Winhall Vacation Rentals

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USA > Vermont > Winhall

Make Winhall your next getaway

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, townhouses, condo rentals, and more

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House rentals

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Townhouses

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Condo rentals

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Popular amenities for Winhall vacation rentals

Popular
Dog-friendly Hot tub Internet
Vermont Ski House
4 Bedroom | 2.5 Bath | Sleeps 8

Vermont Ski House - Winhall, VT

$298 avg / night
5.0 (1)
Fox Chapel 26
4 Bedroom | 3.5 Bath | Sleeps 8

Fox Chapel 26 - Winhall, VT

$600 avg / night
5.0 (3)
Piper Ridge B15
4 Bedroom | 3 Bath | Sleeps 10

Piper Ridge B15 - Winhall, VT

$457 avg / night
4.33 (3)
Beaver Glen
4 Bedroom | 3 Bath | Sleeps 10

Beaver Glen - Winhall, VT

$316 avg / night
4.33 (6)
Piper Ridge G4
4 Bedroom | 4 Bath | Sleeps 8

Piper Ridge G4 - Winhall, VT

$577 avg / night
5.0 (1)

View 13 more homes

Recent Winhall guest reviews

In all it was a nice house. Clean and comfortable. A few issues I feel should be addressed for the house mgt company. - There was app. 5" of packed and unshoveled snow and ice that led to the front door that was required for entry into house. It was difficult to cross (especially in the dark). -The entry code was random for success. I called Vacasa and a nice young man tried to help by sending two new codes. Neither of which worked. Eventually, he gave me the code to the lockbox for use on the deck door (that also helped in that I didn't need to cross the snow/ice path again to the front door). -Overall the house was very clean. A couple of concerns were... upon arrival there was some leftover trash that remained under the bed of one of the back bedrooms. Also, the LR ceilings were very high and pretty, however, there were a lot of cobwebs on the high ceilings and the ceiling fan/light looked as though it had not been cleaned in a long time with a lot of dirt buildup on the lamp and blades. -A modern pod type coffee pot would be more convenient than an old percolator. Perhaps these seem nit-picky. I wasn't going to leave a review but I have received numerous emails from Vacasa (that I deleted) asking for a review. I got another today, so, be careful what you ask for. 😊 It was a lovely house, in a convenient area with a lot of room. It was comfortable and clean. We would probably rent again. But, as Vacasa asked, "See any room for improvement...We're always looking for ways to make things better."
Paul C. | Mar 2025
We loved our stay in 26 Fox Chapel. The place was fancy looking but very comfortable and spacious. It was closer than we thought it would be to the mountain, a real easy walk. Definitely will try to stay there again next year.
Ryan M. | Mar 2025
Big enough for our whole group of nine. Nicely stocked. Great stay
ann b. | Mar 2025
Winhall vacation rental FAQ

Yes, 35 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. 95 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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Winhall, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

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24/7 guest service
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Seamless check-in
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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!