Winhall vacation rentals
Vacation rentals in Winhall by owner — compare homes, condos and cabins, message verified hosts, and book direct with no service fees.
Winhall, Vermont is located near the popular Stratton Mountain Resort, surrounded by the scenic Green Mountain National Forest and the tranquil Gale Meadows Pond. Visitors flock to the area for skiing in winter, and hiking, mountain biking, and leaf-peeping in the warmer months. With Houfy, you can book directly with local hosts in Winhall, enhancing your vacation budget. From cozy ski chalets to pet-friendly cabins in neighboring Manchester and Londonderry, there's a home for every traveler. For nature aficionados, visiting during the fall foliage season offers spectacular views across the mountains.
Top-Rated Vacation Homes in Winhall
Browse the highest rated vacation properties in Winhall.
$1,847.55 USD total for 3 nights
Sep 28 – Oct 1, 2026
After putting vacations on hiatus for 2 years because of "you know what", I decided to enjoy a cool, relaxing summer break in the beautiful mountains of Vermont with friends. In the past, I've been to Vermont in the fall for the glorious foliage and I've skied at Stratton many times over the past 25 winter seasons. The Stratton Ski Resort is a luxurious, first class resort with over the top amenities and I always enjoy first class service whenever I visit this area, be it fall or winter. The hosts at this property, however, provide the ultimate, top of the line, experience, to their rental guests. David and Wanda's condo is beautiful - everything looks bright and airy and it is almost like you are stepping into a newly purchased space! The decor is beautifully appropriate, the condo is well appointed and comfortable and they are conveniently located on the ground floor of the complex, just steps from the communal firepit and a few hundred yards from the outdoor pool and hot tub. The space is outfitted with everything that you could ever ask for. David and Wanda are truly the most generous hosts I've ever encountered during any of my stays in Vermont. My friends and I loved absolutely everything about this rental and did not want to leave. I cannot say enough good things about this rental property. You should really rent it yourself and experience "the best of the best" for yourself. It is now #1 on my list. I have never stayed anywhere in Vermont, that is more beautiful or welcoming. After 25 years of rentals, that is saying a mouthful. Congrats to David and Wanda. They are doing everything right and I am so grateful that they shared their "little bit of paradise" with us and we were able to enjoy this over-the-top experience during our mini vacay.
$767.79 USD total for 3 nights
Sep 28 – Oct 1, 2026
Great property, everything you could need inside. Tons to do in the surrounding area and great places to eat. Property was amazing inside and out. Host was great kept in touch and informed. Hope we get a chance to stay here again.
$1,150.79 USD total for 3 nights
Sep 28 – Oct 1, 2026
Sierra’s place was beautiful, homey and clean. Was really 5 minutes from Stratton mountain which was perfect for us and our group. The house matched the photos accurately. She allowed us to check in early, and all instructions about the house were stated clearly. She also responded promptly when we had questions. This was the coziest house with all the best mountain vibes. Our entire group was obsessed with the house. We absolutely recommend her home. Will be back!!
$1,055.34 USD total for 3 nights
Sep 28 – Oct 1, 2026
We almost looked past this property simply because the cover photo was taken at winter time, and we stayed here in the summer. So glad we looked into it! The beds were all quite cozy, the baths recently renovated, the house smells like a wood cabin in the mountains- it was great! The basement where the ping pong table was located smelled quite musty, but to be expected in a basement. Also, the grill outside definitely needs to be replaced- so use with extreme caution as the entire bottom of it was burned through and non existent. We would love to stay here again in the winter time! The host was fantastic and quick to respond to all of our questions.
$881.18 USD total for 3 nights
Sep 28 – Oct 1, 2026
Great place! Exactly as described, proximity to lift is unbeatable. Sierra was extremely clear and easy to communicate with, and her home provided many important essentials (linens, brita filter—just to name a few). Will definitely look to stay here again!
$752.75 USD total for 3 nights
Sep 30 – Oct 3, 2026
We really enjoyed the unit and the location. The place was well equipped, very clean and everything worked well. Also, the communication with the owner was outstanding as she responded within a few minutes. We look forward to staying here again.
$902.00 USD total for 3 nights
Sep 28 – Oct 1, 2026
Perfect ski chalet getaway for our family including our pets. Everything was easy and as described, and the owners were responsive and friendly. The tiny Village of Winhall is nearby, and Manchester and Stratton and Bromley ski mountains are within 10-15 minutes. The house is cute and has nice towels, linens, and cozy blankets. The kitchen was clean and modern, and the house had amenities like the Nest and a car charger. Plus the owners left a yummy pancake mix welcome gift and creature comforts like plenty of tissue boxes, ski toe warmers and coffee. It is clear the owners care about their property and their guests' experience.
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Pet friendly vacation rentals in Winhall
Bring your furry friend along! Browse pet-welcoming homes in Winhall.
Why visit Winhall
Discover what makes Winhall a perfect vacation rental destination.
Skiing at Stratton Mountain
Prime skiing just 8 miles away
Stratton Mountain Resort offers world-class skiing and snowboarding just a 15-minute drive from Winhall, making it a top winter destination.
Explore the Green Mountains
Immerse in Vermont's natural beauty
The nearby Green Mountain National Forest offers hiking trails like the Lye Brook Falls Trail, located only 10 miles from Winhall.
Adventure in Jamaica State Park
Camping and kayaking nearby
Located 12 miles east of Winhall, Jamaica State Park provides outdoor activities like kayaking and camping along the West River.
Magic Mountain Fun Park
Family activities 10 miles away
Drive just 20 minutes to reach Magic Mountain, where families can enjoy various activities including a fun park and scenic chairlift rides.
Where to stay in Winhall
The best areas and neighborhoods for your vacation rental in Winhall.
Bondville
This quaint area is located near the Stratton Mountain base, offering easy access to skiing and local dining options. Ideal for ski enthusiasts.
Peru
Home to the scenic Hapgood Pond Recreation Area, Peru offers a peaceful retreat with lovely hikes and waterways.
Bromley Village
Perfect for ski-in/ski-out rentals, Bromley Village surrounds Bromley Mountain with well-maintained slopes and quiet, cozy accommodations.
Winhall Hollow
A rural area known for open spaces and picturesque views, it's ideal for those seeking a secluded getaway.
Find Winhall vacation rentals that suit your style
Vacation homes, condos, townhomes and more — pick the kind of Winhall vacation rental you want, then book it direct with the host.
Winhall vacation rentals with free WiFi, hot tub or air conditioning
Free WiFi, hot tub, air conditioning and more — every Winhall vacation rental here is listed by a verified host and bookable direct, with the price the host set.
Top attractions in Winhall
All within driving distance of Winhall vacation rentals.
Stratton Mountain Resort
A premier skiing destination with over 99 trails. · 8 miles
Lye Brook Falls Trail
A scenic 4.6-mile trail leading to Vermont's tallest waterfall. · 10 miles
Somerset Reservoir
Offers opportunities for fishing, kayaking, and photography. · 18 miles
Magic Mountain
Provides family-friendly skiing and snowboarding options. · 10 miles
Jamaica State Park
Features camping and river swimming along the West River. · 12 miles
Hapgood Pond Recreation Area
A serene spot for picnicking and swimming in the summer. · 15 miles
Getting to and around Winhall
Getting around Winhall Vermont is easiest by car, with nearby airports facilitating travel.
- ALBANY INTERNATIONAL AIRPORT
- Located 70 miles from Winhall, offering numerous national flights.
- HARTFORD-BRAINARD AIRPORT
- Regional airport around 100 miles from Winhall for private flights.
- CAR RENTAL
- Essential for exploring; rentals available in Manchester, 15 miles from Winhall.
- TAXI SERVICES
- Limited availability; consider planning taxi services in advance during peak season.
Similar vacation rentals near Winhall
Homes within 60 miles of Winhall, from verified hosts.
$6,582.00 USD total for 6 nights
Sep 28 – Oct 4, 2026
$2,294.20 USD total for 3 nights
Oct 5 – 8, 2026
$1,219.27 USD total for 3 nights
Sep 28 – Oct 1, 2026
$1,450.23 USD total for 3 nights
Sep 28 – Oct 1, 2026
$4,576.50 USD total for 3 nights
Sep 28 – Oct 1, 2026
$899.80 USD $809.08 USD total for 3 nights
Oct 26 – 29, 2026
$17,025.50 USD $14,593.18 USD total for 7 nights
Oct 4 – 11, 2026
$2,184.00 USD total for 3 nights
Dec 12 – 15, 2026
$1,919.00 USD total for 3 nights
Oct 12 – 15, 2026
$1,223.00 USD total for 3 nights
Oct 16 – 19, 2026
$1,107.00 USD total for 3 nights
Oct 5 – 8, 2026
Explore near Winhall
Cities and towns within driving distance of Winhall, each bookable direct with the host.
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More vacation rental destinations around Winhall
Frequently asked questions
Quick answers about booking vacation rentals in Winhall and what direct booking on Houfy actually means.
Vacation rentals in Winhall typically range from $150 to $450 per night, depending on location and amenities.
Yes, many rentals in Winhall are pet-friendly. Always check listings for specific pet policies before booking.
For skiing, Bondville and Bromley Village are ideal, offering proximity to Stratton and Bromley Mountains respectively.
The best time to visit Winhall is winter for skiing and summer for hiking and outdoor activities in the Green Mountains.
In Winhall, you'll find a variety of rentals including ski chalets, cabins, and family homes with nearby resort access.
Vacation rentals offer more space and an authentic experience, especially convenient for families and groups compared to limited hotel options.
Winhall provides unique access to Vermont’s pristine nature like fishing in the Deerfield River and exploring nearby historic sites.
Houfy is a direct booking platform where travelers book directly with property owners, avoiding commission-based service fees.
Yes, Houfy is a trusted platform for direct bookings, where guests communicate directly with verified property owners.

















































































































































