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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Winhall vacation rentals

A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

1. 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, (41 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
$587 nightly
The price is $659
Oct 21 - Oct 22
Total with taxes and fees
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

2. 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, (15 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
$794 nightly
The price is $897
Oct 26 - Oct 27
Total with taxes and fees
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A modern living room with a fireplace, a large sofa set, and a view through the glass doors.

3. 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.
$518 nightly
The price is $526
Nov 3 - Nov 4
Total with taxes and fees
New! Vermont Getaway! Stratton - close to skiing!
A modern two-story house with a front porch, a staircase, and a driveway.

4. 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, (30 reviews)
"House was perfect for a guys trip for skiing. Just as expected. Would stay again. "
United States
Michael A.
$847 nightly
The price is $957
Oct 14 - Oct 15
Total with taxes and fees
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
A room with a wooden coffee table, two white chairs, and a carpeted floor.

5. Mountain Retreat with Outdoor Living Space and Ping Pong Table in Vermont

Mountain Retreat with Outdoor Living Space and Ping Pong Table in Vermont
Winhall
10.0 out of 10, Exceptional, (1 review)
"Sierra was great to work with upon check in. We really enjoyed our stay."
United States
Jonathan W. B.
$503 nightly
The price is $569
Oct 21 - Oct 22
Total with taxes and fees
Mountain Retreat with Outdoor Living Space and Ping Pong Table in Vermont
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

6. Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (84 reviews)
"Nice place and great location!!!"
United States
William
$391 nightly
The price is $441
Oct 8 - Oct 9
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

7. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (36 reviews)
"Great space, great location!"
United States
Jason S.
$466 nightly
The price is $527
Oct 28 - Oct 29
Total with taxes and fees
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

8. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
$199 nightly
The price is $224
Oct 8 - Oct 9
Total with taxes and fees
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A playground with slides and climbing structures surrounded by trees.

9. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (21 reviews)
"Nice place "
United States
Janja L.
$336 nightly
The price is $380
Oct 8 - Oct 9
Total with taxes and fees
Cozy Bromley Retreat
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

10. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
$227 nightly
The price is $256
Oct 8 - Oct 9
Total with taxes and fees
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

11. Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
8.0 out of 10, Very good, (1 review)
$359 nightly
The price is $405
Oct 8 - Oct 9
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

12. Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very good, (36 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
$278 nightly
The price is $314
Oct 8 - Oct 9
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A living room with a television, sofa, and coffee table.

13. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (6 reviews)
"Very clean 2br 2ba condo in excellent location. Host provided detailed important information that helped us find property and how to access unit. I would definitely recommend staying here."
United States
Eileen R.
$407 nightly
The price is $460
Oct 14 - Oct 15
Total with taxes and fees
Long Trail House South Wing 2B2B Condo
A spacious living room with a stone fireplace, wooden beams, and a large sofa.

14. Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Londonderry
9.6 out of 10, Exceptional, (25 reviews)
"Super attentive and accommodating host! It was a perfect cozy getaway on a frigid weekend, and the fireplace and hot tub were just the ticket. "
United States
Meghan R.
$574 nightly
The price is $648
Nov 2 - Nov 3
Total with taxes and fees
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

15. Historic Home with Colonial Charm in Manchester

Historic Home with Colonial Charm in Manchester
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were absolutely amazing. We had a wonderful time. The home is beautiful. The host is very communicative."
United States
Victor G.
$392 nightly
The price is $443
Oct 27 - Oct 28
Total with taxes and fees
Historic Home with Colonial Charm in Manchester
An outdoor dining area with a wooden deck, a table set with plates, glasses, and a vase of flowers.

16. Tranquil Brookside Retreat with Hot Tub & Firepit

Tranquil Brookside Retreat with Hot Tub & Firepit
Peru
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful place. Comfortable and well furnished. "
United States
Michael B.
$621 nightly
The price is $696
Nov 1 - Nov 2
Total with taxes and fees
Tranquil Brookside Retreat with Hot Tub & Firepit
A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a view to the dining area.

17. Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
10.0 out of 10, Exceptional, (1 review)
"Communication with Caroline was top notch and speedy! Very clear instructions for accessing the property and check out. Even though this place is connected with two other rooms/units ( I think that is what it is) we never heard them and hopefully we didn't bother them either!The house was amazing inside and out. The location was exceptional!Thank you for a beautiful stay!"
United States
Eva G.
$412 nightly
The price is $465
Oct 27 - Oct 28
Total with taxes and fees
Modern Mountain Retreat w/ Chef’s Kitchen
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

18. Cozy 3 Bedroom Condo in the Heart of Manchester VT

Cozy 3 Bedroom Condo in the Heart of Manchester VT
Manchester
10.0 out of 10, Exceptional, (1 review)
"Beautiful place Very spacious and super organized we love our stay "
United States
Rafael
$556 nightly
The price is $565
Oct 13 - Oct 14
Total with taxes and fees
Cozy 3 Bedroom Condo in the Heart of Manchester VT
Property grounds

19. Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Stratton
$456 nightly
The price is $515
Nov 3 - Nov 4
Total with taxes and fees
Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
A cozy room with wooden walls, two green upholstered chairs with plaid cushions, a small round wooden table with a cup and a book, and a framed map of Vermont on the wall.

20. The MountainTop | Stratton & Mt Snow | Fire Pit

The MountainTop | Stratton & Mt Snow | Fire Pit
Stratton
10.0 out of 10, Exceptional, (10 reviews)
"Lovely place to stay. The stars truly are stunning. "
United States
Brenna G.
$486 nightly
The price is $582
Oct 12 - Oct 13
Total with taxes and fees
The MountainTop | Stratton & Mt Snow | Fire Pit
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

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

8/10 Good
"The room was VERY small, but it was clean and the bed was comfortable. There is not an attendant or any staff onsite. I had a bit of trouble getting the pet registration taken care of since I booked through a 3rd party. We asked for a 1st floor room since there's not an elevator. When we received our check-in information, we were given a room on the 2nd floor. If we only had to carry backpacks, it might have been fine. However, we had large cases, so it was difficult to drag them up the stairs. Also, if you are an above average size person, know that these rooms are small spaces. The bathroom is barely big enough to turn around in and the shower is tiny."
KERRY 1-night trip
Posted 8 hours ago
Hideaway Inn Mt. Snow

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 $148 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?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This vacation home rental near Winhall is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Winhall?

Choose from 93 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.