Photo by Shirley Rhodes

Holiday Rentals in Brattleboro

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Holiday Rentals in Brattleboro

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

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (44)
"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 River Retreat

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 €496
includes taxes & fees
3 Mar - 4 Mar
Long Trail House at Stratton Mountain Resort

Stratton Mountain Resort Solstice Luxury 5 bedroom Ski-In/Out Vacation Home

9.8 out of 10, Exceptional, (49)
"Great location, ski in ski out, enjoyed the hot tub in the snow. Great for our group of 3 couples with young kids. Appreciated the well stocked kitchen. "
Stratton Mountain Resort Solstice Luxury 5 bedroom Ski-In/Out Vacation Home

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

10.0 out of 10, Exceptional, (43)
"right across from entrance and super convenient to town."
The price is €351
includes taxes & fees
19 Mar - 20 Mar
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

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

8.6 out of 10, Excellent, (24)
"The apartment was in a great location to get to the ski lifts. "
The price is €293
includes taxes & fees
27 Feb - 28 Feb
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

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

8.8 out of 10, Excellent, (22)
"Unit is very close to ski lift. Ski in / ski out was great!!!"
The price is €362
includes taxes & fees
3 Mar - 4 Mar
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym

7.0 out of 10, Good, (6)
"Dining shopping not too far, but not walkable. The amount we paid was more than double the advertised price, yet we were still asked to perform a laundry list of cleaning tasks before exiting the unit (vacuuming, folding blankets, emptying and taking out gargage, etc.). I realize there is likely a management fee, but most VRBO properties do not require anything more than making sure doors and windows are secure, sink is clear, thermostats set at certain temps, etc. The property is also in...
Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (113)
"Great place to stay with friends and family. Will be visiting again!"
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (152)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is €355
includes taxes & fees
24 Feb - 25 Feb
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

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

9.4 out of 10, Exceptional, (21)
"ideal for a large group of adult friends "
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

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

10.0 out of 10, Exceptional, (44)
"This house was so much fun! We had a large group of families with young children and there was plenty of space for everyone. The adults were able to hang upstairs in front of the fireplace while the kids were able to play downstairs in their own space. The additional house with game room was also a ton of fun! There were so many bedrooms as well!"
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

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!

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (51)
"This place was just about perfect with excellent hosts that were easy to communicate to. My only ask would be to get shades to block the sun in the morning in the bedroom to the left of the upstairs bathroom. We did not use that bedroom because of this reason. That being said, we loved this place so much that we already booked again for next year. "
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

7.0 out of 10, Good, (14)
"Great place. Clean and comfortable. Nicely stocked kitchen with newer appliances. Sauna was amazing. Had 10 inches of snow one morning and it was fully plowed by 7am!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Stratton Mtn Studio | Renovated | Walk to Lifts

10.0 out of 10, Exceptional, (26)
"Great location."
The price is €628
includes taxes & fees
3 Mar - 4 Mar
Stratton Mtn Studio | Renovated | Walk to Lifts

Cabin 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK

2.0 star property
10.0 out of 10, Exceptional, (1)
"Cabin was as advertised and very close to the mountain. Would definitely stay again "
The price is €248
includes taxes & fees
23 Feb - 24 Feb
Cabin 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK

Wilmington Vacation Rental Near Hiking and Skiing!

9.2 out of 10, Wonderful, (17)
"Perfect weekend house close to mt snow"
Wilmington Vacation Rental Near Hiking and Skiing!

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

10.0 out of 10, Exceptional, (213)
"Our annual family ski vacation is always at Mt Snow. This year we were lucky enough to spend a week at Tony and Jeanette’s home. Which is exactly as we felt - at home. The house is beautiful and the amenities perfect. The home was clean, guest linens and towels, paper goods all provided. We loved the view and the binoculars!! We would love to stay again. "
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Beautiful Lodging at Mount Snow with Hot Tub on Deck

9.2 out of 10, Wonderful, (40)
"Real Vermont feel. Pretty and nice quiet neighborhood!"
Beautiful Lodging at Mount Snow with Hot Tub on Deck
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.
Don't see what you're looking for?
See all available properties in Brattleboro
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Brattleboro you may be interested in

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (585)
"Property is very nice but walls are thin and there is a gazebo for smoking, outdoor grilling, and shooting off fireworks that is located on the grounds of the hotel. Lots of noise, was tough to sleep."
The price is €111
includes taxes & fees
3 Mar - 4 Mar
Comfort Inn & Suites Brattleboro I-91

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1005)
"All ok everything worked well just older decor "
The price is €114
includes taxes & fees
17 Feb - 18 Feb
Colonial Motel And Spa

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (1002)
"Staff was friendly and informative."
The price is €109
includes taxes & fees
17 Mar - 18 Mar
Hampton Inn Brattleboro
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?

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!: This holiday home rental outside of Brattleboro is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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 Brattleboro Museum & Art Center and The Stone Church. Other places in town to visit include Latchis Theatre and Brattleboro Farmers' Market.

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.