Holiday Rentals in Winhall

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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, (180)
"The bedroom overlooks a stream. The bed is very comfortable, and a third person could sleep next to the queen bed on the day bed. The bathroom with the shower and jacuzzi, kitchen, and sitting areas are all fabulous—like out of a magazine. It's very private. The only downside was when it was dark, the road was hard to see. But if you have GPS, you turn when it says turn, and you're fine. It's right off the main road, so it's very convenient. The property manager answered right away when I...
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
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.
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
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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, (24)
"All was as advertised and clean and great communication with host Hot tub under the deck so we didn’t use it pool table great but in a tight space so hard to get all the needed shots but no big deal for fun games of pool Overall a great stay and a great place!"
Beautiful Manchester VT Mountain Retreat w/Hot Tub
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, (32)
"Lovely property and great location to outdoor activities."
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (70)
"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 €390
includes taxes & fees
1 Jul - 2 Jul
Long Trail House at Stratton Mountain Resort
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (178)
"There was an issue at our check in that was quickly resolved and we enjoyed our stay a lot. Quiet, relaxing, and the area has some great restaurants. We stayed for our anniversary and will definitely will return."
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (26)
"Very cozy little house, close to everything, great hikes, and downtown was very cute!"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cabin in So. Vt enjoy the Mtns.
Exterior
Cabin in So. Vt enjoy the Mtns.
10.0 out of 10, Exceptional, (98)
"Great little cabin tucked in the countryside, very clean and had everything we could possibly need the owners were fantastic. I would highly recommend a stay here!"
Cabin in So. Vt enjoy the Mtns.
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
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Air Conditioning
Exterior
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Air Conditioning
9.8 out of 10, Exceptional, (158)
"Spacious nice cabin. Exactly as listed. Clean, everything worked and we had everything we needed. There were 12 of us, it rained all weekend and we had plenty of room to spread out or be together, as we wished. My only criticism would be that the screens need to be replaced and/or repaired. In really hot weather that we just had, it’s important to be able to open windows. Half or more of the screens were missing or had holes so could only use half of the windows to move air. Thank god it wasn’t...
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Air Conditioning
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, (141)
"The property was very peaceful and charming. Had everything we needed for our special time together. Location was close to good restaurants and MKT Grafton. Very glad we could take our cat!"
The price is €344
includes taxes & fees
1 Jul - 2 Jul
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
VT Cabin overlooking the West River and Village
Fridge, oven, stovetop, dishwasher
VT Cabin overlooking the West River and Village
10.0 out of 10, Exceptional, (20)
"Property was near our friends in Weston and close to everything in Londonderry. Has everything you need. Plan to stay again in the fall."
The price is €364
includes taxes & fees
28 Jun - 29 Jun
VT Cabin overlooking the West River and Village
Idyllic Lakefront House Suited Two Families
Property grounds
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (145)
"We had a relaxing week!"
Idyllic Lakefront House Suited Two Families
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Exterior
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
10.0 out of 10, Exceptional, (40)
"My husband and I wanted a relaxing few days to get away from our hectic lives. This small cabin was perfect, comfortable, and nicely appointed. Reading a book on the screened in porch with a cup of coffee was my favorite part. It is a quiet place in the woods but close to many small and quaint towns to visit in Vermont. The Newfane Store a few miles down the road was a great place to grab a coffee and meal. I also really appreciate that I could bring my dog. Many thanks for a warm and cozy...
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, (206)
"What an amazing place Lars shared with us for a few days. What a peaceful and fun place- very homey! We enjoyed watching the rabbits and the bear wandering the property from the spacious hot tub- great ways to enjoy any evening. Thanks again"
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
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, (147)
"Beautiful home and property with plenty of space for our extended family members to connect and yet have privacy for each couple as well. We will definitely return!"
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
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, (246)
"What a dream come true. This home is unlike any other and was truly the foundation for such a beautiful time shared with friends. Can’t wait to go back!"
Private and Artistic cabin, Pet friendly, no cleaning fee
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
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
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, (16)
"Great location to restaurant and ski mountain"
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
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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.

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, (180)
"The bedroom overlooks a stream. The bed is very comfortable, and a third person could sleep next to the queen bed on the day bed. The bathroom with the shower and jacuzzi, kitchen, and sitting areas are all fabulous—like out of a magazine. It's very private. The only downside was when it was dark, the road was hard to see. But if you have GPS, you turn when it says turn, and you're fine. It's right off the main road, so it's very convenient. The property manager answered right away when I...
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
The Equinox Golf Resort & Spa
Exterior
The Equinox Golf Resort & Spa
4.5 star property
7.4 out of 10, Good, (361)
"The Equinox is a charming historic hotel in a stunning Vermont setting. Although it's close to all the shops and restaurants in Manchester, it feels serene and quiet. We've stayed there several times and will continue to go back."
The price is €219
includes taxes & fees
28 Jul - 29 Jul
The Equinox Golf Resort & Spa
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 €344 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

Hampton Inn Bennington

Hampton Inn Bennington

5/5 Excellent
"Perfect place for what we needed. Clean, so comfortable. "
A verified traveller stayed at Hampton Inn Bennington
Posted 9 hours ago
Hampton Inn Bennington