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Brattleboro Vacation Rentals

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Dec 10 - Dec 11
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Dec 19 - Dec 21

Our top choices for Brattleboro vacation rentals

Exterior
The Jelly Mill-A Peaceful River Retreat

The Jelly Mill-A Peaceful River Retreat

Guilford
10.0 out of 10, Exceptional, (64)
"Beautiful rural location next to the Green River. A peaceful relaxing place to stay. We would love to stay here again "
United States
Georgene M.
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
$409 nightly
The price is $462
Dec 11 - Dec 12
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
3 bedrooms, desk, iron/ironing board, travel crib
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Dover
8.0 out of 10, Very Good, (2)
"Place was amazing! Beautiful property and so unique. Being pet friendly was a huge plus! We had a wonderful time!"
United States
Alexia R.
$450 nightly
The price is $509
Dec 14 - Dec 15
Total with taxes and fees
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
Property grounds
Owl's Nest Treehouse

Owl's Nest Treehouse

Alstead
10.0 out of 10, Exceptional, (13)
"Great place . Would highly recommend it.!"
United States
Peter G.
$310 nightly
The price is $336
Dec 14 - Dec 15
Total with taxes and fees
Owl's Nest Treehouse
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, (11)
"Beautiful new home, great for big family and friend groups. Comfortable bedding and furniture. Lots of open space and seating "
United States
Gena L.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
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, (48)
"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
Fridge, microwave, oven, stovetop
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

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

Dover
10.0 out of 10, Exceptional, (8)
"Nice in all respects,"
United States
Ken
$1,176 nightly
The price is $1,328
Dec 11 - Dec 12
Total with taxes and fees
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
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)
"I really enjoyed every aspect of my stay here and highly recommend the property. "
United States
Gregory G.
Cozy 2-bedroom cabin near Mount Snow 3 min drive
9 bedrooms, desk, iron/ironing board, free WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

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

Wardsboro
9.4 out of 10, Exceptional, (29)
"This place is enormous with nooks and crannies everywhere to get away, shoot pool, play video games, read, swim, sit in the sauna,barbecue, or wade in the brook below! Some of the rooms are great for a couple, others are better for a bunch of kids who are willing to sleep in a bunk or twin bed. "
United States
khs
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
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)
"House was perfect and just what we were looking for! Very clean, great hot tub, loved the fire pit!Cassie was incredibly helpful with local recommendations and going above and beyond!Highly recommend!"
United States
Neal T.
$757 nightly
The price is $855
Dec 17 - Dec 18
Total with taxes and fees
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
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)
"We had a wonderful stay."
United States
Joshua
$502 nightly
The price is $567
Dec 11 - Dec 12
Total with taxes and fees
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
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)
"My family and I loved our stay. This cabin had everything we needed and more. One thing we do wish we had was fans in the upstairs rooms, as we stayed in the summer time and it did get quite hot up there. The owners were very helpful, and amazing with communication. We would absolutely love to stay here again one day! "
United States
lizzie m.
Beautiful Lodging at Mount Snow with Hot Tub on Deck
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)
"Met family here and was a fantastic place for get together "
United States
Melissa C.
Beautiful Custom Built Timber Frame Home, Sleeps 11
Exterior
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Dover
9.4 out of 10, Exceptional, (16)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
$234 nightly
The price is $265
Dec 14 - Dec 15
Total with taxes and fees
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
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 is very clean, beautiful condo and scenery, owner was great and communication was incredible! Highly recommend, great stay!"
United States
Douglas D.
$451 nightly
The price is $510
Dec 11 - Dec 12
Total with taxes and fees
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, (43)
"We enjoyed our stay!!"
United States
Hillary S.
$536 nightly
The price is $599
Dec 11 - Dec 12
Total with taxes and fees
Bear Creek Cabin
Terrace/patio
LUX property, Stunning views, private setting,pet welcome, fire pit ,WIFI,AC,EV

LUX property, Stunning views, private setting,pet welcome, fire pit ,WIFI,AC,EV

Townshend
10.0 out of 10, Exceptional, (7)
LUX property, Stunning views, private setting,pet welcome, fire pit ,WIFI,AC,EV
Terrace/patio
Stratton South Long Trail Studio Adjacent to the Village and Lifts

Stratton South Long Trail Studio Adjacent to the Village and Lifts

Stratton
9.4 out of 10, Exceptional, (68)
"This studio apartment is cozy and comfortable, with a balcony offering great views. The kitchen is clean and functional, and indoor parking is very convenient."
United States
GO PIN
Stratton South Long Trail Studio Adjacent to the Village and Lifts
Fridge, microwave, oven, stovetop
Dog-friendly home w/ WiFi, private washer/dryer, and wood & electric fireplaces

Dog-friendly home w/ WiFi, private washer/dryer, and wood & electric fireplaces

West Dover
8.2 out of 10, Very Good, (10)
"Lovely place for a large group of people."
United States
Nicole M.
Dog-friendly home w/ WiFi, private washer/dryer, and wood & electric fireplaces
1 bedroom, WiFi, bed sheets
Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!

londonderry
10.0 out of 10, Exceptional, (2)
"We had a great stay. The cabin was well lit and perfect for two people. Very clean, warm, and comfortable. There was a snow storm the night before we left and they kept the driveway plowed for us. Gorgeous views and close to everything."
United States
Karen L.
$567 nightly
The price is $641
Dec 11 - Dec 12
Total with taxes and fees
Romantic Riverbed Treehouse - hot tub & new sauna!
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

Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"Cabin was strikingly pretty with the sustained Viking motif across the village and was very cosy even despite extreme cold weather. Christina the owner was very hospitable and welcoming. We stayed only one night but would definitely recommend and may return"
Brian 1-night trip
Posted 4 days ago
Vikings Villages Resort

Find out more about Brattleboro

Everything you need to know about Brattleboro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Brattleboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Brattleboro vacation 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 low season months. For more hustle and bustle, you may prefer to visit Brattleboro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $265 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Brattleboro rentals

At Expedia, we put the best Brattleboro vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Beautiful Custom Built Timber Frame Home, Sleeps 11: This vacation home rental outside of Brattleboro is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Brattleboro Museum & Art Center and The Stone Church. 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.