Photo by Ed Gaffny

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Compare 16 Farmstay in Cheshire with updated reviews, rates, and availability.

Charming Farmhouse - quiet, private & peaceful
Beautiful stone walls

Charming Farmhouse - quiet, private & peaceful

9.6 out of 10, Exceptional, (60)
"The property was great, and the owner was super responsive. I would definitely rate this property excellent if it was a little cleaner. Loved the quiet and peacefulness! "
Charming Farmhouse - quiet, private & peaceful
Modern Country Farmhouse, Walking Distance to Lake
Exterior

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!
Property grounds

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!
Large, family-friendly farmhouse located in the beautiful Berkshires
Exterior

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.
Property grounds

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
Room

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
Super discount for 9/23 to 10/3. Fun fairs, flea markets, music and hikes.
Renovated, landscaped, furnished and ready for guests.

Super discount for 9/23 to 10/3. Fun fairs, flea markets, music and hikes.

9.8 out of 10, Exceptional, (10)
"Perfect place for our family for a weekend wedding in the area. Comfortable picturesque and very clean."
Super discount for 9/23 to 10/3. Fun fairs, flea markets, music and hikes.
Historic 1817 Berkshire Farmhouse- Close to Everything!
Our sun-filled kitchen stocked with basic cooking supplies. Original wood beams.

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
Private kitchen

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
Restored historic farmhouse on 25 private acres
Front of House

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
The East side facing the street

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
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Exterior detail

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NEW RENO - Chalet-style farm loft near Tanglewood
Room

NEW RENO - Chalet-style farm loft near Tanglewood

The price is SAR 282
SAR 646 total
includes taxes & fees
25 Nov - 26 Nov
NEW RENO - Chalet-style farm loft near Tanglewood
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Exterior

1789 Shaker Farmhouse in Berkshires/Hudson Valley

The price is SAR 604
SAR 1,592 total
includes taxes & fees
25 Nov - 26 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Renovated Berkshires Farmhouse - minutes from hiking, swimming, and Tanglewood
Living area

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

Renovated Berkshires Farmhouse - minutes from hiking, swimming, and Tanglewood
NEW RENO - Historic Loft w/views of the Berkshires
Living area

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 781 total
includes taxes & fees
25 Nov - 26 Nov
NEW RENO - Historic Loft w/views of the Berkshires
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
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1746)
"Property was beautiful, great staff "
The price is SAR 634
SAR 733 total
includes taxes & fees
26 Nov - 27 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is SAR 559
SAR 614 total
includes taxes & fees
26 Nov - 27 Nov
Jiminy Peak Mountain Resort
Pristine Home In Becket Woods

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
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.