Winhall Vacation Rentals

Compare 24 vacation rentals.
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


House rentals

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View 4 Townhouses

Condo rentals

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Winhall vacation rentals for every getaway

Dog-friendly Hot tub Internet
Hit the Slopes!
3 Bedroom | 2 Bath | Sleeps 10

Hit the Slopes! - Winhall, VT

$331 avg / night
Runaway to Winhall
2 Bedroom | 1 Bath | Sleeps 5

Runaway to Winhall - Winhall, VT

$167 avg / night
Ski You Later
7 Bedroom | 7.5 Bath | Sleeps 16

Ski You Later - Winhall, VT

$596 avg / night
Wandering Creek Ski Chalet
1 Bedroom | 1 Bath | Sleeps 2

Wandering Creek Ski Chalet - Winhall, VT

$325 avg / night
Wandering Creek Ski Lodge
5 Bedroom | 3.5 Bath | Sleeps 12

Wandering Creek Ski Lodge - Winhall, VT

$999 avg / night

View 19 more homes

Recent Winhall vacation rental reviews

Highly recommend!! First things first, the home (which this is definitely a home, not a house) is beautiful with a fantastic view of Stratton Mountain. My wife and I and our friends spent the past weekend at the house and had a great weekend relaxing and enjoying the area. I spend all of Friday "working from home" up in the loft overlooking the snow on the trees and on Stratton through the large A-Frame window. The wifi was spotless, allowing me to talk all my meetings with video without issue. We decided to bring groceries and cook for most of our meals. The kitchen is very functional and had all the pots/pans/knives/etc. that we needed to make french onion soup, chili, scrambled eggs, etc. The massive kitchen island is the best to prepare food while everyone hangs around in the great room. We slept so well in the house. The beds are very comfortable (far preferred over my own bed at home!) and the home is so quiet and dark...perfect for sleeping. The night light was a nice touch to navigate to the bathroom or kitchen in the middle of the night for that midnight snack. The living spaces were wonderful. I'm a big sports fan and was able to watch my games on the tv in the warm basement, while my wife cuddled upstairs in the greatroom. The space was able to accommodate everything we wanted. Truly, the house was spotless. We were impressed with how well maintained all the bedrooms, bathrooms, and living spaces were. The Stratton area has everything you could need. The skiing is great (we did not ski this time around however), the food at the mountain is also great - we love the deli! There is awesome hiking in the area as well. If you love waterfalls, or peaks and view points All Trails has a ton of awesome trails to try. This weekend we did the Quarry Trail in Dorset which brought us through 4 different quarries on our way up to Owl's head peak. Manchester is also well within driving distance. For really good food, we would recommend taking the 25 minute drive in to Manchester and eat at any one of the delicious restaurants. Our advice would be to make reservations and to make reservations as early as possible...everything fills up so quickly! Quick plug for our favorite little bakery cafe - Dorset Bakery - about 20 minutes away. We absolutely loved our weekend and would highly recommend Aspen Lane Retreat!
Shawn F. | Feb 2024
This four bedroom house was perfect for our extended family of 6 adults and 2 kids. It's a short drive to Stratton and an even shorter drive to Bromley. We enjoyed skiing at both.
Kate R. | Feb 2024
Close to the mountain, beds were comfortable, plenty of room for the 11 of us
Timothy N. | Feb 2024
Winhall vacation rental FAQ

Yes, 36 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. 108 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!