Winhall Vacation Rentals

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USA > Vermont > Winhall

Make Winhall your next getaway—choose from 25 great vacation rentals

There's just something about small-town living that melts away stress. Maybe it's the ambiance or the hospitality or the tranquility, but whatever the combination, Winhall, has it. With a population of fewer than 800 people, this town isn't just small and quaint: it is the epitome of peacefulness mixed with a tinge of adventure, perfect for your next New England vacation!

Explore Winhall house rentals, chalets, condo rentals, and more


House rentals

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View 2 Chalets

Condo rentals

View 2 Condo rentals

Winhall vacation rentals for every getaway

Dog-friendly Hot tub Internet
Winhall Wonder
3 Bedroom | 3 Bath | Sleeps 12

Winhall Wonder - Winhall, VT

$344 avg / night
Alpine Duplex Unit 1
2 Bedroom | 1 Bath | Sleeps 4

Alpine Duplex Unit 1 - Winhall, VT

$141 avg / night
The Burrow
5 Bedroom | 3 Bath | Sleeps 12

The Burrow - Winhall, VT

$280 avg / night
The Kresge Kabin
5 Bedroom | 4 Bath | Sleeps 18

The Kresge Kabin - Winhall, VT

$1,307 avg / night
Ralph's Chalet
3 Bedroom | 2 Bath | Sleeps 15 (12 Adults Max)

Ralph's Chalet - Winhall, VT

$388 avg / night

View 20 more homes

Recent Winhall vacation rental reviews

So comfortable for a large gathering. Plenty of space to cook, serve, hang out, play games, lounge and watch a fire. Comfortable beds. Owner's snow blower got us out of the driveway to catch early powder at Stratton.
Jeannine D. | Mar 2023
Nice view, cozy, everything you need
Art P. | Mar 2023
Great location. Nice condo. Clean and nicely decorated.
Claudia K. | Feb 2023
Winhall vacation rental FAQ

Yes, 30 of our Winhall homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 80 of our Winhall vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Winhall vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Winhall team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Winhall, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Where is Winhall, VT?

A part of Bennington County in southwestern Vermont, Winhall is located in the gorgeous Green Mountains, specifically at the foot of Stratton Mountain. In the western portion of the city, the crest of the Green Mountain range runs from north to south, offering a beautiful landscape and adventurous outdoor activities. The Winhall River also passes through Winhall at the point it cascades from the high range of the Green Mountains. All this is to say that Winhall offers the beauty and allure that you have come to expect from Vermont. 

Things to Do in Winhall, VT

Since Winhall is situated within the Green Mountain National Forest, exploring this area is convenient and oh so worth it! With three nationally designated trails, three alpine ski areas, seven Nordic ski areas, and about 900 miles of multi-use trails for hiking, cross-country skiing, snowmobiling, horseback riding, and bicycling, this forest is an outdoor enthusiast's dream. For those who don't particularly like these activities, photographing the forest's waterfalls and wildlife - including black bears, coyotes, beavers, and moose - might be more appealing. 

If you venture just eight miles out to Stratton Mountain Ski Resort, you can take part in all the activities the resort has to offer. In the winter, snowboard, ski, or snowmobile on the 3,875-foot Stratton Mountain. In the summer, play golf on a 27-hole layout or catch a free concert under the sun.  

Day Trips from Winhall, VT

If you're up for a day trip after spending a couple days hiking through Green Mountain National Forest, Woodstock is only 52 miles away. Known for its history and culture, this town offers several points of interest, such as the Marsh-Billings-Rockefeller National Historical Park, the Billings Farm and Museum, and several older covered bridges. 

For a quick trip, pack a few snacks and set the GPS for Ludlow. Only 27 miles away, this city features Okemo Mountain and its corresponding ski resort, the Okemo Mountain Resort. This resort was rated by Parents Magazine as the Top US Family Snow Resort, and it boasts 13 chairlifts and 121 trails. 

Get your small-town vacation on in one of our Winhall rentals and live it up (or relax it down) like a local. While some people may think of this area, and Vermont in general, as just winter destinations, Winhall is perfect year-round. Experience it for yourself by booking one of our vacation rentals today!