
House holiday rentals in Winhall
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House rentals with a pool

Magical Farm Getaway - a must visit!
We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!

The 1770 House
Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!

Adams Farm-"The Little Farmhouse"
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.

Historic Home on 17 acres of land. Go escape!
Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩

Spring Getaway @ Mt Snow! Hike, Bike, Sleeps 8.
We had such a great time staying here! The house was so cozy and clean and was perfect! Felt like being at home and not staying in an Airbnb. Super close to the mountain, especially if you park in carinthia! Loved the guest book that they have in the kitchen, a fun added touch! Robert was extremely responsive to any messages and super accommodating with us and our needs! Absolutely would recommend staying here!!

Wander In | Close to Mount Snow & Stratton
This place was a dream for families. We traveled with 4 children and an infant. The house was roomy for the whole crew to hang out and eat together. We loved how clean and organized it was. We enjoyed hours at the pool, which was a huge hit with the littles. VRM was very helpful with any questions that came up. The location was great for skiing at Mt. Snow. We wish we had stayed one more night but our infant became very sick and had to head back a day early. To be honest, the place is more beautiful in person than in the pictures and we feel so lucky to have been able to stay there. Big plus to have laundry on site. Kitchen has everything you need to cook all your meals.

Historic 1850’s Renovated Farmhouse w/ Pool!
9 adults and 3 children all met up for a family weekend! We came from NY, NH and Maine! The house was perfect! Plenty of room to gather or separate! Even tho it was a chilly rainy weekend the kids managed to get in plenty of pool time! Tanya was very responsive and Melvin was the greatest! Our first morning he came right over to fix a slow drain. Highly recommend!! Kim and family

Hollywood Bungalow in the Berkshires #C0191633410
Diana and family were amazing super friendly, accommodating and checked in on use through out. We arrived later than expected but Diana waited for us and showed us around the property. We even got to see her dogs, meet her family, met the horse on the property behind and great conversations with Diana. She made us feel right at home. She prepped the pool for us, left us some good snacks and offered lots of recommendations. When you visit check out the theater set up, it’s pretty cool with insane sound system and clear video. Comfortable beds and all around beautiful property. If you visit in the summer it is a little warm on the second floor but we cooled off in the pool and just made sure to turn the fans on. It was the perfect birthday trip, relaxing, private and homey. My family and I are already looking forward to the next trip. Thank you to Diana for everything and hope we can meet again! 100% recommend.
Weekly house rentals

Idlewoods
My friends and I had a wonderful time staying at Matt and Melissa’s beautiful Airbnb while attending a wedding in nearby Dorset. The location was perfect — secluded in the woods while still being easy to locate and close to shopping and dining in Manchester. I would HIGHLY recommend this property to anyone visiting the area!

Mountain House between Stratton, Bromley, Magic
This place is a gem! Large space but felt intimate and cozy. The fireplaces are great, the deck looked inviting but we had so much snow, we spent most of our time on the slopes. Amazing art work throughout, well stocked kitchen, and lots of light! Great space.

Magical Retreat Cottage - Waterfalls everywhere
Gene’s house is a place of peaceful quiet and beauty. It’s well appointed and comfortable, with wireless and all the various conveniences, but it’s far more than that. The separation between the interior and the beautiful meadow and forest outside dissolves through Gene’s use of windows and glass doors, and the calming sound of falling water can be heard in every room. His use of color and symmetry create an environment that allows you to decompress, and as a result, you can’t help but to connect with the beauty of the forest. The waterfalls are wonderful to sit by; it was too early in the season for a swim in a cold mountain stream, but that’s just me. The design and setting of the home is a reflection of Gene. If you visit, I recommend that you get to know him a bit. His kind attentiveness makes him a first-rate host, but it’s part and parcel of his uncommon connection to the world around him. Gene was more than a host to us- he became a true friend. We will be back.

Hilltop Hideaway: Stratton Views | Hot Tub | A/C
The house was great! Spacious with two living rooms and two fireplaces. Just minutes from Stratton mountain. We loved the hot tub and used the grill too. Check-in super easy and we had an issue on the last day and the host was very responsive.

Beautiful 3-4 BR, 2 Ba, Sleeps 9
Patrick’s place was all we needed for out family skiing weekend. Once coming from the mountain we were able to relax, play pool, listen to music, just relax. The house is so beautiful, we felt pretty much at home. Patrick took care of every detail to make it the perfect place to stay when in the area, easy to drive to Stratton Mountain. I will stay here again for sure.

The Vermont Hideaway
We had a terrific 2-night stay at Anthony's house in Winhall, just over the border from Manchester. The house is just off of Route 30, about a 5-6 minute drive from downtown Manchester. There was plenty of space for our family, with 4 separate bedrooms (2 on the main floor and 2 downstairs). The house is updated, the furniture is tasteful, and everything was very clean. We would recommend this to anyone looking for a nice place to stay for a weekend in the area.

Mountain View Getaway
My partner and I were craving a weekend getaway to unwind and escape our hectic schedules. Nicole’s place was the perfect fit! It was exactly as depicted in the listing - quiet, private, and with a breathtaking view of Mt Tabor. Manchester, VT, was just a short drive away, offering a delightful mix of shopping and dining options. This place exceeded our expectations and was exactly what we needed!

Vermont Mirror House
I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.
Private house rentals

Charming Vermont Retreat
Catherine’s place was perfect for our stay. It was so cute, nicely decorated, very clean, and convenient to everything. If we are ever needing a place to stay in Dorset we will definitely be back!

Lakefront gem
Our stay at the lake was truly amazing! The house was impeccably clean and well-maintained, and the location was perfect for enjoying the lake. Lisa was incredibly responsive and helpful throughout our stay. Highly recommended!

2-Bedroom Home, 7 Minutes From Stratton Mountain
Ariana’s place was great after a day of snowboarding at Stratton. Great location, the home was cozy and we had a great time relaxing at the house. Ariana was responsive to our question and the home was well equipped to enjoy a meal at home after being out all day.

The Little Matterhorn
We had a wonderful experience at The Little Matterhorn. The house was as described per the listing, clean, comfortable, and tidy. The communication provided by the host, Sierra, was fantastic - including local referrals prior to check in, assistance with check in / check out, and response times that were almost instant. Thank you for making our VT experience stress free!

The Post Haus: one-of-a-kind modern VT experience
Stayed at the Post Haus twice now. Loved it both times. The property and private location is perfect for our rescue dog and is beautiful with the cool river water rapids and unique sky watching experience at day and night.

The Village Cottage
Jason is incredibly accommodating. We've been visiting for two years now and absolutely love everything—the location, the easy access to town, and the place is so warm definitely a plus to have your own fireplace after ski the whole day. We can’t wait to come back!

Lye Brook Retreat - Manchester
A Truly Wonderful Stay at Sheila’s Home! Sheila’s home was warm, welcoming, and absolutely spotless. Every detail was thoughtfully prepared, from the cozy decor to the well-stocked kitchen and comfortable bed. It felt more like staying at a friend’s home than a rental. The neighborhood was peaceful & perfectly located, and Sheila was a kind and responsive host who truly went above and beyond. Her hospitality made all the difference. One of the best Airbnb experiences we’ve had—thank you, Sheila, for such a special stay!

Artist Forest Retreat
Really lovely cabin with beautiful open design and decor. Reasonable drive to Magic Mountain and the surrounding area for skiing and other winter sport activities, and a great bathtub for your sore muscles afterward. Heat was super effective, hot water didn't run out even with four of us showering back-to-back, kitchen was well-supplied and there's a nice big driveway with plenty of room to park and turn around. There was even a closet full of boardgames; we played a lot of Scrabble. Of note — like much of Vermont, this is on a gravel/dirt road and it would be a bit sketchy to get there without good tires and four wheel drive. It also snowed a couple times while we were there and the stairs up to the house get very icy. So generally, if you're going in winter, be prepared.
Quick stats about house rentals in Winhall
Total rentals
170 properties
Nightly prices starting at
$140 SGD before taxes and fees
Total number of reviews
3.8K reviews
Family-friendly rentals
160 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
80 properties have a dedicated workspace
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Six Flags Great Escape Lodge & Indoor Water park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- West Mountain Ski Resort
- Saratoga Spa State Park
- Pico Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Stratton Mountain Resort
- The Shattuck Golf Club
- Lake George Expedition Park
- Magic Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Mount Sugarloaf State Reservation
- Clarksburg State Park
- Pineridge Cross Country Ski Area
- Bretwood Golf Course
- Fox Run Golf Club
- Baker Hill Golf Club