Photo by Ed Gaffny

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

"This beautiful carriage house is ingeniously designed with no wasted space. Surrounded by nature, it is totally private, yet it is two minutes from shops and restaurants. The window seats are sublime and the heated floors offered relief after afternoons spent hiking in the cold. "

AED 837 total

includes taxes & fees

2 Apr - 3 Apr

"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...

AED 3,801 total

includes taxes & fees

4 Apr - 5 Apr

"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. "

"This property was in an incredible location with a nice cozy feel. It was perfect for my family of 6. I highly recommend this place!"

"Was as nice as the pictures. A plus for a very comfortable king sized bed! Right in town for walking to shops and restaurants. Thank you!"

"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. "

"Had a great long weekend getaway in Lanesboro. The property manager was super communicative, which was helpful. Would highly recommend!"

"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...

"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "

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

AED 1,161 total

includes taxes & fees

2 Apr - 3 Apr

"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! "

"Ben and I enjoyed a good long weekend at the correctly described Beautiful Lenox Home. Mary, your host, has thought of everything to help you feel comfortable and very quickly to adjust to your home away from home. It is very well located so that you can easily visit the many places of interest nearby. The rules for checking in and out were clear and simple. We are delighted give this a 5-star rating. David and Ben will return, for sure!"

"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."

"Cozy home with a cabin like feel. Plenty of room and warmth. The 3 bedrooms accommodated our group perfectly! Easy check in instructions"

"This place is immaculate and the host is responsive. We stayed here to ski in Mount snow which is about 25 minutes drive. We arrived later in the evening and the place was warm and cozy. "

AED 1,757 total

includes taxes & fees

8 Apr - 9 Apr

"We had a wonderful time at this property! It was perfect for what we wanted- a place to ourselves in nature with beautiful views. Host was great! Would definitely recommend! "

"Great spot, owners easy to work with. All excellent ! "

"Terrific location, centrally located in the Berkshires, and easy access to Lenox. The stairs were quite steep, which might make it challenging for anyone with mobility challenges. "