Farmstay vacation rentals in Berkshire County

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Popular amenities for Berkshire County farmstay rentals

Family-friendly farm stay rentals

Top guest favorite
A serene view of rolling hills and lush greenery is framed by a foreground of wildflowers and tall grass. The landscape is dotted with trees, and bright clouds drift across a clear blue sky, creating a peaceful outdoor setting.
Home in Cummington
4.9 out of 5 average rating, 111 reviews

Beautiful Secluded Country House

AlisonRating, 5 stars1 month ago
This home is a hidden gem in the woods. It is perfect for large families or groups of couples traveling together. The only negative is actually a positive; the house is situated far from markets and restaurants, but if you like privacy and seclusion, this is your perfect retreat.
Superhost
An old agricultural tool sits in a grassy field, its wheels complementing the expansive landscape. In the background, vibrant hues of sunset illuminate the sky, casting a soft glow over the lush green foliage and distant hills.
Guest suite in Lee
4.74 out of 5 average rating, 197 reviews

Berkshire Charm w/ Panoramic views

KadeeRating, 5 stars8 months ago
Picturesque location! Beautiful and peaceful ! Thanks for a lovely getaway! The WiFi was great and perfect for a day of remote working.
Superhost
The exterior of a renovated antique farmhouse is displayed, featuring a white facade and multiple entrances framed by greenery. A spacious lawn surrounds the house, complemented by mature trees in the background under a clear blue sky.
Home in Lanesborough
4.9 out of 5 average rating, 110 reviews

Elmwood Farmhouse

HannahRating, 5 stars3 weeks ago
Our friend group really enjoyed staying here on a rainy weekend in May. Hanging out by the wood burning stove and doing puzzles at the table was a highlight, and our dog loved being able to be outside on the dog run. The location was fantastic - right in between Lenox and North Adams - so we were able to access museums and hikes easily. Would highly recommend!
Guest favorite
A serene view of the surrounding mountains is captured during sunset, with soft sunlight illuminating the landscape. A grassy area is visible, framed by trees, and a wooden deck extends into the view, creating a peaceful outdoor space.
Home in Hancock
4.88 out of 5 average rating, 49 reviews

Jiminy Peak Peaceful Home in Berkshires

EllenRating, 5 stars4 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 favorite
A spacious living area is highlighted by exposed wooden beams and hardwood flooring. A large sectional sofa faces a rustic fireplace, which is surrounded by logs. Natural light enters through multiple windows, illuminating the cozy ambiance.
Cottage in Becket
4.78 out of 5 average rating, 165 reviews

Tranquil Lake Cottage on 3 Acres with Large Deck

DavidRating, 5 stars1 month ago
Enjoy your stay at this beautiful home. Looking for a get away from everyone this is the place to stay. House was perfect when we arrived and everything was smooth and simple from start to finish!
A comfortable living area features a cozy seating arrangement, accented by a patterned area rug. A white brick fireplace holds a gently crackling fire. Natural light filters through a large window, illuminating a window seat adorned with cushions.
Home in Canaan
4.91 out of 5 average rating, 151 reviews

Orchard House-HudsonValley

KimberlyRating, 5 stars2 weeks ago
Wonderful home and grounds, quaint and eclectic decor. Super comfortable beds and right-at-home warmth. Responsive, friendly hosts!
Guest favorite
An open living space features high wooden ceilings with exposed beams and a stylish pool table positioned at the center. A cozy couch sits nearby, with a staircase leading to a loft area visible in the background. Natural light fills the room through large windows.
Home in Dalton
4.93 out of 5 average rating, 195 reviews

Brooksong, the perfect Berkshires getaway

JoannaRating, 5 stars3 weeks ago
Thank you, Salome, for a wonderful stay. Our extended family felt very relaxed and comfortable in your lovely home. It was a rainy weekend, so it was especially nice that there was a pool table, a fuzeball table, and lots of places in the house to hang out together. The bedrooms and bathrooms were lovely and the shared space was large and inviting. We enjoyed making meals together in the open kitchen. And the neighbor was so picturesque! We loved staying next door to the horses and donkeys, and taking walks on your beautiful farm-filled road. Thanks so much for making our stay such a special weekend. We all hope to ba back again! Very best to you and yours, Joanna and family
A two-story Victorian farmhouse is set on a half-acre lot, surrounded by verdant gardens and trees. The wraparound porch features decorative trim and leads to the front door. Colorful foliage enhances the inviting exterior during the fall season.
Home in Adams
4.93 out of 5 average rating, 247 reviews

1890 House

Wen OngRating, 5 stars3 weeks ago
kate’s home was a cozy and peaceful retreat. she was super responsive, even with our late check-in, and the house had everything we needed to unwind — especially the fireplace, which we used almost every day. the kitchen was well-equipped, and we loved exploring the local food spots and hiking trails nearby. overall, a lovely stay — we’d definitely come back!

Farm stay rentals with a patio

Top guest favorite
A charming exterior of a two-story farmhouse is displayed, featuring a red front door and black-shuttered windows. Lush shrubs flank the entrance, and the surrounding grounds include a manicured lawn and mature trees. The home's siding is white, contributing to its classic aesthetic.
Home in Great Barrington
5 out of 5 average rating, 19 reviews

Elegant 5 Bedroom Farmhouse with expansive lawn

RyanRating, 5 stars5 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!!
Top guest favorite
A firepit area is surrounded by multiple Adirondack chairs, resting on a stone patio. Lush greenery and trees frame the background, with a cozy cabin visible in a clearing. Sky features soft clouds, enhancing the serene outdoor setting.
Cabin in Sheffield
5 out of 5 average rating, 29 reviews

Berkshires Cabin with Stunning Views

KamronRating, 5 stars3 days ago
Amazing place, incredibly clean & an even more incredible view. Loved it!
Superhost
A charming two-story farmhouse is set amidst trees, featuring a green metal roof and white siding. A welcoming front porch is visible, flanked by neatly trimmed shrubs. The inviting landscape includes colorful fall foliage and a well-maintained lawn, enhancing the rural setting.
Home in Hillsdale
4.75 out of 5 average rating, 8 reviews

Farm House with valley view

JosserRating, 5 stars11 months ago
To Mr John it was amazing a Stay with you. Thanks for everything. This place is amazing. Quiet and peacefully.
Guest favorite
The interior space features a white armchair beside a decorative wooden stool and a black coffee table. A tall ladder leads to the lofted area, while a metal shelving unit displays a framed image of a cow and a plant. Exposed wooden beams complement the natural decor.
Home in Egremont
4.91 out of 5 average rating, 82 reviews

Modern and Stylish Country Lakeside Cottage

NikiRating, 5 stars3 weeks ago
This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!
Top guest favorite
An open dining area features a wooden table surrounded by six antique-style chairs. Large windows allow natural light to illuminate the room, which is adorned with colorful rugs and a cozy couch in the adjacent living space.
Home in Otis
5 out of 5 average rating, 26 reviews

4 Bedroom Farmhouse close enough/far enough

PaulRating, 5 stars9 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 favorite
A charming house is set on a spacious green lawn, framed by a wooden fence. Surrounding trees add to the natural landscape, with rolling hills visible in the background. The sky displays a mix of clouds, contributing to a serene atmosphere.
Home in Adams
4.92 out of 5 average rating, 59 reviews

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

StewRating, 5 stars1 week ago
We had two large dinners at Jay's house and it was perfect for hosting 22 people. THe beds were comfortable, there were all the knives and kitchen gadgets we needed to serve dinner to 22 people two nights in a row. The property is beautiful: lush and green.
Top guest favorite
An outdoor deck features a pair of unique swinging chairs and a dining set under a large umbrella. Lush greenery surrounds the area, with a backdrop of tall trees and a manicured lawn. Colorful lawn furniture is visible in the distance, inviting relaxation.
Home in Hancock
4.97 out of 5 average rating, 35 reviews

Berkshire Retreat: Huge Home W/Hot Tub & Yard

KaylaRating, 5 stars3 months 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!
A spacious kitchen features a large wooden island with seating for five. Modern appliances, including a gas stove and coffee station, are positioned among white cabinetry. Natural light floods in through multiple windows, enhancing the bright atmosphere of the inviting cooking space.
Home in New Marlborough
5 out of 5 average rating, 6 reviews

Contemporary Country Farm

VictoriaRating, 5 stars22 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!

Farmstay rentals with a washer and dryer

A private outdoor patio area features two comfortable, light-brown chairs positioned beside a small table. A hot tub is located in the background, while lush green plants frame the space, adding a natural touch to the serene environment.
Home in Pittsfield
4.81 out of 5 average rating, 182 reviews

Beautiful House By The Lake W/Jetted Hot Tub

AndrewRating, 5 stars2 months 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.
Guest favorite
The spacious interior features high wooden beams and a stone fireplace at its center. Natural light fills the area through large windows, highlighting the open floor plan. A loft area is visible above, and comfortable seating arrangements support relaxation and gatherings.
Farm stay in New Lebanon
4.95 out of 5 average rating, 225 reviews

Barn Stay at Shadowbrook Farm

JenniferRating, 5 stars1 month ago
The space was beautiful, clean, and exactly as pictured! We enjoyed a weekend away and appreciated the local recommendations shared in the guide. We spent time exploring the farm, the surrounding area, and also were able to kick back and relax in the amazing property.
Superhost
Cottage in Hillsdale
4.85 out of 5 average rating, 67 reviews

Secluded Country Getaway on 22 acres

JimRating, 5 stars9 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 favorite
Home in Great Barrington
4.96 out of 5 average rating, 49 reviews

River Cottage: Riverfront Home, Walkable Community

JosephRating, 5 stars1 month ago
Great place for a family walking distance to downtown great barrington but still quiet. Fenced in backyard is beautiful and nice for a dog.
Superhost
A bright and airy hallway features white shiplap walls and wooden flooring. Natural light floods the space through skylights and windows. Doorways lead to guest rooms, while a modern light fixture adds a subtle accent to the upper level.
Home in Great Barrington
4.89 out of 5 average rating, 18 reviews

Shimmering Lake Views + Lake Toys!

LindseyRating, 5 stars3 weeks ago
Beautiful home, feels even bigger than the pictures portray. It was exactly what we were looking for, a peaceful stay in a beautiful setting. There were occasional gunshots from the private range across the way but we were aware of this from other reviews and was overall not a bother to us. Only 10 minutes drive to the town of Great Barrington which had a lot of lovely shops and restaurants. Weather was not really conducive to using the paddle boards and kayaks but otherwise we had a lovely time!
Top guest favorite
A modern bathroom is showcased, featuring a glass-enclosed shower with a rainfall showerhead. Dark cabinetry complements the light-toned tile walls. A marble vanity with contemporary fixtures is positioned beside a wall-mounted mirror, creating a clean and functional space.
Home in Adams
4.99 out of 5 average rating, 78 reviews

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

TejalRating, 5 stars2 weeks ago
We rented Amar's place for a 3 day getaway to enjoy the Berkshires area. We had 7 adults in our party and found Amar's place to be perfect for our needs. It's a beautiful home in a quiet town with all the amenities that one would hope for. Amar was extremely responsive and even proactive with communication and was a very gracious host. I would highly recommend his place
Guest favorite
A bright and airy sunroom features large screened windows providing expansive views of lush green mountains and the sky. Two wooden rocking chairs are positioned on the deck outside, inviting relaxation while enjoying the surrounding natural beauty.
Home in New Lebanon
4.98 out of 5 average rating, 60 reviews

Berkshire Mountain home views, pool, Queechy Lake

GeorgeRating, 5 stars3 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
A charming white farmhouse is framed by a decorative white gate adorned with greenery. A pebbled pathway leads to the entrance, surrounded by a well-kept lawn and trees that create a serene, inviting atmosphere.
Guesthouse in Lee
4.84 out of 5 average rating, 37 reviews

1815 Modern Farmhouse : 3min to Stockbridge

JanetteRating, 5 stars2 weeks ago
Abigail is a very accommodating host! She is very responsive, friendly and professional. Abigails home is clean, well furnished and very comfortable. We will stay again should we find ourselves in the area in the future!

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