
Apartment holiday rentals in Winhall
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Top-rated apartment rentals in Winhall
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Weekly apartment rentals

2 BR/2BA Ski In/Ski Out Condo on Okemo- Sleeps 6
This was our second time staying at Lauren's beautiful home, and it certainly won’t be our last! The location is absolutely perfect—right on the mountain, making it incredibly convenient! The condo itself is beautifully appointed and stocked with everything you could possibly need for a comfortable stay. One of our favorite features was the wood-burning fireplace, which added a wonderful touch to our evenings after a long day on the slopes. Lauren is a gracious host, always attentive and ready to help with anything we needed. We recommend her place to all our family and friends and look forward to returning next year for more unforgettable memories! Thank you, Lauren, for another fantastic stay!

Slopes N Seasons | Trailside Condo at Mount Snow
We loved our stay! Everything was immaculate. New. Even ready with some fun board games and a Bluetooth speaker. The location was excellent, and we had a great time! We definitely recommend and would stay again.

Seasons Lodge | Trailside Condo w/ Fireplace!
Perfect place for a family stay at Mount Snow. Convenient ski on/ski off location just as advertised. Clean and comfortable. The sports complex is great spot for after skiing with full fitness center, pool, hot tub and locker rooms. Would definitely rent again.

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😍

Stratton Slopeside Retreat
We were looking for a fun ski weekend with friends and Sierra’s place was perfect. Close to the Tamarack lift, it was great for ski-in/ski-out. The unit was cozy with plenty of room. It had everything we needed and we’re already looking forward to next year! ⛷️

Downtown Condo - walk to MoCA
This was such a special place, staying in a flatiron building off of the ecclectic Eagle Street. It was nice to be within walking distance to a lot of vacation-y places. And it was also within a quick walk to Mass MoCA. Jo-Anne's place is highly recommended. She paid attention to detail during booking & checking-in processes, and helped make me feel comfortable knowing all the info needed for a stress-free stay.

Walk to Lift - 2 Bedroom Condo - Newly Renovated
This place is AWESOME hence why we have come back multiple times and plan to come back again. James is very responsive and his place is perfectly clean and orderly every time we stay. 10/10

One Bedroom Suite Near Okemo
Perfect location when skiing at Okemo. Very close to the general store. The kids loved the pool and the games in the lobby. Staff was very friendly and helpful.
Pet-friendly apartment rentals

Fully walkable 2BR condo in Ludlow’s village!
I had an excellent stay at Ryan’s place. It was exactly as advertised - clean and peaceful. It was honestly a wonderful time. The only slight issue is that it is directly in front of a main road, so you do hear some traffic in the bedroom, but Vermont being as quiet as it is, this is pretty much over by nine or 10 o’clock and I slept well and it really wasn’t a problem. Ryan was a great host and very responsive to any issue I might’ve had. During my month-long stay there was another group who rented the apartment above who were breaking the quiet time rules after 10 PM and partying until 2am. Ryan asked them to leave. To me this is the sign of a truly great host who did something uncomfortable to make my stay a good one. I highly recommend the place..

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

Mt Snow Condo, 4-min Walk to Sundance Dog Friendly
Perfect stay for skiers who want to stay close to the resort! The bedrooms are spacious, the living room is cozy, and the kitchen is perfect for prepping meals. The hosts are incredibly responsive and lovely to chat with - would definitely stay again!

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!

Magical Ski-In/Ski-Out Condo at Magic w/ game room
We had a great time with our family of four! The kitchen was fully stocked and the location was great! Perfect for a family ski getaway. Thanks so much for everything!

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.

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!

3BR with pool, golf, lake, MTB & hiking trails
David and Shannon were great hosts. Place was as pictured and very nice. Would recommend it to anyone.
Quick stats about apartment rentals in Winhall
Total rentals
30 properties
Nightly prices starting at
₹7,719 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
- Jiminy Peak Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- 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
- Mount Sugarloaf State Reservation
- The Shattuck Golf Club
- Lake George Expedition Park
- Dorset Field Club
- Autumn Mountain Winery
- Baker Hill Golf Club
- Pineridge Cross Country Ski Area
- Hildene, The Lincoln Family Home
- Clarksburg State Park
- Ekwanok Country Club