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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 24 Farmstay in Pittsfield with updated reviews, rates, and availability.

18th century Berkshires farmhouse on 12 acres, impeccably updated.
Exterior

18th century Berkshires farmhouse on 12 acres, impeccably updated.

18th century Berkshires farmhouse on 12 acres, impeccably updated.
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
Charming Farmhouse - quiet, private & peaceful
Beautiful stone walls

Charming Farmhouse - quiet, private & peaceful

9.6 out of 10, Exceptional, (64)
"The house was perfect for our needs. A winter snow storm brought even more beauty to the outside view. Looking forward to returning on another trip to visit our son and his family."
Charming Farmhouse - quiet, private & peaceful
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 AED 393
AED 746 total
includes taxes & fees
23 Feb - 24 Feb
NEW RENO - Historic Loft w/views of the Berkshires
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!
Escape to this 120-acre farm in Upstate NY! Pet friendly.
A winter wonderland!

Escape to this 120-acre farm in Upstate NY! Pet friendly.

The price is AED 1,690
AED 2,695 total
includes taxes & fees
23 Feb - 24 Feb
Escape to this 120-acre farm in Upstate NY! Pet friendly.
Modern Victorian - 2.5hrs from NYC - 100acres - Nature- Country living
Exterior

Modern Victorian - 2.5hrs from NYC - 100acres - Nature- Country living

10.0 out of 10, Exceptional, (4)
"The setting was pleasant and bucolic . . . the farm house has a huge porch covering two sides of the house that is lovely to sit on with a morning cup of coffee or evening drinks with friends. Everything was extremely clean and ordered in the home. Communication with the owners was also clear and helpful . . . lovely time."
Modern Victorian - 2.5hrs from NYC - 100acres - Nature- Country living
Berkshire Rural Retreat
Private kitchen

Berkshire Rural Retreat

10.0 out of 10, Exceptional, (21)
"We had a very nice stay over the New Year’s holiday. The house was clean, comfortable and cozy. The host was responsive as well. "
Berkshire Rural Retreat
Farmhouse on Otis Pond
Exterior

Farmhouse on Otis Pond

10.0 out of 10, Exceptional, (1)
"We had a wonderful time at the farmhouse. It is a charming old home. Our son loved being able to wake up and go fishing. The owner quickly responded to any questions. I loved sitting on the porch swing and listening to the birds."
Farmhouse on Otis Pond
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.
Private Unit in shared 1830 Farmhouse
Exterior of home and entry

Private Unit in shared 1830 Farmhouse

2.0 star property
Private Unit in shared 1830 Farmhouse
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!
NEW RENO - Chalet-style farm loft near Tanglewood
Room

NEW RENO - Chalet-style farm loft near Tanglewood

The price is AED 275
AED 624 total
includes taxes & fees
28 Feb - 1 Mar
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 AED 591
AED 1,550 total
includes taxes & fees
23 Feb - 24 Feb
1789 Shaker Farmhouse in Berkshires/Hudson Valley
1800s Carriage house in Berkshires / Hudson Valley
Exterior

1800s Carriage house in Berkshires / Hudson Valley

The price is AED 312
AED 661 total
includes taxes & fees
23 Feb - 24 Feb
1800s Carriage house in Berkshires / Hudson Valley
Charming 5-bedroom farmhouse with AC, WiFi in delightful Ghent
Exterior

Charming 5-bedroom farmhouse with AC, WiFi in delightful Ghent

The price is AED 1,102
AED 1,961 total
includes taxes & fees
23 Feb - 24 Feb
Charming 5-bedroom farmhouse with AC, WiFi in delightful Ghent
New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge
Exterior

New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge

2.0 star property
10.0 out of 10, Exceptional, (6)
"We recently rented this house for two weeks in order to spend time under the same roof with our grown children and baby grandson - and we couldn't have had a more enjoyable time! The house provided ample space for us to gather in small groups or larger ones whether we were indoors, outside on the deck or in the yard. The location in town was ideal for pushing the baby stroller along all the sidewalks as well as easily accessing all the shops and restaurants. With the Red Lion Inn only a block...
New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge
Charming 3-bedroom farmhouse with WiFi, central air in lovely Ghent
Room

Charming 3-bedroom farmhouse with WiFi, central air in lovely Ghent

Charming 3-bedroom farmhouse with WiFi, central air in lovely Ghent
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
10 Minutes to Ski Butternut! Dogs Welcome!
Interior

10 Minutes to Ski Butternut! Dogs Welcome!

10 Minutes to Ski Butternut! Dogs Welcome!
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 Pittsfield

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Great Room with pull out doble sleeper sofa that sleeps 2

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (139)
"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
View from the lawn by the water

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (55)
"Perfect lake front home to get away for a quick weekend trip with the family over the holidays!! Location, location location, close proximity to downtown Pittsfield, 15 from Jiminy peak & Bousquet Mt. Andrey was extremely helpful throughout the process with suggestions for food and activities for the kids. The house was a perfect fit for our family and friends. Everyone enjoyed their time there and would definitely book again"
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Hancock Village Inn at Jiminy Peak
Hancock Village Inn in Winter

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (9)
"Annual mother/son ski and food fest!Lots of fun with family and friends. Plenty of space for everyone.. Kitchen wascwell"
The price is AED 2,196
AED 3,898 total
includes taxes & fees
25 Feb - 26 Feb
Hancock Village Inn at Jiminy Peak
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.