Search Holiday Rentals in Winhall

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May 15 - May 16
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May 16 - May 17
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May 17 - May 19
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May 24 - May 26

Top Holiday Rentals in Winhall

Exterior
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (177)
"We stayed the weekend for our 26th anniversary and had a wonderful time. Very private and everything was as described. The cottage is super charming! Will definitely be going back!"
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Fridge, microwave, oven, stovetop
Beautiful Manchester VT Mountain Retreat w/Hot Tub
10.0 out of 10, Exceptional, (22)
"Beautiful home, very clean, great hosts"
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Property grounds
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
9.8 out of 10, Exceptional, (57)
"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.
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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.
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
Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (174)
"It was very clean and area is beautiful. The pictures did not show inside stairs and i just had back surgery. It was very difficult for me on stairs. I wish i knew that before booking.. Also the couch in living room was terrible to sit in. If they remodeled the upstairs, i would stay again. Thank you"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Fridge, microwave, oven, stovetop
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (30)
"Two families stayed for a ski trip to okemo. Proximity to the mountain was a big plus for us. The cabin is cozy."
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
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
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.2 out of 10, Wonderful, (23)
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & 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
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, (68)
"Amazing! Cannot get a better location! So close to everything! Quick walk to village shops and slopes. Very clean. Lots more room than I was expecting for two big 17 year old boys and parents. Kids had their own bedroom, bathroom and storage area on main floor, adult had master suite with own bathroom upstairs. Plenty of room in kitchen and family room. The only complaint is that hotels hot tubs and pool were over run with too many little kids. "
The price is £295
includes taxes & fees
19 May - 20 May
Long Trail House at Stratton Mountain Resort
Exterior
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
10.0 out of 10, Exceptional, (143)
"Beautiful/nicely appointed home. The house had everything in it to make for a very comfortable stay and the hosts were so gracious, helpful, and communicative. We didn't want to leave and already can't wait to make a return trip! Thanks, Angelo and Deb!"
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
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
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 £291
includes taxes & fees
16 May - 17 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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
Fridge, microwave, oven, stovetop
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
9.8 out of 10, Exceptional, (15)
"Great location to restaurant and ski mountain"
The price is £234
includes taxes & fees
19 May - 20 May
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Property grounds
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (141)
"Ursula was super helpful and the location is very charming. Perfect spot for us!"
The price is £416
includes taxes & fees
1 Jun - 2 Jun
Idyllic Lakefront House Suited Two Families
Property grounds
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (183)
"The barn was spacious and had everything we needed. The property is breathtaking, great location to the town, and Jeff was a great host. Our dogs were welcome, living their best life running around the property, and it was so special to see the mountains and just breathe in the air there. Would love to come back in the warmer weather!"
The price is £639
includes taxes & fees
20 May - 21 May
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Property grounds
Vermont Treehouse compound: no cleaning fee. Spend a few days In the Trees
10.0 out of 10, Exceptional, (64)
"Wonderful property to rest and relax in nature. This was our second year staying at Rik's magical treehouse and we will continue to do so. Rik is a fantastic host and we feel blessed that he shares it with others."
Vermont Treehouse compound: no cleaning fee. Spend a few days In the Trees
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
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

Exterior
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (177)
"We stayed the weekend for our 26th anniversary and had a wonderful time. Very private and everything was as described. The cottage is super charming! Will definitely be going back!"
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Lounge
Bromley View Inn
3.5 star property
9.2 out of 10, Wonderful, (311)
"Nice family oriented motel "
Bromley View Inn
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 £234 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

The Manchester View

The Manchester View

5/5 Excellent
Tranquil and beautiful!
"It was cozy and charming! Great views and wonderful hospitality! "
A verified traveller stayed at The Manchester View
Posted 1 day ago
The Manchester View