Winhall Vacation Rentals

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USA > Vermont > Winhall

Make Winhall your next getaway—choose from 12 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 condo rentals, house rentals, duplexes, and more


Condo rentals

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House rentals

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View 2 Duplexes

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 $96
Green Mountain Sleepaway 3D Tour
2 Bedroom | 1 Bath | Sleeps 2

Green Mountain Sleepaway - Winhall, VT

From $65
Stratton High Meadow 3D Tour
4 Bedroom | 4 Bath | Sleeps 9

Stratton High Meadow - Winhall, VT

From $216
Winhall Hibernation 3D Tour
2 Bedroom | 1 Bath | Sleeps 6

Winhall Hibernation - Winhall, VT

From $94
Green Mountain Hideaway 3D Tour
3 Bedroom | 2 Bath | Sleeps 8

Green Mountain Hideaway - Winhall, VT

From $94

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Recent Winhall vacation rental reviews

The condo had everything we needed and waaaay more beds and space than two people and three dogs required. We’d love to come back and bring a whole collection of friends. The location was perfect, being close to Stratton Mountain but in a small cluster of condos in a well wooded area, not like the dense, big condo buildings right at the resort. The dishwasher and clothes washer/dryer were helpful. The Roku TV was a nice touch, making it easy to Netflix. It seemed like all the condos around us had dogs, so the dogs had conversations through the walls with each other, which reassured us that the neighbors were unlikely to be bothered by our dogs being occasionally barky. I was initially skeptical about renting a condo with white carpets to stay in with three dogs during the summer season of muddy paws. However, the carpets seemed to be fairly stain resistant. The condo wasn’t “quaint” or recently renovated, but it was very functional, comfortable, and met all of our needs.
Faye S. | Sep 2021
Near Manchester and great shopping and restaurants
Philip F. | Sep 2021
Nice getaway at a comfy duplex
MELISSA J. | Aug 2021

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!