A calm lake surrounded by autumn-colored trees and a clear sky.

Winhall Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Winhall vacation rentals

Exterior detail

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (29 reviews)
"House was perfect for a guys trip for skiing. Just as expected. Would stay again. "
United States
Michael A.
$863 nightly
The price is $975
Jul 13 - Jul 14
Total with taxes and fees
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
TV, fireplace, books, music library

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Winhall
10.0 out of 10, Exceptional, (12 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
$851 nightly
The price is $962
Jul 2 - Jul 3
Total with taxes and fees
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Property grounds

3 Levels w/ Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit, ACs

3 Levels w/ Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit, ACs
Winhall
9.6 out of 10, Exceptional, (23 reviews)
"Very beautiful home with plenty of room for a big group! Easy drive to Stratton. Would definitely stay again!"
United States
Sarah S.
$757 nightly
The price is $856
Jul 2 - Jul 3
Total with taxes and fees
3 Levels w/ Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit, ACs
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.4 out of 10, Exceptional, (39 reviews)
"Our family had a wonderful time staying in this home."
United States
Meghan C.
$591 nightly
The price is $663
Jun 30 - Jul 1
Total with taxes and fees
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Exterior

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Jamaica
9.6 out of 10, Exceptional, (26 reviews)
"We enjoyed our stay at a great ski house that was in a good location to the mountain. Accommodations were comfortable for 6 adults and 4 kids and the shuffleboard, foosball and pool tables were a hit. "
United States
Jonathan H.
$735 nightly
The price is $831
Jun 30 - Jul 1
Total with taxes and fees
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Smart TV, fireplace

New! Vermont Getaway! Stratton - close to skiing!

New! Vermont Getaway! Stratton - close to skiing!
Winhall
10.0 out of 10, Exceptional, (1 review)
"The place was perfect for us! Easy stay. Very clean and the wood burning fireplace was great. Would def recommend!"
United States
Carolyn K.
$526 nightly
The price is $533
Jul 22 - Jul 23
Total with taxes and fees
New! Vermont Getaway! Stratton - close to skiing!
House (2 Bedrooms) | Interior

Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
Hiking Trails On-site: Cozy Falls Brook Cabin
Fridge, microwave, stovetop, coffee/tea maker

Hiking Trails On-Site: Cozy Falls Brook Cabin

Hiking Trails On-Site: Cozy Falls Brook Cabin
Dummerston
10.0 out of 10, Exceptional, (18 reviews)
"We had a great stay! Cabin is cozy and met all of our needs for the weekend. We loved exploring the nearby trails and shops. Our dogs loved it as well :) "
United States
Kelsey M.
Hiking Trails On-Site: Cozy Falls Brook Cabin
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (169 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
$324 nightly
The price is $363
Jul 8 - Jul 9
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
$902 nightly
The price is $1,010
Jul 6 - Jul 7
Total with taxes and fees
Cozy Vermont Cabin · Mountain Views · Near Okemo
Dining

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"We had a great stay! The house was clean, comfortable, and exactly as described. The location was perfect and the host was very responsive. We’d definitely stay here again and highly recommend it."
United States
Stephanie F.
$367 nightly
The price is $411
Jul 9 - Jul 10
Total with taxes and fees
Charming Chester Farmhouse near Near VT Slopes
Private kitchen

The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
$279 nightly
The price is $312
Jul 17 - Jul 18
Total with taxes and fees
The Studio with a View. Bring your dog, too!
Outdoor pool, a heated pool

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (23 reviews)
"Great location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
$479 nightly
The price is $536
Jun 30 - Jul 1
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
$182 nightly
The price is $206
Jun 30 - Jul 1
Total with taxes and fees
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (11 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$336 nightly
The price is $380
Jun 30 - Jul 1
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
Terrace/patio

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (46 reviews)
"The property was beautiful and it truly felt like an escape. I"
United States
Kristina M.
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
House (3 Bedrooms) | Interior

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Exterior

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
$512 nightly
The price is $573
Jul 14 - Jul 15
Total with taxes and fees
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
TV, fireplace, foosball, stereo

Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
$434 nightly
The price is $471
Jul 8 - Jul 9
Total with taxes and fees
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Property grounds

Dover Summer Specials-Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!

Dover Summer Specials-Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!
Dover
10.0 out of 10, Exceptional, (9 reviews)
"Awesome place, fantastic amenities and easy to get to. Looking forward to coming back."
United States
Connor S.
Dover Summer Specials-Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winhall Hotel Reviews

The White House Inn

The White House Inn

10/10 Excellent
"Beautiful property, fantastic staff"
Julie 1-night trip
Posted 2 hours ago
The White House Inn

Find out more about Winhall

Everything you need to know about Winhall vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winhall vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winhall vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winhall vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winhall. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winhall in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $312 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winhall rentals

At Expedia, we put the best Winhall vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winhall rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winhall vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winhall. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Winhall?

Yes, there are vacation rentals close to popular sights in Winhall, or you can choose a secluded option if you want a relaxing place to stay.

What's the top vacation rental that Winhall has to offer?

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews: This vacation home rental near Winhall is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Winhall?

Choose from 106 Expedia vacation rentals in Winhall for a memorable vacation.

What can I see and do in Winhall?

Green Mountain National Forest and Winhall River are a couple of lovely local spots to get outside and enjoy nature. Stratton Mountain Golf Course and Stratton Mountain Summit Gondola are a couple of places you'll find in the larger area.

What are vacation rentals like in Winhall?

Vacation rentals are private accommodations you can book for several days or longer in Winhall. Vacation rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great option for family trips or small group gatherings.