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Top Holiday Rentals in Winhall

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Exterior
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (179)
"My husband and I loved this little cottage , we will definitely be back."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Fridge, microwave, oven, stovetop
Beautiful Manchester VT Mountain Retreat w/Hot Tub
10.0 out of 10, Exceptional, (23)
"Excellent house in a cute town. Went with a 5 friends - there was plenty of space for everyone to sleep and relax around the house. Very well maintained, very clean, and nice homey touches. Very easy to get in, and get everything to work (hot tub, sauna, etc). Felt like home away from home. Would definitely recommend!"
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
Fridge, microwave, oven, stovetop
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
9.6 out of 10, Exceptional, (44)
"We had a very nice stay. The house had plenty of room for our family including the living, dining, and sleeping areas. The location was great."
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
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Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
Exterior
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
10.0 out of 10, Exceptional, (48)
"My family and I had a great stay at the Skylight Lodge. It is very different from other rentals, being a former inn. There is plenty of space for a big group and the two master suites are great. The fireplace in the main room is like something out of game of thrones, and was the highlight of the trip for the adults. The kids spent most of the time playing games in the second living room on the first floor. The house is also very conveniently located near Manchester. We would definitely come...
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
Property grounds
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
9.8 out of 10, Exceptional, (58)
"We loved our stay at the lodge. We had two couples and kids ranging in age from 2 to 12. We did lots of skiing at Bromley but loved having Manchester so close to explore. The pinball arcade was a great rainy day activity for kids! The house was amazing and bigger than we imagined, we were all extremely comfortable. The only thing to mention is the stairs and upstairs loft are a bit scary for little ones. We blocked them with a baby gate and didn’t let the two year old up there, but it was fine...
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Fridge, microwave, oven, stovetop
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (30)
"My family really enjoyed this Lake House. The beautiful views of the lake were breathtaking. The house had everything we needed for preparing meals. The kitchen was functional and generally well equipped. The beds in the house were particularly comfortable. We enjoyed early morning coffee on the deck with perfect views of the lake. The location was great. Lots of wonderful hiking trials in close proximity. My only suggestion to the owners is to give the house a good deep cleaning. Nonetheless,...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, pool loungers
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (69)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is £264
includes taxes & fees
9 Jun - 10 Jun
Long Trail House at Stratton Mountain Resort
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
Exterior
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
9.8 out of 10, Exceptional, (157)
"The place is beautiful and the stay was fantastic. It is up a couple mile hill/road from the center of town, just long enough to make you feel you are out of the hustle. The property presents very well. The rooms are large for private space with 2 common rooms that are just as large for group time. The one suggestion would be to add a check in book of information, including necessary passwords (WIFI) and local attractions/restaurants. We had much of this in the interaction with the host through...
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
6 bedrooms, WiFi, bed sheets
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
9.6 out of 10, Exceptional, (69)
"This was our second stay at the condo. Can’t beat the convenience of ski in ski out and coming home for lunch. The owner, Ralph, is very quick at getting back with any questions. Highly recommend!"
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
Private and Artistic cabin, Pet friendly, no cleaning fee
Property grounds
Private and Artistic cabin, Pet friendly, no cleaning fee
10.0 out of 10, Exceptional, (244)
"We had a great stay at this cabin and the property. It's everything the write up says and then some. The owner is a true craftsman with an eye for creativity and for bringing the outside in. I wish I had taken a photo of my review that I left him handwritten in his leather bound book to share with you here. He has thought of everything to provide a peaceful, calm and tranquil getaway. There is so much wildlife to be seen and heard. The cabin is rustic and gave me Hobbit and fairytale vibes. We...
Private and Artistic cabin, Pet friendly, no cleaning fee
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Interior
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (47)
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (175)
"This was a great stay- thank you so much! The property was clean and serene, the house adorable and cozy and the hot tub is always a plus! It was a great area, we’ll have to visit again sometime :)"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Lake
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
10.0 out of 10, Exceptional, (116)
"Great place to stay for an early spring ski trip and eclipse viewing (we drove north after checking out). Clean, cozy place and pet friendly for our small dog. Located on a quiet dirt road but close to Ludlow town center and Okemo for skiing. Not too far from Killington either (which is where we went to ski). Minor issue for me was the bed was a bit too soft for my liking but otherwise, great place and would consider again in future."
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Idyllic Lakefront House Suited Two Families
Property grounds
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (142)
"Perfect family weekend ,! House clean & plenty of room for 5 adults & 1 child. Picture perfect, boating fishing, Crowley's cheese factory 10 minutes away. Definitely would love to return !"
Idyllic Lakefront House Suited Two Families
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (140)
"Great little house to enjoy spending time with family and all that VT has to offer. Wonderful host, we will be back."
The price is £287
includes taxes & fees
10 Jun - 11 Jun
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
TV, fireplace
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
9.2 out of 10, Wonderful, (15)
"Great location- 10-15min from Stratton, beautiful views, all the amenities. Awesome decor, will definitely be back!"
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
Exterior
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
10.0 out of 10, Exceptional, (145)
"Home was amazing. Met all our expectations. Highly recommend property!"
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Property grounds
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (185)
"Wonderful stay at a beautiful serene property. Highly recommended"
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Property grounds
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
9.8 out of 10, Exceptional, (187)
"We had a lovely stay, the kayaks and canoe were the feature of one afternoon and we greatly enjoyed paddling around Lake Pauline and checking out both dam areas. The house is very clean and well maintained, we fell in love with all the windows and light coming in the bedroom across from the bathroom. The quick walk to the sugar house was a feature for my kids, they also loved having the wii in their room and playing Mario kart with their aunt/uncle."
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
VT Cabin overlooking the West River and Village
Oven, stovetop, dishwasher, coffee/tea maker
VT Cabin overlooking the West River and Village
10.0 out of 10, Exceptional, (19)
"The cabin was perfect for a getaway! Felt secluded however walkable to small village, and within 20 minutes to Stratton. Perfectly stocked to stay in for meals!"
The price is £304
includes taxes & fees
10 Jun - 11 Jun
VT Cabin overlooking the West River and Village
Don't see what you're looking for?
See all available properties in Winhall
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.

Winhall Holiday Rental Travel Info

Popular accommodation
Winhall private holiday homes
Known landmarks
Stratton Mountain Golf Course
International airport
Albany, NY (ALB-Albany Intl.)

Other types of properties in Winhall you may be interested in

Bromley View Inn
Lounge
Bromley View Inn
3.5 star property
9.2 out of 10, Wonderful, (312)
"Its a nice adventure to experience how a new way to accomodate the clients by self-serve from checking in to checking out. The room is clean and comfortable."
Bromley View Inn
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Exterior
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (179)
"My husband and I loved this little cottage , we will definitely be back."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
Fridge, microwave, oven, stovetop
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
9.6 out of 10, Exceptional, (44)
"We had a very nice stay. The house had plenty of room for our family including the living, dining, and sleeping areas. The location was great."
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
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.

Everything you need to know about Winhall holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winhall holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winhall holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winhall holiday rentals we have selected for you start as low as £264 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 holiday 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 holiday.

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 holiday rentals in Winhall?

Yes, there are holiday rentals close to the most popular sights in Winhall, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Winhall?

Choose from 129 Expedia holiday rentals in Winhall for a memorable holiday.

What can I see and do in Winhall?

While exploring the area, visit family-friendly sights like Sugar Shack, or get outside and enjoy nature at Winhall River. Stratton Mountain Golf Course and Stratton Mountain Summit Gondola are a couple of places you'll find in the wider area.

What are holiday rentals like in Winhall?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winhall. Holiday rentals offer extras like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a small group gathering.

Recent reviews of Winhall properties
Expedia verified reviews

Toll Road Inn

Toll Road Inn

5/5 Excellent
"The hotel was so cute!! Very small hotel, very quiet and it was amazing that the windows in the rooms opened for fresh air. The backyard area, pool and hot tub were extremely clean. Very cute sitting area with games and books and a fireplace in the winter. Will absolutely be booking again in the future! "
A verified traveller stayed at Toll Road Inn
Posted 1 day ago
Toll Road Inn