trash as I don't have email on my phone , therefore I didn't receive the email about the trash and laundry until I got back home. I would rather have been able to text but everything worked out for us, and we had a wonderful, relaxing time."
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is AU$747
includes taxes & fees
1 Jan - 2 Jan 2025
Long Trail House at Stratton Mountain Resort

Dog-friendly chalet cabin with valley view, deck, and private hot tub

7.6 out of 10, Good, (19)
"Absolutely loved my stay at this tiny getaway house! The space was cozy, well-designed, and had everything I needed for a relaxing escape. The peaceful surroundings and thoughtful touches made it truly special. Perfect for unplugging and recharging. Can’t wait to come back for another retreat!" "
Dog-friendly chalet cabin with valley view, deck, and private hot tub

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (151)
"Never could get the wifi to work. I entered the code on the router 6 times but no luck. Would be helpful if you changed the password for the wifi to an easily entered name. The man who came to shovel unfortunately after we were stuck in the snow was very helpful and very nice.. He got us out."
The price is AU$596
includes taxes & fees
27 Jan - 28 Jan 2025
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

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

8.8 out of 10, Excellent, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

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

9.4 out of 10, Exceptional, (19)
"My husband and I decided to rent out this property for our reception and could not have been more pleased. The property was perfect for our intimate wedding. It was rustic, quiet, and had a ton of fun activities. The entire home was full of character and each room was unique. The two houses on the property were clean and taken care of, just older so do not expect modern and new. I personally love older rustic locations, especially ones that you know have been lived in and loved. I gave the...
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

9.6 out of 10, Exceptional, (9)
"We had a great time staying in Ashley’s condo! It was clean and well kept and super close to the village and slopes. I will definitely be back soon :)"
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

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

8.8 out of 10, Excellent, (42)
"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!

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

8.6 out of 10, Excellent, (20)
"Wonderful stay. Thanks again"
The price is AU$911
includes taxes & fees
12 Jan - 13 Jan 2025
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

8.6 out of 10, Excellent, (21)
"Good Condo in a great location"
The price is AU$560
includes taxes & fees
9 Jan - 10 Jan 2025
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Walk to Mount Snow, Cozy, Clean and Comfortable!

9.6 out of 10, Exceptional, (30)
"Cozy 1 bdrm very close to the slopes. The host are vey cooperative abd get back to you quickly."
Walk to Mount Snow, Cozy, Clean and Comfortable!

Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton

9.8 out of 10, Exceptional, (30)
"One of the best experiences I’ve had. Communication before we arrived was as expected, and everything was better than the pictures reviews and descriptions."
The price is AU$2,677
includes taxes & fees
20 Jan - 21 Jan 2025
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton

Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.

10.0 out of 10, Exceptional, (39)
"This property was beautiful, clean, well maintained, had everything we needed. Wish we could have stayed longer! Thank you for a weekend we’ll never forget! We hope to rent this house again in the future. "
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.

Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi

10.0 out of 10, Exceptional, (31)
"This trip was just as wonderful as the first. Spent our second Thanksgiving in this beautiful and private setting. It snowed 13 inches on TG day and it was so gorgeous! Sitting in the hot tub with the snow falling was really perfect. Everything was provided and check in and checkout were easy. Located close to Manchester, we had fun trying out hand at glass blowing at Hot Glass..too fun! Would recommend this place to all."
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

10.0 out of 10, Exceptional, (40)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Bear Creek Cabin

9.8 out of 10, Exceptional, (22)
"It was beautiful to wake up the first morning to see freshly fallen snow! Easy to get to, lots for the kids to do, wonderful place to share with my family for Thanksgiving! Only thing that I would change is having wood in the wood holder by the stove so that we didn’t have to carry it in. Would recommend to others. "
The price is AU$965
includes taxes & fees
29 Dec - 30 Dec
Bear Creek Cabin

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

9.8 out of 10, Exceptional, (41)
"This property is stunning. It fit our group of 14 perfectly. There are so many unique details and beautiful furniture. The kitchen was well-stocked for pots/pans/utensils/cleaning supplies which I always appreciate - makes group meals so much easier to manage. Quiet area, would be great all year round depending on what activities you like. Hot tub was a major highlight!"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

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

9.6 out of 10, Exceptional, (127)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
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

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1001)
"Like size of room"
The price is AU$156
includes taxes & fees
9 Jan - 10 Jan 2025
Colonial Motel And Spa

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (1000)
"Room with 2 queens was very spacious. "
The price is AU$164
includes taxes & fees
12 Jan - 13 Jan 2025
Hampton Inn Brattleboro

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (542)
"This place is a gem for the price and convenience to I-91. We got very lucky to find it. There’s a lovely restaurant just across the parking lot, a warm and clean pool, hot soup, hot chocolate, and coffee in the reception area and excellent hospitality. "
The price is AU$182
includes taxes & fees
26 Jan - 27 Jan 2025
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 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 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 17 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 Brattleboro Museum & Art Center and The Stone Church. Other places in town to visit include Latchis Theatre 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.