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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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.
The price is CA $279
CA $938 total
includes taxes & fees
Oct 19 - Oct 20
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.
The price is CA $460
CA $1,171 total
includes taxes & fees
Sep 29 - Sep 30
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A spacious kitchen with a large island, a stone fireplace, and wooden beams.

3. Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley

Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley
Winhall
10.0 out of 10, Exceptional, (13 reviews)
"House was great for our family ski trip! "
United States
Brooke S.
The price is CA $379
CA $978 total
includes taxes & fees
Oct 1 - Oct 2
Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley
A cabin with a triangular roof, a wooden deck, and a front porch.

4. The Vermont A-Frame Mountain Retreat

The Vermont A-Frame Mountain Retreat
Winhall
9.8 out of 10, Exceptional, (29 reviews)
"Great home, perfect weekend away at Stratton. Host was great and so was the property"
United States
Kevin M.
The Vermont A-Frame Mountain Retreat
A cabin with a wooden exterior, a chimney, and a snow-covered roof.

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.
The price is CA $627
CA $809 total
includes taxes & fees
Oct 19 - Oct 20
Mountain Retreat with Outdoor Living Space and Ping Pong Table in Vermont
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

6. 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
The price is CA $105
CA $364 total
includes taxes & fees
Sep 29 - Sep 30
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

7. 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
The price is CA $105
CA $316 total
includes taxes & fees
Sep 28 - Sep 29
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

8. 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.
The price is CA $105
CA $445 total
includes taxes & fees
Sep 27 - Sep 28
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

9. 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, (35 reviews)
"Great space, great location!"
United States
Jason S.
The price is CA $223
CA $642 total
includes taxes & fees
Sep 27 - Sep 28
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

10. 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
The price is CA $502
CA $624 total
includes taxes & fees
Sep 27 - Sep 28
Long Trail House at Stratton Mountain Resort
A playground with slides and climbing structures surrounded by trees.

11. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (20 reviews)
"Nice place "
United States
Janja L.
The price is CA $182
CA $529 total
includes taxes & fees
Sep 30 - Oct 1
Cozy Bromley Retreat
A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

12. 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)
The price is CA $197
CA $565 total
includes taxes & fees
Sep 27 - Sep 28
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
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, (5 reviews)
"Host was very accommodating and understanding. Really smooth communication with the host. And the location couldn’t have been much better."
United States
Ernesto M.
The price is CA $293
CA $678 total
includes taxes & fees
Oct 4 - Oct 5
Long Trail House South Wing 2B2B Condo
A rustic cabin with a hammock, wicker chairs, and a wooden deck surrounded by autumn foliage.

14. Cabin-Swim-Brook View-Woodfired Sauna-Firepit-Woodstove-7 min to Stratton-Dog OK

Cabin-Swim-Brook View-Woodfired Sauna-Firepit-Woodstove-7 min to Stratton-Dog OK
JAMAICA
10.0 out of 10, Exceptional, (1 review)
"Had a great couple days at the "glamping cabin." The ride to get there on a dark foggy night was a bit thrilling, but could immediately relax once I got into the cabin. Place has everything needed for a semi-primitive cabin experience. Enjoyed the sauna and thencozy bed. "
United States
Brittney C.
Cabin-Swim-Brook View-Woodfired Sauna-Firepit-Woodstove-7 min to Stratton-Dog OK
A spacious living room with a stone fireplace, wooden beams, and a large sofa.

15. 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, (24 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.
The price is CA $266
CA $786 total
includes taxes & fees
Sep 28 - Sep 29
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.

16. 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.
The price is CA $171
CA $586 total
includes taxes & fees
Sep 29 - Sep 30
Historic Home with Colonial Charm in Manchester
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.
The price is CA $247
CA $677 total
includes taxes & fees
Sep 30 - Oct 1
Modern Mountain Retreat w/ Chef’s Kitchen
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

18. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is CA $69
CA $423 total
includes taxes & fees
Sep 28 - Sep 29
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

19. ★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+

★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+
Stratton
9.8 out of 10, Exceptional, (66 reviews)
"Nice place, great location, helpful host!"
United States
Shanon L.
★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+
A spacious living room with a high ceiling, wooden beams, a large sofa, a dining table, and a view of the outdoors through large windows.

20. Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC

Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC
Jamaica
10.0 out of 10, Exceptional, (3 reviews)
"Great peaceful stay. Hosts were always in communication with us. Close to Stratton. Hot tube & sauna were a great top off to a day of skiing. "
United States
fran g.
The price is CA $320
CA $1,233 total
includes taxes & fees
Sep 29 - Sep 30
Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC
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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"The Dalmatian behind the front desk"
April 2-night trip
Posted 1 hour ago
Pointe at Castle Hill Resort

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winhall vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winhall vacation rentals we have selected for you start as low as CA $316 per night. Entering your travel dates in the search wizard 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 92 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.