
Farmstay vacation rentals in Berkshire County
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Top-rated farmstay rentals in Berkshire County
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Popular amenities for Berkshire County farmstay rentals
Family-friendly farm stay rentals

Beautiful House By The Lake W/Jetted Hot Tub
Our stay was excellent. House was exactly as advertised and fit our needs perfectly. We were a large group including young children and everyone had plenty of space both for sleeping and recreation. Kitchen was well stocked with anything you needed to cook your meals. Host was responsive and very clear with instructions and answering questions. 5/5 stars. Would highly recommend. A quick note for future guests. If the weather is cold the kitchen floor gets cold. Would recommend packing slippers.

Berkshire Charm w/ Panoramic views
Picturesque location! Beautiful and peaceful ! Thanks for a lovely getaway! The WiFi was great and perfect for a day of remote working.

Jiminy Peak Peaceful Home in Berkshires
We had a great stay at Michelle’s place. It was very conveniently located to the base of Jiminy Peak, which made getting to and from the mountain very easy. The house was very well appointed and had everything we needed. We used the fireplace twice and it was super easy. Having access to the facilities at The Country Inn at Jiminy Peak was great as I am injured and can’t ski currently, so instead I went to the gym each day. My family didn’t want to leave and my kids are asking when we can go back!

Tranquil Lake Cottage on 3 Acres with Large Deck
We had a wonderful long weekend at Michelle’s place. We woke to 8 inches of snow in April, so made good use of the fireplace. We enjoyed exploring the area, found several fun places to ride our mountain bikes and showed our daughter another part of Massachusetts away from her college.

Orchard House-HudsonValley
We had great stay! We have family that lives just down the street, so the location was perfect for our needs. The house easily accommodated our family of 6. It is set up for hanging out with plenty of everything you need for cooking and entertaining. The beds were very comfortable and sharing the 2 bathrooms/showers worked out just fine. We will be back!

Brooksong, the perfect Berkshires getaway
What a perfect place for two families to get together. Beautiful waconah forest just next door. Nice, peaceful place

Modern Farm House 5 minutes from Great Barrington
Perfect place for a getaway, loved everything about this cozy home and just a few minutes away from excellent skiing. Will definitely return again!

1890 House
This house was lovely for post-holiday rest and relaxation! It’s so cozy and well-equipped—we felt right at home. Thanks for hosting us!
Farm stay rentals with a patio

Berkshires Cabin with Stunning Views
Awesome location! Great views! Very cozy and comfortable! 10/10 stay.

Elegant 5 Bedroom Farmhouse with expansive lawn
Just had a great stay in Great Barrington. Enjoyed the house and all of its amenities. Location was great, close to great restaurants, hiking and skiing. Would recommend this property and our host!!

Farm House with valley view
To Mr John it was amazing a Stay with you. Thanks for everything. This place is amazing. Quiet and peacefully.

Modern and Stylish Country Lakeside Cottage
fantastic and cozy, nice backyard, well equipped with amenities as well

Mount Greylock View Retreat,3 bedroom,2 1/2 bath.
Great, private, peaceful and cozy. Close enough to town to find things to do but you can also stock the kitchen with groceries and stay in and not need to leave. Primary bedroom is large a cozy, comfortable mattress and linens. Enjoyed the tub both days and water gets nice and hot. Loved that we could bring all 3 little doggos and they loved running around the yard. Will be back when the warm weather hits!

Berkshire Retreat: Huge Home W/Hot Tub & Yard
John was the best host! He was super responsive and the photos/ description were spot on! Had a great weekend there and only a 4 minute drive to Jiminey Peak! Definitely will stay again!

Contemporary Country Farm
Our stay was incredibly relaxing… after sunsets and star gazing the peaceful sounds of nature sang us to sleep. The kitchen was clean and well equipped for us to make a great family meal. The bedding is comfortable and clean so everyone had a restful nights sleep. Be sure to enjoy the outdoor shower!

Scenic 3BDRM Farmhouse - Modern Updates/EV Charger
Stayed with my best friends from Hotchkiss as a little sweet reunion—adorable house, super clean, and fantastic location. The sweet Williams pastries for breakfast were the sweetest touch! Really a wonderful place to stay.
Farmstay rentals with a washer and dryer

Barn Stay at Shadowbrook Farm
This was our second stay, and we will be going back again and again. The barn is gorgeous, as is the entire property. We love to cook in that beautiful kitchen as we enjoy the fireplace. Perfect relaxing getaway for us!

River Cottage: Riverfront Home, Walkable Community
We enjoyed a relaxing weekend in Great Barrington at this great house. We loved walking a few minutes into town for coffee from our choice of cafes and appreciated how many shops and restaurants we could access without needing to drive. The house was comfortable and clean and the kids loved playing in the big backyard while the snow was coming down - a quintessential Western MA experience!

Secluded Country Getaway on 22 acres
I cannot thank Joyce enough for opening her lovely home to us. We felt relaxed and refreshed from the minute we arrived. Whether it was sipping coffee and reading by the pond or watching our beagle explore the grounds, I don't think the smile left my face. Joyce was so helpful with recommendations and available to answer any questions we might have had. The proximity to Great Barrington and Stockbridge was fantastic but the local Hillsdale attractions should be missed. We'll absolutely stay here again! Love this house.

Little House in the Woods by Evergreen Home
We had a lovely stay in this home and hope to come back! Even though we arrived late in the evening, the host provided detailed instructions and made it very easy to check in. The house was very clean and had everything that we needed. It is such a peaceful place - we especially loved the screened-in porch. We wish we could have stayed longer. Thank you for your hospitality!

Mountain Escape - hike, bike, museums, and more!
The home is in a great location - middle of town but feels very private and quiet. Well-appointed and kitchen was very functional. House was very comfortable and has a lot of character. Amar was very communicative from the booking until we left. When we had a small issue he responded immediately and it was easily resolved. Beds were comfortable and the entire place was very clean. We really enjoyed our stay!

Berkshire Mountain home views, pool, Queechy Lake
The house was very spacious, the kids ranging from 6-10 loved the games, especially cue ball and fuzz ball. The adults loved the fact there was a lower half where the kids can watch movies and play, while the adults did grown up chatting in the living space. A memorable ski weekend that everyone enjoyed to the fulliest and sad it went so fast. We look forward returning one day in the spring or summer to see a different aspect of the area. Thank you!

1815 Modern Farmhouse - 3min to Stockbridge
Abigail and Paulo’s attention, responsiveness and caring about their guests makes your visit to a wonderful place much more wonderful and much more comfortable.

Family Fun at Hygge House on Richmond Pond
The Hygge House was a lovely spot to spend my birthday weekend with my family and friends. We took advantage of so many close-by activities. But the highlights were at the house itself - paddling the canoe and kayak through the water, outdoor dinner, and s’mores at the fire pit. Jessica was also so easy to communicate with and super accommodating during a personal emergency we experienced. We loved our stay and would love to come back again soon.
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- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Berkshire East Mountain Resort
- Six Flags New England
- Taconic State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Bushnell Park
- Mount Sugarloaf State Reservation
- Opus 40
- John Boyd Thacher State Park
- Mount Greylock Ski Club
- Hartford Golf Club
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Mount Snow Ski Resort
- Bash Bish Falls State Park
- Beartown State Forest
- Otis Ridge
- Norman Rockwell Museum
- Naumkeag
- Bright Nights at Forest Park
- Rockledge Golf Club
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