Holiday houses in Winhall
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Top-rated holiday rentals in Winhall
Guests agree: these stays are highly rated for location, cleanliness and more.
Home in Wilmington
5 out of 5 average rating, 8 reviewsLake & Mountain View Cabin - Sauna, Hot Tub, Hikes
Our family has been going to VT in the fall for 25+ years. The usual house we stay in was unavailable and lead us to find this home. Upon arrival we were stunned at the view, it is incredible in person! We had 5 adults and two children o this trip and this home offered us so much space and activities. My father even noted how everyone had their own space to dow whatever they wanted at any point in the day. We utilized the amenities every day and my kids were thrilled to have all the games to play inside as well as a beautiful lawn to run around and play on. Just a short drive down the driveway you reach the water which we also utilized mulitple times a day. Overall it was very peaceful and felt like a retreat and now my kids prefer this house over the old one! Definitely hoping to come back soon! Also, the hosts were very communicative and responsive before and during our stay, we very much enjoyed our time.
Home in Cavendish
5 out of 5 average rating, 40 reviewsOkemo <12 min Game room~Hot tub~Fire pit~Mtn Views
Julie was a wonderful host and her home is absolutely lovely! Plenty of great amenities to keep everyone happy and busy. Amazing family weekend getaway home! Thank you to Julie for sharing your home with us.
Apartment in Pownal
5 out of 5 average rating, 8 reviews"The Triple Chambers"
Place is going thru renovation so we got to our second floor apartment via steep and narrow stairs which could a problem for someone. Three spacious bedrooms and very clean and spacious bathroom. We absolutely loved the place.
Home in Hoosick Falls
4.91 out of 5 average rating, 11 reviewsEnjoy Fall & Experience Beautiful Changing Colors
Would highly recommend this beautiful spot!!! We loved the peaceful location and space for our entire family with the comforts of home in each room. Lots of extra pillows, towels, blankets, etc. fully stocked kitchen too. My kids wanted to stay longer, they had a great time. We will certainly come back!!
Home in Poultney
4.89 out of 5 average rating, 9 reviewsSnowberry Farm Home Sweet Home
We enjoyed our stay at Valerie’s. The house was spacious and comfortable. Loved the peaceful location. Thank you!
Apartment in Wilmington
4.91 out of 5 average rating, 129 reviewsGlobetrotter Retreat too - Minutes to the Mountain
This is our second stay at this location (different apartment in same building) and it was very centrally located and close to Mount Snow. This is a great place to stay in Wilmington.
Cottage in Fair Haven
4.92 out of 5 average rating, 151 reviewsHistoric Cottage 2 Bedroom 2 Bath Fast Wifi
Our stay was pleasant, and the space was very clean and cozy. Great deal for the price. Excellent communication and instructions and if I find myself back in the area I'd gladly book with Craig again!
Villa in Pownal
4.94 out of 5 average rating, 66 reviewsVermont Vacation Villa—Grapevine Getaway
A GREAT stay! We had a family weekend away here, the place was big enough to fit all of us with plenty of space. There is a TON of space in this home with large rooms! The great room has a beautiful view of the scenery, kitchen is well stocked with the essentials, and garage was great to keep ski gear in while we were not at the mountain. Would highly recommend staying here and our family would love to return!
Condo in Stratton
5 out of 5 average rating, 12 reviewsTop Flr Duplex 3BR 4BA - Walk to All @ Stratton Mt
A great spot. Very comfortable. Exactly as described in the listing. Easily accessible to the base by either a 10-15 minute walk or a frequent shuttle that leaves from the garage in the building. Very clean. Well appointed kitchen (we cooked all our meals in). Very helpful building staff. Would definitely stay again.
Home in Readsboro
4.86 out of 5 average rating, 125 reviewsDecember in Peaceful Vermont (Pet Friendly)
This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.
Home in Wilmington
5 out of 5 average rating, 25 reviewsKiki's Mountain Chateau
Had a weekend stay here and couldn’t have asked for a better place. Biggest thing is make sure you have AWD/4WD as the roads around are dirt roads and very snowy. My jeep however loved it. Very convenient commute to Mount Snow.
Apartment in Williamstown
5 out of 5 average rating, 118 reviewsDowntown | Waterfront | Walk to Shops
I had an excellent time staying in Williams’ place. It was easy to find easy to get into and very convenient. Would highly recommend.
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Other great holiday rentals in Winhall
Home in Wilmington
5 out of 5 average rating, 10 reviewsCountryside SKI Retreat - Indr Pool&HotTubGameRoom
This was a great place for a family get away. Right in the middle of Southern VT ski country. Easy to get to both the Mount Snow area and downtown Wilmington. Club house at Chimney Hill was awesome. We utilized the fitness center each day and there were plenty of people enjoying the indoor pool. We also had a chance to do some ice skating. The house had plenty of room and we had a great time just gathering near the fireplace and watching the snow fall. Shannon and Erika were great hosts and let us know what to expect every step of the way. We look forward to returning to the area and making more memories with our family.
Condo in Dover
5 out of 5 average rating, 10 reviewsCozy condo with direct mountain views and shuttle
This is a great place to stay with family to ski at Mount Snow. The Moover bus is just out the door (runs a bit faster then every 20 minutes). Two nice bed rooms and bathrooms. Nice living room and kitchen and great view. Already booked to go back!
Townhouse in Winhall
4.96 out of 5 average rating, 23 reviewsNew! Vermont Getaway! Stratton - close to skiing!
Conveniently located in the center of beautiful, forested mountains, this condo was easy, cozy and comfortable. We stayed for a fall weekend and enjoyed ourselves so much. Anthony was very communicative. We can’t wait to visit again!
Home in Monroe
4.92 out of 5 average rating, 13 reviewsThe Camp
We enjoyed a short ski trip to Berkshire East. M's place was comfortable, spacious and clean. The kitchen had everything we needed to cook and make coffee. They even had dog bowls and treats for our pup! Snow removal was completed early, allowing us to get out and on the slopes for the day. As M says in the description, you definitely need a vehicle with AWD or 4X4 since you are nestled in the mountains. We enjoyed the bountiful binder with history of the small town and local attractions. I would caution people with young children and older folks about the steep staircase to the 2nd floor where the bedrooms are. The 1 full bath is on the first floor so if you're like me, you need to navigate the stairs in the middle of the night. We didn't mind this since it is part of the charm of a historic building and our family of four including two teens had no problems. We enjoyed our stay and would love to return!
Home in Manchester
4.85 out of 5 average rating, 34 reviewsYour VT Ski House: Fireplace, Indoor Pool, Dogs
melissa was very responsive and even sent help when we needed heater :) nice house for a family gathering, our group had a great time!!
Townhouse in West Dover
4.74 out of 5 average rating, 19 reviewsBeautiful 4 Bedroom Townhome Minutes from Mt Snow
Great place for 10 with nice surroundings and close to cafe, restaurants and brewery. Perfect 2 days trip place. Jacuzzi and sauna also good add ons to mention.
Home in Dover
4.88 out of 5 average rating, 66 reviewsLarge Mount Snow Ski House with Hot Tub
10/10 will be returning next year! The house is huge with so many beds. There’s so much to do in the house from the board games to the rec room downstairs to the hot tub. Great Airbnb very clean !
Home in Wilmington
4.87 out of 5 average rating, 101 reviewsMtSnow * Hot Tub * Pool * Air Hockey * PingPong * Darts * 16ppl
The place was amazing. It was what the pictures show plus much more. Me and 10 of my friends slept comfortably and had a great time. Many games, nice kitchen, clean rooms and bathrooms, and if you’re a winter lover, hope it snows because this yard is amazing. We went sledding like kids again it was great. Definitely recommend. Right near mt. Snow and town of Wilmington which has great food options. Overall, quite the memorable stay.
Quick stats about holiday rentals in Winhall
Total rentals
320 properties
Nightly prices starting at
$176 AUD before taxes and fees
Total number of reviews
7.5K reviews
Family-friendly rentals
270 properties are a good fit for families
Pet-friendly rentals
120 properties allow pets
Rentals with a pool
50 properties have a pool
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