
Apartment holiday rentals in Winhall
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Top-rated apartment rentals in Winhall
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Popular amenities for Winhall apartment rentals
Weekly apartment rentals

3BR/3BA Hearthstone condo with pool access
Great location in Stratton Village . The condo was perfect and had everything we needed .

Luxury Duplex Condo·Stratton Ski in Ski Out
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😍

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

Your Vermondo awaits: Steps to Lifts & Village.
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!

Downtown Condo - walk to MoCA
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.

Perfect Getaway! Modern & Convenient to Everything
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.

Cute 2BR Stratton Condo halfway up access road
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.

Great Ski In / Ski Out Location!
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

Fully walkable 2BR condo in Ludlow’s village!
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!

Pet Friendly Stratton West
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

Ski Condo 5 Min from Mt Snow
Lovely home, looked just as described, very responsive/ accommodating host. Stunning Mountain View’s whichever direction you drive. Will definitely be coming back here!

Stratton Mountain vacation spot
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.

Newly renovated 2BR on historic Eagle Street.
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!

Mount Snow Close, Great Price, Lots of Room
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.

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

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

Mount Snow Ski Chalet
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.

Cozy Updated 2 Bedroom Corner Condo
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!

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

One Bedroom Suite Near Okemo
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.

Stratton two bedroom condo on a shuttle
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.

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

Lyon Family Lodge - Ski-in/ski-out
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.

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