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Holiday Rentals in Brattleboro

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Holiday Rentals in Brattleboro

The Jelly Mill-A Peaceful River Retreat

Guilford
10.0 out of 10, Exceptional, (63)
"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

Long Trail House at Stratton Mountain Resort

3.0 star property
Stratton
8.6 out of 10, Excellent, (76)
"Nice, clean room in prime location"
United States
Kristin
The price is €375
includes taxes & fees
11 Nov - 12 Nov
Long Trail House at Stratton Mountain Resort

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

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

Townshend
10.0 out of 10, Exceptional, (4)
"Had a great time . Excellent communication Very clean .Would definitely stay there again. "
United States
Chris R.
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

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 €301
includes taxes & fees
11 Nov - 12 Nov
Owl's Nest Treehouse

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 €315
includes taxes & fees
11 Nov - 12 Nov
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

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

Wilmington
10.0 out of 10, Exceptional, (226)
"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

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 €503
includes taxes & fees
17 Nov - 18 Nov
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

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

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

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.

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

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 €370
includes taxes & fees
11 Nov - 12 Nov
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

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

Stratton
8.4 out of 10, Very good, (26)
"Extremely nice 1 bedroom apt , close to tennis courts , gym and amazing hikes ."
United States
Jonathan P.
The price is €246
includes taxes & fees
11 Nov - 12 Nov
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!

West Dover Vermont
9.6 out of 10, Exceptional, (26)
"Perfect location to walk to slopes. The host was phenomenal! Very responsive and helpful. Can’t wait to stay again soon!"
United States
R B.
Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!

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

The Mountain Escape!

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 €523
includes taxes & fees
12 Nov - 13 Nov
The Mountain Escape!

Bear Creek Cabin

Charlemont
10.0 out of 10, Exceptional, (42)
"We enjoyed our stay!!"
United States
Hillary S.
The price is €533
includes taxes & fees
16 Nov - 17 Nov
Bear Creek Cabin

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

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Dover
10.0 out of 10, Exceptional, (7)
"Our family had such a great time. We absolutely loved the space. So much bigger than what we expected. Our kids loved the bunkbed room. Plenty of room for our friends. Love the hot tub on the back deck. The kids really enjoyed the pool at the amenity center. Todd was extremely responsive and we really had a great trip. Look forward to coming back next season."
United States
Michelle V.
The price is €756
includes taxes & fees
11 Nov - 12 Nov
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
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

Find out more about Brattleboro

Everything you need to know about Brattleboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Brattleboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Brattleboro holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Brattleboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Brattleboro. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Brattleboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Brattleboro holiday rentals we have selected for you start as low as €246 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Brattleboro rentals

At Expedia, we put the best Brattleboro holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Brattleboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Brattleboro holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Brattleboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 Peaceful 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 20 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 The Stone Church and Brattleboro Museum & Art Center. Other places in town to visit include Latchis Theatre and Vermont Marketplace.

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.