Condo vacation rentals in The Berkshires

The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.

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.

Cullen was an exceptional host. The space was exactly as described, with plenty of supplies. Communication was stellar. The condo had plenty of extras like clean linens and blankets, there were even additional chargers set up and toiletries if we needed. The beds are comfortable. The bathrooms very clean and updated. Parking right in front. We felt safe and comfortable. This AirBnB is 5 minutes to Windham mountain and minutes from Town. Plenty of places to eat and shop. I highly recommend this Host and property. If we ever go back, we will try to re-book with Cullen.

Great condo at Mt Snow. Very clean and organized. Location is on the mountain. It requires some steep walking for ski in/ski out so keep in mind for younger kids while also carrying their gear. My kids are older so it wasn’t an issue for us but worth mentioning. Eric is the perfect host - always reachable and responsive. Super accommodating when he’s able to be. We got unlucky wind hold weather and he offered to extend our check out if we wanted to ski an extra day to make up for it. Truly awesome. Can’t go wrong.

I highly recommend Suzanne's place for anyone visiting Windham! She was incredibly responsive and helpful throughout the booking process and my stay. As someone who travels constantly for work, my schedule can be quite unpredictable, and Suzanne was unbelievably accommodating and flexible with my changing needs. I truly appreciated her understanding and willingness to work with me. The location is fantastic, right in the heart of Windham, and the view of the ski resort from the back deck was an unexpected bonus! I only wish I could have stayed longer. I'm already looking forward to my next visit, not just for winter skiing, but also to explore the beautiful surroundings throughout the year.

Noah’s unit was absolutely wonderful. I’m not sure if the listing says this but it’s literally in front of a lift! The ski in ski out isnt a short walk. It’s right in front of the doorway. Also I’ve never been so close to a CAT grooming the trails. The unit itself was well stocked, with a great fireplace and spacious three bedrooms. Noah was responsive and very easy to communicate with. And very accommodating esp for a last minute trip! We’d love to return to this place!

It was exactly how described by management and pics. We felt at home and kitchen had everything one needs. Greg the manager was incredibly responsive and professional…. We would go back.

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.

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

Second stay at William’s. Loved it again the second time, great area and super close to Mt Snow resort. Great restaurants and of course the Snow Republic Brewery nearby. Thanks for the great stay!

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.

Could not recommend this place enough! Darla and Matthew are extremely communicative, sent lots of great recommendations, the house is very cozy and well-stocked, the neighborhood is walkable to lots of great shops and food, and the check in and check out process was a breeze! Would definitely stay again. An amazing value for the price.

Hannah was extremely responsive at all times. She even provided us with Oat Milk for our coffee! The water does have a sulphur odor but no worries there is a big water dispensing for drinking if so desire. Place was clean, quiet and perfect for our stay in the Hudson Valley.

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.

Great location for ski trip to Mt Snow; Okemo too. Lots of space and nice touches for skiers: mudroom, washer/dryer, great water pressure. Plenty of good restaurants nearby.

Place was perfect! Right on the mountain for easy access to Magic Mountain. The kids loved the game room! Patrick and Erin were easy to communicate with and very responsive. We can’t wait to come back next year!

Anne is an amazing host and this townhouse is fabulous. Perfect for a mountain stay. Comfortable, spacious, great view of the mountain, clean, modern yet cozy. Very convenient to everything in the area. I cannot say enough about it, but having such a great host was the cherry on top, especially since we were there for an extended period!! You cannot go wrong!

We had a wonderful stay at Jiminy Peak.. hosts were super quick to respond with any questions. Very easy check in and check out. Will definitely be staying again in the future!

Lina was so responsive and helpful. Location could not have been more perfect. Such a lovely find! Thank you, Lina!

Thanks Lauren! We enjoyed your lovely place!

Christine is very easy to work with and very responsive. she answered us back right away before and during our stay. the place is great! very cozy and comfortable. I can't wait to go back to her place next time we're in town!

Our stay at Carl’s listing was more than we could ask. The location is perfect to the mountain and the shops and restaurants in the village. Carl was very helpful for the check in process and was very responsive. The space was very large and clean. We had the best time and I would certainly stay here again in the future!! The amenities at the lodge were amazing and the lodge manager was so incredibly helpful and friendly as well. A happy and fun vacation!!

For our family of three this home fit us perfectly. You CAN certainly have more guests but it truly fit our needs. The set up was VERY spacious and cozy at the same time. The women at the desk are so kind and very good at their jobs. Not only did we feel at home when we arrived to our place, meeting them made us feel even more welcome. The castle was exquisite and an amazing experience in itself. The quaint town of Ludlow is a heart beat away with everything you need. All and all we can't say enough about how satisfied we are with Andy's home, the pricing, the staff and location! Our experience was amazing, memorable and we will be returning for sure next year! We are planning to come with our best friends next year & their kids because of your amazing home & our fantastic experience! 😁 Thank you again for opening your home to our family! The Baers

Everything about this stay was amazing. Victoria is an amazing host, very welcoming and helpful. You can tell she takes pride in her home and community. I look forward to staying with her again in the future.