Vacation rentals with outdoor seating in Winhall

Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.

Had a lovely holiday week in Nancy’s home! We felt right at home. The home was cozy and beautifully sun lit in the mornings ! Nancy had decorated before leaving and it was adorable and sweet. The yard was amazing for my 2 large dogs - they ran around and found toys to play with. The area was walkable with sidewalks that were mostly cleared after the snow. Hilly for sure ! Good workout hehe Super close to MassMoCA and the center of North Adams. Walked a few times with the dogs. There’s a dog run near by as well. A short drive from Bennington, Pittsfield and a handful of ski resorts. We had a great stay. Friendly neighbors, communicative host and lovely surroundings :) would love to be back!

Cute Vermont farmhouse that had everything that you needed. We enjoyed Cooking inn and hanging out in the living with the fireplace. The hot tub was so much fun after a cold day on the mountains. There is a cute little coffee shop and super market only 10 minutes away.

My partner and I (and our pups) loved our stay at Mian and Anthony’s home! The home was in a perfect location for what we needed, clean and comfortable, and overall great vibe. ✨ Hosts were super friendly and helpful. We would definitely stay again next time we’re in town!

My family of four loved Christine’s place! She is so thoughtful, leaving yummy snacks plus necessities as well. She’s a great baker and provided us with some yummy treats! The beds were super comfy and cozy, bathrooms were clean and well-equipped and we loved being both close to downtown but also could go hiking out the back door. We feel so grateful to have had such a lovely and relaxing place to stay. Thank you, Christine! ❤️

⭐️⭐️⭐️⭐️⭐️ Amazing Stay with Wonderful Hosts! Our stay at Matt and Diane’s place was absolutely fantastic! From the very beginning, they were incredibly kind, welcoming, and helpful, ensuring we had everything we needed for a smooth and enjoyable visit. Their communication was excellent before, during, and even after our stay, making us feel truly taken care of. The property itself was exactly as advertised—spotlessly clean, well-equipped, and stocked with all the amenities we could ask for. It was the perfect place to relax and feel at home. Their attention to detail and hospitality made all the difference. I would highly recommend this property to anyone looking for a comfortable and stress-free stay. Thank you, Matt and Diane, for being such amazing hosts—we can’t wait to come back!

Dangerously cozy. Quiet at night, but not so secluded that it felt eerie. The cottage itself is stocked with every miscellaneous item you might forget—toothbrushes, soap, cooking spray, local maps, scissors, etc., and was clearly well-cared for and, beyond that, loved. We indulged in a game of Scrabble on a board from 1976: this isn’t any sort of apartment set. People have clearly lived here. Dave was accommodating and understanding when I made my first booking on AirBnb with him, requesting more information about my trip and myself without making me feel like I was under investigation. House is just perfect. Highly recommend booking with Dave.

Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩

This rental was perfect for our family’s overnight ski trip to Okemo. We have two teenaged sons who shared a bedroom. The kitchen had everything we needed to cook breakfast and (most importantly) to meet the AM caffeine needs. The rental was approximately 10 minutes away from Okemo, which was the best part for us. Already planning next February’s ski trip!

Always a great stay at Happy Hour! Our favorite spot.

If you have trouble with steep, narrow stairs please heed the warnings on the listing! We were fine. The heating design was a little challenging at first: the main living room and kitchen were fine (each have a heat pump), but on the cold day we arrived it was hard to get heat into the bedroom and extra back room (no wall units—maybe a portable space heater or two would be a good addition?). We finally turned the heat up, used fans and blankets, and got some warmer days which helped make the entire apartment more comfortable. The extra back room was handy (and a welcome surprise!) for my morning yoga and meditation, and the weather was warm enough on our last full day to sit out on the roof deck. Quiet, easy to get to downtown places, great parking, good local recommendations. Would have been nice to know in advance that the coffee maker was a keureg, but that’s a quibble. Thanks!

I really annoyed my stay at Jaki’s apartment. It was a great location for multiple days of skiing at several resorts, all within an hour’s drive.

Jim was able to accommodate my partner and me at very late notice which was very appreciated. The spot was exactly what we needed and Jim was quick to communicate and get us all set up. The space was clean and private and set up with everything we needed.

Thanks for the host making this place like home. Furnitures are well organized. My partner and I love the sofa in the living room. There is a big sofa and single arm chair sofa. It’s good for staying with partner to kiss cuddle and more. We love the well organized kitchen. Very well-equipped. They even have some stock of food, coffee and tea bags just in case if you are hungry in mid night. We came here for skiing trip. It’s just 15 min to Mt Snow, 1.5h to Okemo. Stratton is also around this area. Great location for mountain staycation.

This property is definitely within the top five Airbnb’s that I’ve ever stayed at! The apartment is absolutely beautiful with no detail missed. The kitchen was impeccable with light snacks provided and coffee/creamer, which is a huge plus for me. The bathroom was spotless with beautiful, plush towels and a lovely washer and dryer set. The living room was very comfortable with a reclining couch. The bed was very comfortable with plush linens. I can’t wait to stay again when I’m working in town.

I had a wonderful stay at Kim’s cozy and charming place in Bennington. Everything was perfect, and I had no issues at all. After long days of skiing, I especially enjoyed relaxing by the fire pit on two evenings—it was a great way to unwind. The location is excellent, close to stores, restaurants, and downtown, making everything easily accessible. I skied at both Stratton and Mt. Snow, and getting to both mountains was a breeze. Overall, I had a fantastic stay and would highly recommend Kim’s place to anyone. Thank you, Kim!

Clean, great location, easy check in/out, and friendly host - would definitely stay again.

Loved Kristin’s place, the best part was that it was right on the mountain. Perfect for a family of 4, will definitely comeback. Beds were comfortable and the living room was very cozy. Loved the mural. Thank you Kristin!

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.

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.

beautiful condo, well maitained and bathrooms new and remodeled. Great location to the ski lifts. He woks great, walls are solid because we couldn't hear the neighbors and all units were full this weekend. Nice fireplace and wifi worked great for the kids and all big flat screen tv's were excellent. Easy kitchen to cook in for the whole family. Best condo we've stayed at in Mt. Snow. Owners answered all our questions and recommendations

We had a great stay at Rafael & Janice’s listing! They were super accommodating with flexible check in and check out, were proactive in checking in during our stay, provided great local recommendations, and were overall super responsive and kind. The condo is lovely, with beautiful furnishings and great attention to detail. We absolutely loved the fireplace; it made for a cozy retreat after a day of skiing. Great views of Mt. Snow from the condo! It is also a prime location with shuttle access to Mt Snow and a short drive to Stratton. We could not recommend this condo enough, and look forward to staying here again soon!

Christine's condo was a perfect fit for my family's trip to Mt. Snow. Comfortable and cozy with ski in/out access. My parents loved having access to the clubhouse to soak in the hot tub.

Great place to stay conveniently located by the mountain base! We enjoyed walking into the village after skiing. Very clean and cozy and had everything we needed and more. Dana was very responsive! Hope to come again next year!!