Apartment holiday rentals in Winhall

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Popular amenities for Winhall apartment rentals

Weekly apartment rentals

Top guest favourite
Apartment in Ludlow
5 out of 5 average rating, 32 reviews

2 BR/2BA Ski In/Ski Out Condo on Okemo- Sleeps 6

AmberRating, 5 stars3 months ago
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!
Guest favourite
Apartment in Dover
5 out of 5 average rating, 15 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

AlexanderRating, 5 stars2 months ago
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.
Guest favourite
Apartment in Dover
5 out of 5 average rating, 16 reviews

Seasons Lodge | Trailside Condo w/ Fireplace!

PaulRating, 5 stars3 months ago
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.
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😍
Superhost
Apartment in Stratton
5 out of 5 average rating, 4 reviews

Stratton Slopeside Retreat

Wei-YingRating, 5 stars4 months ago
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! ⛷️
Guest favourite
Apartment in North Adams
4.89 out of 5 average rating, 27 reviews

Downtown Condo - walk to MoCA

ZekeRating, 5 stars1 week ago
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.
Guest favourite
Apartment in Stratton
5 out of 5 average rating, 22 reviews

Walk to Lift - 2 Bedroom Condo - Newly Renovated

ChristianRating, 5 stars2 months ago
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
Guest favourite
Apartment in Proctorsville
4.89 out of 5 average rating, 53 reviews

One Bedroom Suite Near Okemo

EileenRating, 5 stars3 months ago
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

Superhost
Apartment in Ludlow
4.89 out of 5 average rating, 37 reviews

Fully walkable 2BR condo in Ludlow’s village!

MatthewRating, 5 stars13 months ago
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..
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 Dover
4.97 out of 5 average rating, 29 reviews

Mt Snow Condo, 4-min Walk to Sundance Dog Friendly

GaryRating, 5 stars2 months ago
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!
Guest favourite
Apartment in West Dover
4.9 out of 5 average rating, 52 reviews

Ski Condo 5 Min from Mt Snow

JadeRating, 5 stars2 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 stars5 days 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 Londonderry
4.95 out of 5 average rating, 60 reviews

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

CarlRating, 5 stars2 months ago
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!
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 Stratton
4.93 out of 5 average rating, 15 reviews

Stratton two bedroom condo on a shuttle

DrewRating, 5 stars2 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.
Guest favourite
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!
Guest favourite
Apartment in Ludlow
5 out of 5 average rating, 9 reviews

3BR with pool, golf, lake, MTB & hiking trails

SheilaRating, 5 stars3 months ago
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

Destinations to explore

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  3. Vermont
  4. Bennington County
  5. Winhall
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