Condo vacation rentals in Berkshire County

Our family loved the stay ! Place was beautiful, clean and with lots of activities for the kids. Highly recommend and definitely coming back soon.

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.

Jiminy Peak is a great family mountain. Christina's place is perfectly located to do everything right out your back door. Christina was an excellent host. Thank you.

This is our second time staying and we loved it even more the second time. Christina was lovely to book with and the unit we were put in had recently been renovated so it was in great shape. You really can't beat this place for a winter family vacation. The space was clean and well appointed. I'm very finicky when it comes to hotel cleanliness, there were a few notes I'd give on the space but overall I was very happy with the space and our overall stay. The staff at Wyndham were very helpful and friendly. We will definitely return again!

Our second year staying here and making wonderful family memories. The condo was clean and cozy. Gorgeous view of the mountain and easy ski in/ski out. Everything you need is stocked and ready. We look forward to rebooking for next year.

The condo was a great location, walkable to stores, gym, shops, even that Mass Moca place everyone obsessively talks about. I stayed for 8 weeks on a work contract and Joanne the host was lovely enough to help me with parking. You can limited meter park (day/night are both limited) or you can buy a parking pass for the lot just a quick minute walk away. No issues! The condo was clean, stocked, and comfortable. As for the noise comments in prior posts, I personally don’t mind city noises. I adapted quick. But to each their own. I would gladly stay again!!!! Loved it.

Had a great stay at Jo-Anne’s for a wedding as MASS MoCA. Space was clean and cozy. Bed and pillows were comfy. Very walkable to places around town. The cars driving by were a little loud for a light sleeper, but with some earplugs it was fine. Jo-Anne was very helpful and responsive.

Very nice spot for one person or a couple. Convenient access to JP base area and amenities. Neat and tidy space, nicely appointed. Great communication from owner.

Great stay! Listing as described. My family really enjoyed our stay.

This is our second time staying and we loved it even more the second time. Christina was lovely to book with and the unit we were put in had recently been renovated so it was in great shape. You really can't beat this place for a winter family vacation. The space was clean and well appointed. I'm very finicky when it comes to hotel cleanliness, there were a few notes I'd give on the space but overall I was very happy with the space and our overall stay. The staff at Wyndham were very helpful and friendly. We will definitely return again!

Our second year staying here and making wonderful family memories. The condo was clean and cozy. Gorgeous view of the mountain and easy ski in/ski out. Everything you need is stocked and ready. We look forward to rebooking for next year.

Our family loved the stay ! Place was beautiful, clean and with lots of activities for the kids. Highly recommend and definitely coming back soon.

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.

Jiminy Peak is a great family mountain. Christina's place is perfectly located to do everything right out your back door. Christina was an excellent host. Thank you.

Great stay! Listing as described. My family really enjoyed our stay.

This is our second time staying and we loved it even more the second time. Christina was lovely to book with and the unit we were put in had recently been renovated so it was in great shape. You really can't beat this place for a winter family vacation. The space was clean and well appointed. I'm very finicky when it comes to hotel cleanliness, there were a few notes I'd give on the space but overall I was very happy with the space and our overall stay. The staff at Wyndham were very helpful and friendly. We will definitely return again!

Our second year staying here and making wonderful family memories. The condo was clean and cozy. Gorgeous view of the mountain and easy ski in/ski out. Everything you need is stocked and ready. We look forward to rebooking for next year.

The condo was a great location, walkable to stores, gym, shops, even that Mass Moca place everyone obsessively talks about. I stayed for 8 weeks on a work contract and Joanne the host was lovely enough to help me with parking. You can limited meter park (day/night are both limited) or you can buy a parking pass for the lot just a quick minute walk away. No issues! The condo was clean, stocked, and comfortable. As for the noise comments in prior posts, I personally don’t mind city noises. I adapted quick. But to each their own. I would gladly stay again!!!! Loved it.

Had a great stay at Jo-Anne’s for a wedding as MASS MoCA. Space was clean and cozy. Bed and pillows were comfy. Very walkable to places around town. The cars driving by were a little loud for a light sleeper, but with some earplugs it was fine. Jo-Anne was very helpful and responsive.