House vacation rentals in Winhall

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Popular amenities for Winhall house rentals

House rentals with a pool

Top guest favorite
The open living area features a spacious green sofa with decorative pillows, facing a rustic wooden coffee table. Natural light illuminates the space, highlighting the vaulted ceilings and a cozy, inviting atmosphere. A breakfast bar can be seen in the background along with the kitchen area.
Home in Wardsboro
5 out of 5 average rating, 58 reviews

Hot Tub, Game Room, Minutes to Mt. Snow & Stratton

ChloeRating, 5 stars2 months ago
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!
Guest favorite
The farmhouse features a classic two-story white exterior with green shutters and multiple windows. Snow covers the ground in front, while the entrance is highlighted by a center door flanked by sidelights. A gentle landscape with shrubs is visible on either side.
Home in Salem
4.98 out of 5 average rating, 191 reviews

Magical Farm Getaway - a must visit!

StephanieRating, 5 stars3 months ago
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!
Superhost
The outdoor pool is surrounded by a chain-link fence and features a concrete deck. Sun lounges and chairs are positioned nearby, with a colorful beach towel draped over a lounge chair. Lush greenery frames the area, providing a serene setting.
Home in Wilmington
4.87 out of 5 average rating, 171 reviews

Adams Farm-"The Little Farmhouse"

Catherine (Lou)Rating, 5 stars4 months ago
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.
Guest favorite
A Colonial home is positioned on a green lawn, showcasing a charming brick façade and a classic porch. Large trees provide shade, while an American flag is displayed proudly by the door. Nearby, a design studio is visible, highlighting the spacious front yard.
Home in Keene
4.93 out of 5 average rating, 211 reviews

The Brick House on Washington Street

PaulRating, 5 stars1 week ago
Great stay and was exactly what we needed for our entire family for a weekend wedding!
Guest favorite
An aerial view captures a modern home surrounded by lush greenery. A tranquil in-ground pool is set within a landscaped area, complemented by a stone fire pit and a gazebo. The exterior features a variety of trees, enhancing the serene atmosphere.
Home in Dorset
4.96 out of 5 average rating, 23 reviews

Idyllic Dorset Home: Serene Escape w/amazing views

StacyRating, 5 stars3 months ago
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!
Guest favorite
A fenced outdoor pool area is surrounded by lush greenery and tall trees. The pool is heated and saltwater, reflecting the sunlight. Adjacent to the pool, a small shaded structure provides additional space and amenities.
Home in Plainfield
4.89 out of 5 average rating, 139 reviews

Historic Home on 17 acres of land. Go escape!

BrandieRating, 5 stars3 months ago
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!! 🤩
Guest favorite
The exterior of a newly built home features a combination of wood and stone accents, with a sloped roof and multiple windows. Surrounded by trees, it is set back from the gravel drive, showcasing a peaceful wooded environment.
Home in Wardsboro
5 out of 5 average rating, 8 reviews

Wander In | Close to Mount Snow & Stratton

KatherineRating, 5 stars3 months ago
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.
Guest favorite
A historic farmhouse with a two-story white exterior is surrounded by lush green grass and trees. A large wrap-around porch features rocking chairs, and a side deck has a dining area with umbrellas. The inviting facade is complemented by bright blue skies.
Home in Granville
4.94 out of 5 average rating, 105 reviews

Historic 1850’s Renovated Farmhouse w/ Pool!

KimberlyRating, 5 stars2 weeks ago
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

Guest favorite
A cozy sitting area is furnished with a plaid-patterned sofa and two leather armchairs. A wooden coffee table sits on a vibrant area rug, and soft lighting is provided by lamps on either side. Natural light filters through the sheer curtains.
Home in Dorset
4.93 out of 5 average rating, 29 reviews

Charming Vermont Retreat

JanetRating, 5 stars7 months ago
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.
Top guest favorite
The exterior of a two-story house is shown, featuring a dark grey facade and multiple large windows that provide natural light. A wooden deck with steps leads to the front door, flanked by snowy terrain and bare trees, creating a calm winter atmosphere.
Home in Winhall
4.96 out of 5 average rating, 24 reviews

Mountain House between Stratton, Bromley, Magic

ChristopherRating, 5 stars3 months ago
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.
Guest favorite
A modern living space is featured, showcasing a mid-century dining table with four black chairs. A plush gray sofa complements the wooden ceiling, illuminated by a circular pendant light. Two framed artworks hang above the sofa, adding a touch of color to the inviting room.
Home in Jamaica
4.92 out of 5 average rating, 99 reviews

The Post Haus: one-of-a-kind modern VT experience

ChadRating, 5 stars1 month ago
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.
Superhost
A spacious living area features a sleek black leather sofa facing a modern television mounted above a brick fireplace. High ceilings are adorned with wooden beams and large windows allow natural light to fill the space, providing a warm and inviting atmosphere.
Home in Winhall
4.71 out of 5 average rating, 17 reviews

Stratton Shuttle, Hot tub, Sauna, 2 Suites 5 STARS

JavierRating, 5 stars2 months ago
Fantastic stay at Christopher’s place. Great communication, hastle free booking experience.
Guest favorite
A bright living area features a large window offering views of lush greenery and distant mountains. Comfortable sofas are arranged around a wooden coffee table, accompanied by a floor lamp and a decorative plant, creating a welcoming space for relaxation.
Home in Winhall
4.92 out of 5 average rating, 26 reviews

Multi-Level Ski Retreat at Stratton Mountain

LiliaRating, 5 stars4 months ago
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!
Guest favorite
A newly constructed wooden home is depicted, surrounded by a snowy landscape. The structure features a blend of modern and rustic architectural elements, including a large porch and multiple windows that reflect the light of a cloudy sky. Natural stone forms a path leading to the entrance.
Home in Winhall
5 out of 5 average rating, 10 reviews

New 6-BR Luxury Home 6 Min from Stratton w/hot tub

VanessaRating, 5 stars1 month ago
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!
Guest favorite
A modern glass house is situated on a gently sloping hill, surrounded by towering trees. The structure features large windows that reflect the natural surroundings, allowing light to enhance the space. Soft grass covers the hillside, leading to the home's entrance.
Home in Guilford
4.92 out of 5 average rating, 49 reviews

Vermont Mirror House

GeorgeRating, 5 stars1 week ago
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.
Guest favorite
A spacious green house with multiple gables sits against a cloudy sky. The inviting entrance features a central door framed by windows and flanked by shrubs. A garage door is visible on the left, adding to the home's functionality and charm.
Home in Winhall
4.93 out of 5 average rating, 14 reviews

Ski Lodge Hideaway: 5 minutes to Stratton Mountain

JackieRating, 5 stars3 months ago
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

Top guest favorite
A charming home is nestled among trees on a peaceful lakefront. A large deck with a red umbrella overlooks the water, while a private dock extends into the lake. Various outdoor activities and relaxation areas are visible, enhancing the serene setting.
Home in Argyle
5 out of 5 average rating, 18 reviews

Lakefront gem

RebeccaRating, 5 stars1 month ago
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!
Superhost
A cozy living area features a comfortable sofa and two armchairs arranged around a circular wooden coffee table. Large floor-to-ceiling windows allow natural light to illuminate the space, providing views of the lush greenery outside. Exposed wooden beams enhance the room's character.
Home in Sunderland
4.71 out of 5 average rating, 31 reviews

Modern, Serene Farmhouse Retreat

JerricaRating, 5 stars3 months ago
This place was exactly what we needed to escape and unwind. So relaxing, cozy and comfortable.
Top guest favorite
The exterior of the home is set amidst wooded surroundings, featuring a dark exterior with a vibrant pink front door. A gravel driveway leads to the entrance, surrounded by autumn foliage. The metal roof complements the natural scenery, enhancing the home's country charm.
Home in Jamaica
5 out of 5 average rating, 40 reviews

2-Bedroom Home, 7 Minutes From Stratton Mountain

PaulinaRating, 5 stars3 months ago
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.
Top guest favorite
The exterior of a charming converted carriage house is showcased, featuring a mix of wood and siding. Lush greenery surrounds the structure, with colorful flower pots placed along the pathway leading to the entrance. A gravel driveway and mature trees add to the serene atmosphere.
Home in Dorset
4.99 out of 5 average rating, 67 reviews

Home in the Heart of Dorset Village

BrentRating, 5 stars2 weeks ago
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.
Guest favorite
The kitchen features modern Samsung appliances, including a stainless steel refrigerator and a gas stove. A spacious island with bar stools invites social interaction, while reclaimed floating shelves display elegant dishware. Natural light enters through the nearby door, enhancing the warm ambiance.
Home in Stratton
4.96 out of 5 average rating, 26 reviews

Antique Charm 8 Mins to Stratton 12 to Mt Snow

JennRating, 5 stars3 months ago
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.
Top guest favorite
Home in Winhall
4.98 out of 5 average rating, 64 reviews

Stratton 35 acres w/Hot Tub, VIP parking pass

GenRating, 5 stars3 months ago
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
Top guest favorite
The exterior of the cottage is partially obscured by tall, colorful wildflowers swaying in the breeze. Sunlight illuminates the scene, highlighting the serene setting surrounded by greenery and trees, with a clear blue sky in the background.
Home in East Dover
5 out of 5 average rating, 50 reviews

Magical Retreat Cottage - Waterfalls Everywhere

DavidRating, 5 stars1 day ago
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.
Guest favorite
A comfortable living area features a sectional sofa adorned with soft pillows and a wooden coffee table. Natural light floods in through a large window, highlighting the wooden wall paneling. A decorative rug rests under the table, adding warmth to the space.
Home in Dorset
4.92 out of 5 average rating, 50 reviews

Mountain View Getaway

OliviaRating, 5 stars2 weeks ago
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

    ﺩ.ﺇ404 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

Destinations to explore

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  2. United States
  3. Vermont
  4. Bennington County
  5. Winhall
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