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Compare 18 Farmstay in Cheshire with updated reviews, rates, and availability.

Modern Country Farmhouse, Walking Distance to Lake

10.0 out of 10, Exceptional, (5)
"Everything was really nice…well equipped with all you would need"
Modern Country Farmhouse, Walking Distance to Lake

Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!

9.6 out of 10, Exceptional, (14)
"Apartment was clean, bright with comfortable beds. Great location for Berkshires visit, close to Tanglewood and all places fun. Only drawback for us (me and two college friends) was that we brought food for breakfasts and it’s not set up for eating in. No sink in the small kitchen so paper plates and plastic utensils are provided. Small but useful refrigerator. Only a microwave. Small coffee maker but Jodi nicely provided lots of coffee so we weren’t ornery in the morning! Brought in picnic food...
Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!

Charming Farmhouse - quiet, private & peaceful

9.6 out of 10, Exceptional, (62)
"Was a beautiful old farm house, very private location and exactly what we where looking for!"
Charming Farmhouse - quiet, private & peaceful

Country living with hill town views above the clouds!

Country living with hill town views above the clouds!

Large, family-friendly farmhouse located in the beautiful Berkshires

9.8 out of 10, Exceptional, (31)
"The Hart's family have a beautiful home full of wonderful historical artifacts, comfortable furniture, and well stocked kitchen and bathrooms. We loved the wide plank floors, working fireplace, and modern day wifi. Thank you for sharing this wonderful property."
Large, family-friendly farmhouse located in the beautiful Berkshires

Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.

9.0 out of 10, Wonderful, (2)
"A very quaint and well appointed house in a lovely neighborhood."
Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.

Play Area, Crib, 11 Acre Farmhouse

10.0 out of 10, Exceptional, (7)
"The nearly 200-year old Carley Farmhouse nestled amidst the Vermont hills is a real keeper! The natural beauty of the area is stunning, and nature lovers will appreciate the bird chatter, occasional monarch butterfly, starry skies, complete with fireflies in the yard! Gather chairs around the firepit in the yard at night and enjoy it all. Inside, there are several living areas including a small back sunporch that is a quiet retreat both during the day and at night. We didn't end up using the...
Play Area, Crib, 11 Acre Farmhouse

Rural charm a mile from Berkshire East Ski Resort and 29 miles from Mt. Snow.

9.8 out of 10, Exceptional, (10)
"Perfect place for our family for a weekend wedding in the area. Comfortable picturesque and very clean."
Rural charm a mile from Berkshire East Ski Resort and 29 miles from Mt. Snow.

Historic 1817 Berkshire Farmhouse- Close to Everything!

10.0 out of 10, Exceptional, (1)
"A sweet little farm house perfect for a long weekend getaway. We love the lofty primary bed room and excellent mattress, exposed beams and well-supplied and modern kitchen. Great location between Lee and Lenox, made it easy to get all around the Berkshires. All the equipment and appliances m the house were clean and updated. Quiet neighborhood, lovely and large state forest right close by. "
Historic 1817 Berkshire Farmhouse- Close to Everything!

Berkshire Rural Retreat

10.0 out of 10, Exceptional, (19)
"Wonderful spot, quiet and secluded but still close to a ton of stuff! Great kitchen and house, easy for 4 adults and 4 kids. Lots to do outside also. Would recommend and will look to stay again if we’re out in the Berkshires again!"
Berkshire Rural Retreat

NEW RENO - Chalet-style farm loft near Tanglewood

The price is SAR 282
SAR 642 total
includes taxes & fees
22 Jan - 23 Jan
NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Historic Loft w/views of the Berkshires

10.0 out of 10, Exceptional, (3)
"We were attending a weekend class. The bed was very comfortable and the apartment had everything we needed. The owner was very responsive. I would stay here again."
The price is SAR 402
SAR 766 total
includes taxes & fees
16 Jan - 17 Jan
NEW RENO - Historic Loft w/views of the Berkshires

Restored historic farmhouse on 25 private acres

10.0 out of 10, Exceptional, (1)
"Beautiful property, very well maintained and with good access to nearby towns and attractions. We enjoyed the swimming pond and sampled the garden produce. A lovely place to vacation."
Restored historic farmhouse on 25 private acres

Secluded 19th century Farmhouse with mountain views

10.0 out of 10, Exceptional, (1)
"We had a great time on our recent trip to Berkshires. It was due largely in part because of some excellent and charming accomodations at Jeff's family farmhouse. Our large group loved the farmhouse's layout, old world charm and beautiful property."
Secluded 19th century Farmhouse with mountain views

ONTARA....

ONTARA....

1789 Shaker Farmhouse in Berkshires/Hudson Valley

The price is SAR 604
SAR 1,584 total
includes taxes & fees
15 Jan - 16 Jan
1789 Shaker Farmhouse in Berkshires/Hudson Valley

Renovated Berkshires Farmhouse - minutes from hiking, swimming, and Tanglewood

Renovated Berkshires Farmhouse - minutes from hiking, swimming, and Tanglewood

1800s Carriage house in Berkshires / Hudson Valley

The price is SAR 319
SAR 683 total
includes taxes & fees
22 Jan - 23 Jan
1800s Carriage house in Berkshires / Hudson Valley
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Cheshire

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1755)
"I enjoyed my stay here, Thanksgiving weekend, 1st snow, picturesque, comfortable Kitchen is adequate, bathroom had a spa tub that helped take the chill out, heat was on when we entered Laundry machines are available (we did not use them though) We did not try the amenities, pretty much stayed in and enjoyed cooking a small holiday meal in this beautiful setting One thing of note- television in bedroom was not working"
The price is SAR 704
SAR 810 total
includes taxes & fees
22 Jan - 23 Jan
Vacation Village in the Berkshires

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods

Peace and quiet on the lake

9.6 out of 10, Exceptional, (202)
"The house was great with plenty to do in the area. It was warm, comfortable, and just what we were looking for a quick weekend away. Would definitely return.Thanks,-Mike"
Peace and quiet on the lake
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.