Holiday Rentals in West Brattleboro

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Our top choices for West Brattleboro holiday rentals

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.0 out of 10, Wonderful, (4)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is €180
includes taxes & fees
26 Dec - 27 Dec
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (46)
"Close to downtown, clean & comfortable!"
United States
Robbi C.
The price is €175
includes taxes & fees
24 Dec - 25 Dec
Lovely 2nd Floor Apartment

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - 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.
The price is €258
includes taxes & fees
5 Jan - 6 Jan 2026
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
Whitingham
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is €266
includes taxes & fees
23 Jan - 24 Jan 2026
Lake Whitingham & Mount Snow Area Village Apartment

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
Newfane
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is €221
includes taxes & fees
22 Jan - 23 Jan 2026
Wellness Getaway with a Personal Sauna, and Private River Beach!

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (58)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is €267
includes taxes & fees
5 Jan - 6 Jan 2026
Family Friendly Hilltop House In Putney Vermont

Downtown Hot Tub Escape

Downtown Hot Tub Escape
Keene
9.6 out of 10, Exceptional, (21)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
The price is €265
includes taxes & fees
12 Jan - 13 Jan 2026
Downtown Hot Tub Escape

Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.0 out of 10, Wonderful, (45)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
The price is €270
includes taxes & fees
21 Jan - 22 Jan 2026
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK

Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
2.0 star property
Jamaica
10.0 out of 10, Exceptional, (5)
"Great stay"
United States
Chelsea D.
The price is €197
includes taxes & fees
4 Jan - 5 Jan 2026
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is €242
includes taxes & fees
26 Dec - 27 Dec
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Couples 2 Bedroom Retreat-Close to Shelburne Falls

Couples 2 Bedroom Retreat-Close to Shelburne Falls
Colrain
10.0 out of 10, Exceptional, (4)
"This place was great! Even though it was raining we enjoyed the hot tub! It was super clean and comfortable. "
United States
KayKay S.
Couples 2 Bedroom Retreat-Close to Shelburne Falls

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.8 out of 10, Exceptional, (22)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Charming Home Walk to Downtown!

Charming Home Walk to Downtown!
Keene
10.0 out of 10, Exceptional, (2)
"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...
United States
Xilin J.
The price is €539
includes taxes & fees
6 Jan - 7 Jan 2026
Charming Home Walk to Downtown!

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (50)
"We had a very lovely stay. "
United States
mary c.
The price is €585
includes taxes & fees
6 Jan - 7 Jan 2026
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is €132
includes taxes & fees
6 Jan - 7 Jan 2026
2 Twin beds on 1st floor with En-suite bathroom.

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

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
The price is €401
includes taxes & fees
21 Jan - 22 Jan 2026
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

FaLL Western Mass Getaway-Airhockey-Firepit

FaLL Western Mass Getaway-Airhockey-Firepit
Colrain
9.8 out of 10, Exceptional, (38)
"Great house for family gatherings "
United Kingdom
John Paul B.
The price is €584
includes taxes & fees
19 Jan - 20 Jan 2026
FaLL Western Mass Getaway-Airhockey-Firepit

Wilmington Retreat Near Trails, Skiing & Festivals

Wilmington Retreat Near Trails, Skiing & Festivals
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveller
The price is €628
includes taxes & fees
28 Dec - 29 Dec
Wilmington Retreat Near Trails, Skiing & Festivals

Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
10.0 out of 10, Exceptional, (1)
"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."
United States
Grant D.
The price is €388
includes taxes & fees
19 Jan - 20 Jan 2026
Stunning Glass House nestled in the Vermont wilderness!

Mountain Chalet mins from Mt Snow Skiing/hiking

Mountain Chalet mins from Mt Snow Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is €423
includes taxes & fees
13 Jan - 14 Jan 2026
Mountain Chalet mins from Mt Snow Skiing/hiking
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 West Brattleboro Hotel Reviews

Find out more about West Brattleboro

Everything you need to know about West 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 West 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 West Brattleboro holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

West Brattleboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in West 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 West 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 West Brattleboro holiday rentals we have selected for you start as low as €258 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on West Brattleboro rentals

At Expedia, we put the best West 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 West 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 West 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 West 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

Can I find holiday rentals in West Brattleboro?

Yes, there are holiday rentals close to the most popular sights in West Brattleboro, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that West Brattleboro has to offer?

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. : This holiday home rental outside of West Brattleboro is located in the mountains, and has a fireplace, a patio and laundry facilities to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

What’s there to see and do in West Brattleboro?

While exploring the area, visit family-friendly sights like Brattleboro Bowl, or get outside and enjoy nature at Brattleboro Common. Other places in town to visit include Brattleboro Farmers' Market and Creamery Covered Bridge.

What’s a holiday rental in West Brattleboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in West Brattleboro. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family trips.