Photo by Shirley Rhodes

Brattleboro Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Brattleboro

Exterior
The Jelly Mill-A Peaceful River Retreat

The Jelly Mill-A Peaceful River Retreat

Guilford
10.0 out of 10, Exceptional, (64)
"Very clean, fitted with many amenities, three rooms we needed, attractive setting, near our family reunion. Easy booking and access to the property."
United States
Barbara S.
The Jelly Mill-A Peaceful River Retreat
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3.0 star property
Stratton
8.6 out of 10, Excellent, (77)
"Nice, clean room in prime location"
United States
Kristin
The price is ￥50,729
￥63,059 total
includes taxes & fees
Nov 23 - Nov 24
Long Trail House at Stratton Mountain Resort
Fridge, microwave, oven, stovetop
Cozy 2-bedroom cabin near Mount Snow 3 min drive

Cozy 2-bedroom cabin near Mount Snow 3 min drive

2.0 star property
Dover
9.6 out of 10, Exceptional, (9)
"Great cabin! Perfect for our family of 4 and our dog! Very close to mount snow and walking distance to great restaurants! "
United States
Lisa R.
Cozy 2-bedroom cabin near Mount Snow 3 min drive
Property grounds
Owl's Nest Treehouse

Owl's Nest Treehouse

Alstead
10.0 out of 10, Exceptional, (11)
"Great place . Would highly recommend it.!"
United States
Peter G.
The price is ￥42,523
￥52,347 total
includes taxes & fees
Nov 18 - Nov 19
Owl's Nest Treehouse
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton
9.6 out of 10, Exceptional, (166)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is ￥26,287
￥55,246 total
includes taxes & fees
Nov 17 - Nov 18
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Interior
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

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

Wilmington
10.0 out of 10, Exceptional, (227)
"Great house, fantastically well equipped (kayaks, bikes etc). Excellent, very responsive host. View out over the lake is amazing. Really enjoyed our stay. "
United Kingdom
Lucian L.
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Indoor pool, a heated pool
Seasons On Mount Snow - Ski-in/Ski-out

Seasons On Mount Snow - Ski-in/Ski-out

Dover
9.8 out of 10, Exceptional, (180)
"I would recommend this place. It was very enjoyable. Stay love the area and the staff at the swimming pool were very nice."
United States
Richard
Seasons On Mount Snow - Ski-in/Ski-out
Property grounds
Long Trail House Studio at Stratton Mountain Resort

Long Trail House Studio at Stratton Mountain Resort

Stratton
10.0 out of 10, Exceptional, (64)
"Our stay was incredible. The location was perfect, room and facility was clean. Thank you for being a great host, 10/10!"
United States
Tyler M.
Long Trail House Studio at Stratton Mountain Resort
Terrace/patio
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Townshend
10.0 out of 10, Exceptional, (5)
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
TV, fireplace
Lovely ski-in/out condo steps from ski lift with trails and amazing views

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

Stratton
8.4 out of 10, Very Good, (26)
"Great location close to lift. Condo is clean and well appointed."
United States
Grace Ann B.
The price is ￥10,979
￥43,037 total
includes taxes & fees
Nov 18 - Nov 19
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Outdoor spa tub
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Jamaica
9.6 out of 10, Exceptional, (21)
"Good spot for catching up with friends for the weekend. Hot tub was perfect and everything was comfortable."
United States
Ross P.
The price is ￥29,995
￥102,215 total
includes taxes & fees
Nov 18 - Nov 19
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Smart TV, fireplace, DVD player, table tennis
Beautiful Custom Built Timber Frame Home, Sleeps 11

Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington
10.0 out of 10, Exceptional, (108)
"The house is beautiful and has a gorgeous view, especially at night of the stars. Michael was super responsive with a couple of questions we had on logistics and supplies to bring. We would highly recommend staying there and will probably book again in the future."
United States
Jeff L.
Beautiful Custom Built Timber Frame Home, Sleeps 11
Fridge, microwave, oven, stovetop
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Dover
9.8 out of 10, Exceptional, (47)
"Overall a nice stay, thanks Jen!"
United States
Anonymous traveler
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
Property grounds
Beautiful Lodging at Mount Snow with Hot Tub on Deck

Beautiful Lodging at Mount Snow with Hot Tub on Deck

Wilmington
9.4 out of 10, Exceptional, (42)
"This cabin is geared more for Winter and skiing since there is no air conditioning. Our family of 5 guys stayed here on 7/25/2025 because it was not that far from our rafting location, hiking and other attractions in southern VT. The cabin is very clean and the kitchen is stocked for all one's needs. We spent several nights after dinner around the firepit. We very much enjoyed staying here."
United States
Richard D.
Beautiful Lodging at Mount Snow with Hot Tub on Deck
Smart TV, fireplace, foosball, table tennis
Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Windham
10.0 out of 10, Exceptional, (54)
"Consistently great time at this place (3rd time there)"
United States
Chad B.
Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Fridge, microwave, stovetop, dishwasher
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

Dover
9.6 out of 10, Exceptional, (5)
"Property was clean, well presented and very comfortable. We had a great time, checking out nearby waterfalls and history of such places as Bennington. We would stay again and recommend to friends and family.."
United States
Stephen T.
The price is ￥25,514
￥67,971 total
includes taxes & fees
Nov 16 - Nov 17
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Exterior
Bear Creek Cabin

Bear Creek Cabin

Charlemont
10.0 out of 10, Exceptional, (42)
"We enjoyed our stay!!"
United States
Hillary S.
The price is ￥61,852
￥93,098 total
includes taxes & fees
Nov 16 - Nov 17
Bear Creek Cabin
Interior
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

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

Dover
10.0 out of 10, Exceptional, (9)
"This place is somehow better than it looks online. It is truly spectacular. And incredibly easy ski in ski out. Ski in is right to the door and ski out is about 10 foot walk to the magic carpet in the backyard. Tina of room. First class appliances. Tons of parking. We had a big group. Also two great places to hang out upstairs in the great room then the kids needed up hanging out a lot on the main floor. Checking in was a piece of cake and Todd was very responsive if we needed anything. Can’t...
United States
Marc G.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Fridge, microwave, oven, stovetop
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

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

Townshend
10.0 out of 10, Exceptional, (61)
"Second time visiting this property during the winter with adults and kids (ages 6 - 11) and it was another great stay. Property owner easy to communicate with, beautiful land and home. Perfect location for our family get together."
United States
sarah m.
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Interior
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

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

Londonderry
8.6 out of 10, Excellent, (8)
"My husband and I stayed at the treehouse cabin for two nights. It was so adorable and had so many fun amenities from the hot tub, to the fire place and record player. They even had snow shoes for us to borrow and we were able to use them and had a fun morning snow shoeing. Easy check in, and just a nice clean fun place to stay."
United States
Meghan C.
The price is ￥50,796
￥87,630 total
includes taxes & fees
Nov 24 - Nov 25
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Brattleboro Hotel Reviews

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

10/10 Excellent
"Beautiful historic hotel. Loved the heated outdoor pool for an early morning swim. Good early morning coffee and delicious breakfast too. And they upgraded me to a suite! Couldn't be happier with my stay. "
Peter 1-night trip
Posted 4 days ago
The Porches Inn at Mass MoCA

Find out more about Brattleboro

Search for holiday rentals in Brattleboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Brattleboro using one of the methods below:

  • View our selection of featured holiday rentals in Brattleboro
  • Use the map to find apartments and other holiday homes in the Brattleboro neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Brattleboro while they last

Look no further and take a look at our great range of rental properties in Brattleboro!

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 Brattleboro Museum & Art Center. 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.