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28 Rab. I - 30 Rab. I

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16 Jum. I - 18 Jum. I

Compare 288 Vacation Homes in Cheshire with updated reviews, rates, and availability.

"Property was very nice Kirchen could use some additons -starting with a ladle "

SAR 859 total

includes taxes & fees

22 Mar - 23 Mar

"Property was very nice. Quite area. Host was fantastic. "

"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...

SAR 3,758 total

includes taxes & fees

22 Mar - 23 Mar

"The pictures were absolutely spot on! The space was incredibly quiet and cozy, with a warm and inviting atmosphere—even in zero-degree weather. The hot tub was fantastic, and the heated bathroom floors were a luxurious touch. The WiFi worked flawlessly throughout the property. The chef’s kitchen was spacious and well-equipped, making it perfect for cooking. Plus, the rental is conveniently close to town, and the breathtaking mountain views made the stay even more special. Highly recommend!"

"My friends and I stayed at this adorable and HUGE home in this lovely condo complex to spend the weekend at Ski Butternut which was only like 10 minutes away. The host even left us 2 bottles of wine! It had FIVE bathrooms which is unheard of, like anywhere, and the beds were the fancy adjustable kinds. TVs and cable in every bedroom. The fireplace was so luxurious. When the living room TV was giving us some connection issues I think it was a total of like 7 minutes to contact the host/co-host...

"Tom’s cottage was the perfect place for us to stay to enjoy the new year in quiet Lenox. It was centrally located which made exploring town easy and convenient. The check in and out process was super simple and Tom made himself easily accessible throughout the stay. "

"Highly recommend this charming, historic place. Well appointed. Has everything you need for your stay. Cozy…yet plenty of space for everyone. Looks like it was just renovated. Took my daughter and two granddaughters for a ski weekend. Wouldn’t hesitate to come back here. "

"Lovely ski weekend! Best memory: hot tubbing at sunset after skiing with snow falling all around! "

"The location was great and just a short walk to downtown. We thought the pictures on the site were a bit misleading. The house looked a little more open than it actually was, especially in the kitchen. The outside fire pit area was a little run down. A chair was broken and the string lights were down on the ground, water filled and no outlet to plug into. Plenty of bed space for everyone to sleep and beds were comfortable. Plenty of extra sheets and towels and the kitchen was well equipped. We...

SAR 1,818 total

includes taxes & fees

2 Apr - 3 Apr

"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"

SAR 1,234 total

includes taxes & fees

24 Mar - 25 Mar

"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "

"Fantastic home! Clean, well stocked and very comfortable. We had a great time and will be back. The owner was kind, considerate and appreciative of our stay. Thanks again! "

"We had an awesome stay at Nate’s place! The stone architecture and wood oven fireplace gave a truly unique experience, and the house was very spacious. The fully equipped kitchen made for anxenjoyable cooking experience. Nate was also flexible and responsive. Definitely recommend this for your weekend getaway home!"

"The property is great for a group of people lots of bedrooms. Lots of sitting rooms. The kitchen is great for a culinary event - we had a private chef one night. The upstairs den was very cozy-It was a cold weekend with lots of snow- we didn’t want to leave the house !And close to Lenox -and Miraval spaWe would definitely come back next year. "

"Very clean place. Decorated like your grandmother's house. Homey. And you get to use the garage--a big help on a snowy weekend. If you want convenience and cleanliness, this is a great spot. If you want quiet--skip. It's right on Rt. 7 and you have lots of traffic moving by at high speeds. But to their credit, there are many sound machines to drown it out. "

"We had a great weekend stay here with our dog. He loved the backyard and felt right at home. Everything was clean and great location."

"The house was nicer than we expected we had a wonderful time and will recommend to friends."

4 bedrooms, desk, iron/ironing board, WiFi

"Great spot for a ski weekend at Berkshire East. "

"Our group of 8 were happy in this comfy home. The kitchen was well appointed with everything we needed. The bedding, towels and toiletries provided were very much appreciated. The cozy living room with the pellet stove has a beautiful view for morning coffee. "

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Other property types in Cheshire

"We planned to stay at this property in order to ski at Jiminy peak, and it was perfect, not a long drive at all. The barn stays very warm with the individual heaters as well as the wood stove in the middle of the main room. The kitchen was equipped with everything you need, they even had coffee and sugar! .. Communication with the hosts was seamless. We lost power due to a winter storm, the entire area did, and that wood stove worked its magic. The property owners made sure we were alright...