Winhall Vacation Rentals

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USA > Vermont > Winhall

Make Winhall your next getaway—choose from 11 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, duplexes, and more


House rentals

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Winhall vacation rentals for every getaway

Dog-friendly Hot tub Internet
Alpine Duplex Unit 1 3D Tour
2 Bedroom | 1 Bath | Sleeps 4

Alpine Duplex Unit 1 - Winhall, VT

From $69
Winhall Wonder 3D Tour
3 Bedroom | 3 Bath | Sleeps 12

Winhall Wonder - Winhall, VT

From $162
Stratton High Meadow 3D Tour
4 Bedroom | 4 Bath | Sleeps 9

Stratton High Meadow - Winhall, VT

From $235
The Little Matterhorn 3D Tour
3 Bedroom | 2 Bath | Sleeps 9

The Little Matterhorn - Winhall, VT

From $175
Log Cabin Living 3D Tour
3 Bedroom | 2 Bath | Sleeps 12

Log Cabin Living - Winhall, VT

From $113

View 6 more homes

Recent Winhall vacation rental reviews

The space and layout were good, but the kitchen wasn't stocked w/essentials like enough cutlery, a cookie sheet, and (gasp!) there were no wine glasses. The mattress I slept on was terrible and there was a leak in the sink. There was one dish towel but it was dirty when we arrived (probably not the cleaners fault bc it was in the drawer) and when we went to use the wooden cutting board for a cheese plate, it had mold on it. Again, overall the setup and location were great. Working out some of these kinks would make it even better.
Karin S. | Mar 2022
We stayed 4 days and we loved the spaciousness of the house. The kids especially enjoyed hanging out in the finished basement, the adults enjoyed the firepit! I’d definitely stay there again!
Kevin S. | Mar 2022
Clean, comfortable and very conveniently located to all 3 ski areas and hiking trails.
Colin B. | Mar 2022

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!