Condo vacation rentals in Winhall

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Popular amenities for Winhall condo rentals

Weekly condo rentals

Guest favorite
The exterior of the Hearthstone Lodge is showcased, featuring a blend of natural stone and wood materials. Four prominent staircases lead to the entrance, framed by large, wooden arches and wide balcony overhangs. Surrounding greenery adds a touch of nature to the entrance.
Condo in Stratton Mountain
4.88 out of 5 average rating, 8 reviews

3BR/3BA Hearthstone condo with pool access

Jennifer CatherineRating, 5 stars3 months ago
Great location in Stratton Village . The condo was perfect and had everything we needed .
Guest favorite
Condo in Stratton
5 out of 5 average rating, 7 reviews

Luxury Duplex Condo·Stratton Ski in Ski Out

VeronicaRating, 5 stars7 months ago
This was a great place to stay! Super convenient and right in Stratton Mountain village. The hosts were very friendly and responsive. It was easy to communicate. They had every detail covered including shampoo, conditioner and even tissues. We highly recommend this place and would stay here again! Thank you😍
Guest favorite
The image captures a serene lake scene with swimmers enjoying the water near a rocky shore. A sailboat glides peacefully across the sparkling surface, surrounded by lush green hills under a partly cloudy sky.
Condo in Dover
4.95 out of 5 average rating, 60 reviews

Condo w/ great amenities 4-seasons! Ski in Ski out

WifeCherylannRating, 5 stars1 month ago
Excellent location and central to all things fun in southern Vermont. Loved the sports center amenities. Very peaceful considering it was end of mud season and not busy at all. We used the pool, workout facilities and locker room. Even had a fireplace we could use ! Christine was incredibly responsive and welcoming. Would recommend to others and would stay again if in the area.
Top guest favorite
A spacious sitting area features large windows that allow for ample natural light and views of the outdoor space. Cozy blue armchairs surround a distinctive wooden coffee table, creating an inviting atmosphere for relaxation and conversation.
Condo in Stratton
5 out of 5 average rating, 44 reviews

Your Vermondo awaits: Steps to Lifts & Village.

ErinRating, 5 stars2 months ago
We really enjoyed our stay here with our 3 kids! The second bedroom was perfect with the trundle and the bunk beds. The condo was well maintained and exactly as described. The heated pool and hot tubs were great after a day on the slopes. We enjoyed the close walk to the lifts at Stratton as well as the walk to the village. Would highly recommend!
Guest favorite
The fully equipped eat-in kitchen features light-colored cabinetry and a wooden countertop, with a small dining table set for two. White shutters frame the windows, allowing natural light to create a bright atmosphere. A wall art piece with the phrase 'be happy' adds a touch of positivity.
Condo in North Adams
4.89 out of 5 average rating, 28 reviews

Downtown Condo - walk to MoCA

RuthRating, 5 stars2 weeks ago
My husband and I loved our stay at Jo Anne’s place, it was quite,clean private, easy access to parking and very affordable . Stocked with the necessities.
Guest favorite
Colorful sailboats are seen gliding over a calm lake, surrounded by dense green hills. The vibrant sails in shades of blue, yellow, and orange create a striking contrast against the tranquil water, reflecting the natural beauty of the surroundings.
Condo in Ludlow
4.96 out of 5 average rating, 23 reviews

Perfect Getaway! Modern & Convenient to Everything

RohithuRating, 5 stars2 weeks ago
Great Place to stay. It’s small yet enough for two people which is what we wanted. It is very clean and had all basic cooking stuff. It is a cute little place to spend a weekend in a serene location. We had a peaceful stay. Jim patiently responded to all our questions before checking-in. We would love to stay here again and would definitely recommend friends.
Guest favorite
A combined living and dining area features a plaid sofa and an armchair, accompanied by a recliner. A wooden coffee table sits centrally, and a large sliding glass door invites natural light while providing access to a small outdoor area.
Condo in Winhall
4.81 out of 5 average rating, 77 reviews

Cute 2BR Stratton Condo halfway up access road

LisaRating, 5 stars4 months ago
Can’t beat the location to Stratton mountain. Even with 10 inches of snow, only took us less than 10 mins. Place is clean, beds are super comfortable and the place has lots of extras, blankets, pillows, throw blankets and the heat worked great in all rooms. Nice and warm and cozy with it being in low 20 degree temperatures. Definitely plan on staying again for our next ski trip.
Top guest favorite
The spacious great room features a stone fireplace, providing a focal point for relaxation. Comfortable seating is arranged invitingly, with a wooden coffee table at the center. Large windows are adorned with light-filtering curtains, allowing soft natural light to enter, while a dining area is visible in the background.
Condo in Stratton
5 out of 5 average rating, 21 reviews

Great Ski In / Ski Out Location!

KentRating, 5 stars2 months ago
The ability to walk a very short distance to the Tamarack Chair, thereby avoiding the crowds at the main lodge area, was really wonderful. And if one wants to go to the village to shop, have dinner, drinks, the village was an easy 5 minute walk. Absolutely loved the location.

Pet-friendly condo rentals

Guest favorite
A cast iron gas fireplace is centered on a stone hearth, providing warmth. A wooden ladder holds colorful blankets, while a woven basket filled with magazines is placed nearby. Light filters in through a window with horizontal blinds, enhancing the cozy ambiance.
Condo in Ludlow
4.89 out of 5 average rating, 38 reviews

Fully walkable 2BR condo in Ludlow’s village!

StephaneRating, 5 stars6 months ago
We had the pleasure of staying at Ryan’s place on Tapper Street in Ludlow, from August 31 to November 30, and it was absolutely fantastic! The house was the perfect relaxing retreat. The living room was super comfortable—ideal for cozy nights watching TV. Our kids especially loved the bunk beds, which were a big hit! The house was well-equipped with all the amenities needed for a long stay, making it feel like a home away from home. Ryan was a wonderful host, always responsive and helpful. His recommendation to try DJ’s Restaurant was spot on—the Cajun blackened salmon was incredible! We can’t recommend this place enough and would love to stay again in the future. Thanks, Ryan, for a wonderful stay!
Superhost
A cozy living area features a large blue sectional sofa, equipped with a coffee table at its center. A mounted television is visible on the wall, alongside natural light from a nearby window. Decorative elements include a floor lamp and a small side table.
Condo in Winhall
5 out of 5 average rating, 3 reviews

Pet Friendly Stratton West

DoojinRating, 5 stars3 months ago
Little smaller than what the photo showed. Overall exactly as stated in the description. Location is great and the host is extremely responsive and friendly. One of the better hosts in my experience
Guest favorite
A cozy living room showcases two plush couches and a small wooden coffee table. A gas stove is nestled in a brick corner, while sliding doors offer views of the outdoors. Colorful lights frame the window, adding a touch of charm to the space.
Condo in Dover
4.9 out of 5 average rating, 52 reviews

Ski Condo 5 Min from Mt Snow

JadeRating, 5 stars3 weeks ago
Lovely home, looked just as described, very responsive/ accommodating host. Stunning Mountain View’s whichever direction you drive. Will definitely be coming back here!
Guest favorite
A two-story condo is shown with a snow-covered roof and a well-maintained exterior. A vehicle is parked in front, and snow blankets the surrounding area. The backdrop features a snow-covered mountain, displaying ski trails that contour the slopes.
Condo in Stratton
4.9 out of 5 average rating, 69 reviews

Stratton Mountain vacation spot

CandaceRating, 5 stars2 months ago
We had a great stay at this cozy condo, perfectly located on a shuttle route to Stratton Mountain. The convenience of being just minutes from the slopes made our ski trip stress-free.
Guest favorite
Condo in North Adams
4.96 out of 5 average rating, 74 reviews

Newly renovated 2BR on historic Eagle Street.

CaryRating, 5 stars1 week ago
Katie's place was great--very stylish, conveniently located, and well maintained/cleaned. Loved the renovation of the older building to create a contemporary space while incorporating some of the historic beams and brick work into the design. The living area and kitchen were spacious, comfortable, and well-appointed. The beds were very comfortable. It was great to have a dedicated parking space. The street is busy and well lit, so we were happy to have ear plugs and eye shades when trying to sleep. The location is convenient to MassMOCA and some great restaurants. All in all, a fantastic stay!
Guest favorite
The chalet duplex features a two-toned exterior with a dark wooden upper level and a white lower level. A spacious outdoor deck is visible, complemented by greenery and well-maintained shrubs, creating a serene setting within a natural landscape.
Condo in Dover
4.85 out of 5 average rating, 169 reviews

Mount Snow Close, Great Price, Lots of Room

PeteRating, 5 stars2 months ago
Very close to Mount Snow. Walking distance to market, coffee house and Dover Bar and Grill. A dog friendly rental with everything you need for a ski trip.
Guest favorite
The exterior of a multi-story grey building is shown, featuring a sloped roof and several square windows. A ramp leads to the main entrance, which is adorned with light fixtures and framed by greenery, including bushes and grass.
Condo in Londonderry
4.95 out of 5 average rating, 61 reviews

Magical Ski-In/Ski-Out Condo at Magic w/ game room

RobbyRating, 5 stars5 days ago
This kind of space is why AirBNB was invented; it was clearly a space where the owners also spend time, and it felt like staying at a friend’s clean, cozy home. Too many AirBNBs are basically fake hotels run by people trying to earn money with spaces they’ve never lived in, and this was a breath of fresh Vermont air! I can’t say enough nice things about this space or the hosts!
Top guest favorite
A serene sleeping area features a spacious bed with plush bedding, complemented by side tables on either side. A warm lamp casts a gentle glow, illuminating an artistic wall hanging that adds character to the room. Soft textures enhance the inviting ambiance.
Condo in Ludlow
4.95 out of 5 average rating, 21 reviews

The Otto: A Warm and Cozy Ski In + Ski Out Lodge

KatrinaRating, 5 stars2 months ago
Very responsive and friendly hosts. The living room fireplace setup was perfect for the cold weather & the entire place was exactly as promised and in an ideal location. Walk right over to the slopes and ride down to the lift. Great experience! Would certainly book again!

Condo rentals with a pool

Guest favorite
A snowy landscape showcases the mountain in the background with ski trails visible. The foreground features a winter scene with snow-covered ground and trees. A building is partially visible on the left, adding to the serene atmosphere.
Condo in Dover
4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

BarryRating, 5 stars3 months ago
Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.
Superhost
An indoor pool area is featured, surrounded by large windows offering views of the outdoors. Lounge chairs are arranged neatly along the poolside, and the clear water reflects the overhead lighting, creating a calming environment.
Condo in Dover
5 out of 5 average rating, 11 reviews

Cozy Updated 2 Bedroom Corner Condo

NicoleRating, 5 stars28 months ago
Greg has to be the most responsive, accommodating host I've ever had the pleasure of renting from. He gave me clear instructions, responded the minute I sent a question, and was very generous regarding check in and check out. What a great guy! The condo itself is in a great location. We didn't use the Moover but the stop is right outside the building's door. Like many ski condos it's basic but cozy. The neighbors were really audible in the bedroom, but we may have just had a weekend with some loud people next door! The best part (besides how great Greg was) is the view. It's so lovely to look out over the ski mountain. Overall a great value and a wonderful host. Thanks, Greg!
Guest favorite
An indoor pool area is showcased, featuring a rounded pool with clear blue water. Large windows provide natural light and views of the snowy landscape outside. Seating areas are visible along the sides, contributing to a spacious ambiance.
Condo in Dover
5 out of 5 average rating, 17 reviews

'Bear Paw Lodge' w/Hot Tub* at BASE of Mt Snow

JoelRating, 5 stars2 months ago
My family of four had plenty of space for a relaxing weekend. Weather did not permit skiing but Mt Snow was right next door and Okemo ~60 mins away. Nice amenities in a great location.
Guest favorite
An indoor pool area is highlighted by a spacious swimming pool. Natural light enters through large windows, offering views of the outdoor patio. Seating areas with chairs are arranged along the walls, complemented by warm-toned curtains.
Condo in Ludlow
4.93 out of 5 average rating, 110 reviews

One Bedroom Suite Near Okemo

ChristopherRating, 5 stars2 months ago
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.
Guest favorite
A welcoming entrance to Crown Point is depicted, featuring a large sign with bold lettering. The sign is framed by a wooden structure and surrounded by vibrant flowers in various colors, adding a touch of natural beauty to the landscape.
Condo in Stratton
4.93 out of 5 average rating, 15 reviews

Stratton two bedroom condo on a shuttle

DrewRating, 5 stars3 months ago
Megan’s place was great for a weekend of skiing at Stratton. Right on a shuttle route that picks you up at the front door and is very reliable. Clean and comfortable. Megan was extremely helpful and responsive throughout the whole process from booking to check in and check out.
Superhost
A cozy living area features a mix of orange and brown sofas, complemented by a wooden coffee table. A stone fireplace is positioned beneath a wooden panel wall, with a television mounted nearby. Large windows illuminate the space, offering views of the snowy outdoors.
Condo in Dover
4.89 out of 5 average rating, 9 reviews

Pool & hot tub! Hiking, nature and mountain views!

ToniRating, 5 stars3 months ago
We loved the proximity to Mount snow, and the layout of the place was cozy and comfortable. We loved the newly renovated kitchen and all kitchen supplies were new. We didn’t get to use the amenities but we loved the sauna and hot tub offerings!
Guest favorite
A cozy living area is highlighted by a stone fireplace, topped with a wooden mantle. A large television is mounted on one wall, while plush seating surrounds a wooden coffee table. Stacked firewood is neatly arranged beside the fireplace, adding to the warm ambiance.
Condo in Dover
5 out of 5 average rating, 23 reviews

Lyon Family Lodge - Ski-in/ski-out

BethRating, 5 stars5 months ago
Great location, ski on ski off and very nice community not far from restaurants. Jared was very responsive and flexible with check in time. Overall a great condo on the mountain and would stay here again.
Guest favorite
The exterior of the building is framed by flowering plants and greenery, creating a welcoming entrance. A wooden pathway leads to the front door, flanked by manicured landscaping and decorative rocks. Large windows illuminate the interior, allowing for natural light.
Condo in Dover
4.96 out of 5 average rating, 24 reviews

Mt. Snow Condo with Pool-Hot Tubs-Sauna MTN Views

Axuan VrolijkRating, 5 stars2 months ago
Had a lovely stay at Leah’s condo. Very comfy and cozy and super close to Mt Snow!

Quick stats about condo rentals in Winhall

  • Total rentals

    30 properties

  • Nightly prices starting at

    R1,613 ZAR before taxes and fees

  • Total number of reviews

    580 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    10 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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