Condo holiday rentals in The Berkshires

Think this is our third time staying at the condo and again it was great. Love being able to walk across the street to the mountain, renting equipment from Equip Sports is very convenient. In our opinion the condo has everything you need for a family of 4. Can’t wait until next year.

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.

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.

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.

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!!

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.

beautiful bright and modern this house was perfect for our stay. The host was very friendly and helpful. We had an issue with a nightlight and they fixed it right away. Five stars! I would highly recommend

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.

Cozy apartment, walking distance from the water front. Had a great weekend getaway.

This is my second stay at Daniel’s, and it was just as good as the first! I love the location of his place in relation to the mountain. It’s a quick walk up the parking lot to the trails/lifts. Most importantly, my pups feel right at home, and they know his place now! His home is always clean and the linens/towels always smell fresh! I told him I will be coming back multiple times throughout the snow season to go boarding. He is very responsive and helpful and would go out of his way if need be! Overall, 12/10 recommend Daniel’s spot!

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.

We had a great time staying at Kens place! Ken was very responsive and accommodating! Thank you!

A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.

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!

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.

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.

We booked the place last minute and Tony was very nice to accommodate us. The are really responsive and had a lot of great recommendations. The place was very warm and homey. We enjoyed the stay very much!