
House holiday rentals in Winhall
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Top-rated house rentals in Winhall
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Popular amenities for house rentals in Winhall
House rentals with a pool

Hot Tub, Game Room, Minutes to Mt. Snow & Stratton
Whitley's place was just what we were looking for for our family weekend! Plenty of space with lots to do, the pool table was a big hit. Very close to Mount Snow and Stratton which was really convenient for the snowboarders/skiers in our group. Had a great time and would love to be back!

Magical Farm Getaway - a must visit!
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

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.

The Brick House on Washington Street
Great stay and was exactly what we needed for our entire family for a weekend wedding!

Idyllic Dorset Home: Serene Escape w/amazing views
My group of 9 had a wonderful stay here! The house was very spacious, clean, and modern and accurately represented in the posting. John was extremely responsive during our process and proactively checked in with us to ensure we were able to check-in to the property smoothly. We had a small issue with one of the stove top burners and when we reached out to John, he followed up immediately to resolve the issue. I highly recommend staying here!

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!! 🤩

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
Weekly house rentals

Charming Vermont Retreat
I felt fortunate to discover this rental. It was quiet, clean, and comfortable. We had a workshop near by and this provided a get away to rest between sessions. Catherine responded quickly to my questions. Looking forward to visiting again.

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.

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.

Stratton Shuttle, Hot tub, Sauna, 2 Suites 5 STARS
Fantastic stay at Christopher’s place. Great communication, hastle free booking experience.

Multi-Level Ski Retreat at Stratton Mountain
We had a wonderful stay Duojia’s residence! Peaceful location, clean, and the Stratton Mountain view was icing on the cake. There is privacy and so much space at this home. Thank you!

New 6-BR Luxury Home 6 Min from Stratton w/hot tub
I recently stayed at this Airbnb and absolutely loved it! The space was clean, cozy, and exactly as described in the listing. The host was incredibly responsive and made sure everything went smoothly from check-in to check-out. The location was perfect— very peaceful and relaxing. I highly recommend this place and would definitely stay here again!

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.

Ski Lodge Hideaway: 5 minutes to Stratton Mountain
We loved this house & our stay! It was everything we hoped for - cozy & comfortable. We used it for our Feb. ski trip to Stratton, only a few minutes away. We were not disappointed! Everything was just as described & pictured! I highly recommend this house! Thank you Sierra:)
Private house rentals

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!

Modern, Serene Farmhouse Retreat
This place was exactly what we needed to escape and unwind. So relaxing, cozy and comfortable.

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.

Home in the Heart of Dorset Village
Absolutely beautiful home inside and out. Very easy to find and within walking distance to the shops in Dorset. Plenty of private parking and easy access. We felt at home as soon as we walked in the front door. The entire home from kitchen, bathrooms and living areas were spotless and well stocked. We enjoyed all the light from the windows and the fantastic view of the pond out back. The bed and linens were superb. We were traveling with our two dogs and it was very convenient for them and we enjoyed their company during our travels. Our friends in nearby Manchester agreed that we found the "perfect" spot to stay in the area. Michael the host, was super friendly, communicative and helpful with his recommendations. Hands down our favorite Airbnb and are already trying to plan our next trip.

Antique Charm 8 Mins to Stratton 12 to Mt Snow
Great location, 10 min to Stratton, check in was super easy, Ryan was great to communicate with and very responsive. The house was wonderfully decorated and smelled fabulous when we first walked in, everything was clean and stocked. Great space for two small families.

Stratton 35 acres w/Hot Tub, VIP parking pass
I had the best time staying at Reid’s beautiful house. The grounds were beautiful and I had never stayed in an ABNB with so much room. The house itself was spotless, tons of room to host a group and equipped for cooking. Reid was extremely easy to deal with and made the trip memorable. Location wise it’s ~3min to get to Stratton base and honestly with the VIP parking pass you can be walking into the town from your within 5min of leaving the house. Would definitely stay here again

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.

Mountain View Getaway
We loved our stay at Nicole’s place. It was very peaceful and private- just what we needed! Our dog also felt right at home thanks to her welcoming touches. We would definitely stay there again!
Quick stats about house rentals in Winhall
Total rentals
170 properties
Nightly prices starting at
₹9,477 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
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- West Mountain Ski Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Lake George Expedition Park
- Dorset Field Club
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Autumn Mountain Winery
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Baker Hill Golf Club
- Pineridge Cross Country Ski Area