Farmstay vacation rentals in Berkshire County

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Popular amenities for Berkshire County farm stay accommodations

Family-friendly farm stay accommodations

Home in Pittsfield
4.82 out of 5 average rating, 180 reviews

Beautiful House By The Lake W/Jetted Hot Tub

AndrewRating, 5 stars1 month ago
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.
Superhost
Guest suite in Lee
4.74 out of 5 average rating, 197 reviews

Berkshire Charm w/ Panoramic views

KadeeRating, 5 stars6 months ago
Picturesque location! Beautiful and peaceful ! Thanks for a lovely getaway! The WiFi was great and perfect for a day of remote working.
Guest favourite
Home in Hancock
4.88 out of 5 average rating, 48 reviews

Jiminy Peak Peaceful Home in Berkshires

EllenRating, 5 stars2 months ago
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!
Guest favourite
Cottage in Becket
4.78 out of 5 average rating, 163 reviews

Tranquil Lake Cottage on 3 Acres with Large Deck

SarahRating, 5 stars2 weeks ago
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.
Home in Canaan
4.91 out of 5 average rating, 150 reviews

Orchard House-HudsonValley

JeeyuneRating, 5 stars3 months ago
Huong’s place was very well-maintained, clean, cozy and spacious. She also responded to our queries quickly and also kindly provided a complimentary drink. The location was perfect for us, situated in great proximity to two ski resorts that we went to (Catamount and Jiminy). We had a lovely stay and would highly recommend it to others!
Guest favourite
Home in Dalton
4.93 out of 5 average rating, 192 reviews

Brooksong, the perfect Berkshires getaway

GinniRating, 5 stars2 weeks ago
What a perfect place for two families to get together. Beautiful waconah forest just next door. Nice, peaceful place
Guest favourite
Home in Egremont
4.94 out of 5 average rating, 279 reviews

Modern Farm House 5 minutes from Great Barrington

GinaRating, 5 stars2 weeks ago
Elle’s place was beautiful and well located for a long weekend away from Boston. She was responsive and friendly. Would recommend!
Home in Adams
4.93 out of 5 average rating, 246 reviews

1890 House

RachelRating, 5 stars16 months ago
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 accommodations with a patio

Top guest favourite
Cabin in Sheffield
5 out of 5 average rating, 28 reviews

Berkshires Cabin with Stunning Views

JohnRating, 5 stars1 month ago
Awesome location! Great views! Very cozy and comfortable! 10/10 stay.
Top guest favourite
Home in Great Barrington
5 out of 5 average rating, 19 reviews

Elegant 5 Bedroom Farmhouse with expansive lawn

RyanRating, 5 stars4 months ago
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!!
Superhost
Home in Hillsdale
4.75 out of 5 average rating, 8 reviews

Farm House with valley view

JosserRating, 5 stars10 months ago
To Mr John it was amazing a Stay with you. Thanks for everything. This place is amazing. Quiet and peacefully.
Guest favourite
Home in Egremont
4.94 out of 5 average rating, 78 reviews

Modern and Stylish Country Lakeside Cottage

SeanRating, 5 stars1 day ago
Hello - Great to be back in Maureen's home. Super excellent location 5mins or so to Great Barrington and close to everything the Berkshires has to offer. Home is really amazing for a romantic weekend away, my partner and I both loved everything about the home and the surrounding property. no notes.
Top guest favourite
Home in Otis
5 out of 5 average rating, 26 reviews

4 Bedroom Farmhouse close enough/far enough

PaulRating, 5 stars8 months ago
We spent a wonderful month at Julie’s farm house in West Otis. The house itself was lovely, comfortable, welcoming. We especially enjoyed the kitchen (larger than you’d think from the photos and very well-stocked) and the deck, where we spent most of our time. There was plenty of room for our guests as well, including our grown kids and two small dogs. We all loved walking on the path from the house to the road further on, and the feeling we got from being surrounded by nature. Julie and Shikhar were fabulous hosts. There were thoughtful touches in the house when we arrived – some snacks, coffee, fresh flowers – and we were lucky to share in some of the bounty from Julie’s garden. Julie communicated with us regularly, offering suggestions for meals or culture, and responding quickly to questions. Though the house is close to the renovated barn where Julie and Shikhar live, we had as much privacy as we wanted or needed. Thanks to both of you and we look forward to a return visit.
Guest favourite
Home in Adams
4.91 out of 5 average rating, 57 reviews

Mount Greylock View Retreat,3 bedroom,2 1/2 bath.

MeghanRating, 5 stars1 month ago
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!
Top guest favourite
Home in Hancock
4.97 out of 5 average rating, 35 reviews

Berkshire Retreat: Huge Home W/Hot Tub & Yard

KaylaRating, 5 stars1 month ago
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!
Home in New Marlborough
5 out of 5 average rating, 6 reviews

Contemporary Country Farm

VictoriaRating, 5 stars20 months ago
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!

Farm stay rentals with a washer and dryer

Guest favourite
Farm stay in New Lebanon
4.95 out of 5 average rating, 222 reviews

Barn Stay at Shadowbrook Farm

AbbyRating, 5 stars3 weeks ago
my friend and I stayed at Shadowbrook Farm to do an art retreat together, and it was perfect. it has a large table and a ton of seating which allowed us to spread out. we much enjoyed the antique farm implements used to decorate the place. it's gorgeous!
Guest favourite
Home in Great Barrington
4.96 out of 5 average rating, 47 reviews

River Cottage: Riverfront Home, Walkable Community

MikeRating, 5 stars3 months ago
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!
Superhost
Cottage in Hillsdale
4.85 out of 5 average rating, 67 reviews

Secluded Country Getaway on 22 acres

JimRating, 5 stars8 months ago
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.
Guest favourite
Home in Sheffield
4.97 out of 5 average rating, 72 reviews

Little House in the Woods by Evergreen Home

MinRating, 5 stars10 months ago
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!
Top guest favourite
Home in Adams
4.99 out of 5 average rating, 72 reviews

Mountain Escape - hike, bike, museums, and more!

NodiraRating, 5 stars1 week ago
Amar was an amazing host and we greatly enjoyed staying in his place! He was very accommodating and responsive. He purchased a toddler crib for our stay, which was really nice of him! The house was clean, kids friendly and had everything that we needed.
Guest favourite
Home in New Lebanon
4.98 out of 5 average rating, 59 reviews

Berkshire Mountain home views, pool, Queechy Lake

GeorgeRating, 5 stars2 months ago
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!
Superhost
Guesthouse in Lee
4.83 out of 5 average rating, 36 reviews

1815 Modern Farmhouse - 3min to Stockbridge

MartyRating, 5 stars9 months ago
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.
Guest favourite
Home in Pittsfield
4.95 out of 5 average rating, 62 reviews

Family Fun at Hygge House on Richmond Pond

KatrinaRating, 5 stars7 months ago
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.

Destinations to explore