
Vacation rentals in Winhall
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Top-rated vacation rentals in Winhall
Guests agree: these stays are highly rated for location, cleanliness, and more.

Stone Fence Cabin
Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Log Cabin, King Beds & AC Near Hike/Swim/Golf/Bike
Kick back and relax in this calm, stylish, newly built log cabin which was finished in early 2022. Fully equipped with stainless steel appliances, soapstone counters, central a/c, all new furniture, mattresses and bedding. First floor master bedroom leads into a large, covered, screened in porch, which is perfect for your early morning coffee or evening cocktails. Starlink high speed Wi-Fi and a smart tv in the living room and bedroom. 7 Minutes from Stratton Mtn, 15 from Mt Snow. Nearby lakes!

Riverbed Treehouse @hot tub & a new sauna & views!
The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

Summit View Ski and Golf Retreat w/hot tub & Sauna
Summit View Chalet @ Stratton is the ideal VT retreat, Minutes from Manchester, directly across the entrance from Stratton's 27 Hole Championship Golf Course. Beautifully remodeled! Relax in the hot tub on the deck with direct summit views in any season. Enjoy shuttle access to lifts, minutes from snowmobiling, hiking, fine dining and shopping. Comfortable accommodations for 6 adults and 5 children. Perfect for 2 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

Beautiful Timber Frame Retreat
This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Mountain view chalet with hot tub & fire pit!
Welcome to the Vermont View Chalet! This spacious, family-friendly property is perfect for year-round enjoyment. With the mountain view as your backdrop, come unplug by the fire pit and unwind in the hot tub. Perfectly situated between Manchester (shopping & dining) and Bromley/Stratton (skiing and entertainment). You're also just 2 minutes away from the Appalachian trail for the best hiking and fall foliage Southern Vermont has to offer. Look no further, you've arrived at your destination.

Modern Cabin with Hot Tub & EV Charging Station
Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Snow Valley Cabin-Cozy Escape Near Skiing & Nature
The Snow Valley Cabin is a three bed one-and-a-half bath chalet-style house designed for your perfect Vermont getaway. Wooden vaulted ceilings, wood-burning fireplace, beautiful view of the snow-capped Bromley mountain, and Scandinavian style details. We are conveniently located on the edge of the Green Mountain Forest just 4 miles from Bromley, 9 miles from Stratton, 14 miles from Magic, and 12 minutes to Manchester. Stay here to relax and wind down with friends and family, and even pets!

Inviting studio apartment above barn in Vermont
This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub
This historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 250 acre property.

Dog Friendly A-Frame Retreat near Hiking, Skiing
The Vermont A-Frame is a dog friendly cabin conveniently located on the edge of the Green Mountain Forest. WFH using our fast WiFi + enjoy nature while doing so! Whether your plan is to ski, shop, hike or just relax, the Vermont A-Frame is the ideal place to experience it all. With room for 4 and plenty of amenities, our charming A-Frame is sure to provide you with the perfect home for your Vermont vacation. Find us on social media! @thevermontaframe

LUXE Forest Retreat
Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.
Popular amenities for Winhall vacation rentals
Other great vacation rentals in Winhall

Charming Vermont Schoolhouse

Goldfinch Cottage: Timber Frame on 5 Private Acres

Highland Haus: stunning ski getaway with hot tub

Ski In/Out, Cozy 3BR Condo steps to Village

Spacious Chalet W/ Endless Entertainment THE BARN

The Nest at Bromley Knolls

Peakview Lodge: Hot Tub - Sauna - Fire Pit- Ski

Vermont Mirror House
When is the best time to visit Winhall?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $774 CAD | $806 CAD | $641 CAD | $482 CAD | $406 CAD | $392 CAD | $430 CAD | $438 CAD | $423 CAD | $462 CAD | $490 CAD | $680 CAD |
| Avg. temp | -5 °C | -4 °C | 1 °C | 8 °C | 14 °C | 18 °C | 21 °C | 20 °C | 16 °C | 9 °C | 4 °C | -2 °C |
Frequently Asked Questions
Are there Winhall vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 50 vacation homes with pools in Winhall, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Winhall have wifi?
Absolutely! We offer over 140 house rentals with wifi in Winhall. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Winhall?
Experience the best of Winhall with our apartment rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Winhall?
Winhall has more than 230 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Winhall have air conditioning?
Absolutely! We offer over 60 house rentals with air conditioning in Winhall. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Winhall?
Yes! Work meets play with ease at over 130 vacation rentals in Winhall featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Winhall have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Winhall. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Winhall have a kitchen?
Absolutely! We offer over 10 cabin rentals with a kitchen in Winhall. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Condo Rentals in Winhall?
Enhance your stay in our Condo Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with free parking, over 20 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Winhall?
Four-legged friends are welcome in Winhall. Choose from more than 100 vacation rentals for guests traveling with pets.
Quick stats about vacation rentals in Winhall

Total vacation rentals
Explore 270 vacation rentals in Winhall

Nightly prices starting at
Winhall vacation rentals start at $155 CAD per night before taxes and fees

Verified guest reviews
Over 7,670 verified reviews to help you choose

Family-friendly vacation rentals
230 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 100 rentals that welcome pets

Vacation rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wifi availability
270 of Winhall vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winhall rentals

4.8 Average rating
Winhall stays are highly rated by guests—averaging 4.8 out of 5!
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Saratoga Spa State Park
- West Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Pico Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Lake George Expedition Park
- Peebles Island State Park
- Dorset Field Club
- The Shattuck Golf Club
- Hooper Golf Course
- National Museum of Racing and Hall of Fame
- Northern Cross Vineyard
- Bromley Mountain Ski Resort




