Apartment holiday rentals in Winhall

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Popular amenities for Winhall apartment rentals

Weekly apartment rentals

Guest favourite
Apartment 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 favourite
Apartment 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 favourite
Apartment 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 favourite
Apartment 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 favourite
Apartment 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 favourite
Apartment 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 favourite
Apartment 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 favourite
Apartment 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 apartment rentals

Guest favourite
Apartment 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
Apartment 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 favourite
Apartment in West 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 favourite
Apartment 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 favourite
Apartment 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 favourite
Apartment 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 favourite
Apartment 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 favourite
Apartment 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!

Apartment rentals with a pool

Guest favourite
Apartment 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
Apartment 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 favourite
Apartment 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 favourite
Apartment in Proctorsville
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 favourite
Apartment 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
Apartment 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 favourite
Apartment 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 favourite
Apartment 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 apartment rentals in Winhall

  • Total rentals

    30 properties

  • Nightly prices starting at

    ₹7,747 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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  3. Vermont
  4. Bennington County
  5. Winhall
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