
Farmstay vacation rentals in The Berkshires
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Top-rated farmstay rentals in The Berkshires
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Family-friendly farm stay rentals

Light-filled guest cottage
An incredibly charming, rustic, simple and comfortable small cottage, in a gorgeous rural setting. Just as advertised. It was perfect. Right across the road is Tivoli Bays, with beautiful trails for walking and hiking, and a small waterfall too. If you like, it's just a short walk to Broadway, the main strip in the village of Tivoli. You'll find a few restaurant options, a small market, sandwich shop, excellent coffee, and homemade ice cream. I met Yuko who couldn't be nicer and was a pleasure to chat with. A great experience all around - highly recommend booking a stay!

Casa Bella Vista with Great Views!
We had a wonderful stay at this house! It’s very spacious, spotless, and well-equipped with everything you need. The property is large and beautiful, with stunning views and even a pond on-site. Everything is convenient and thoughtfully arranged — from the cozy fireplace to the overall peaceful atmosphere. The place feels both comfortable and private. I’ve already recommended it to my friends and would love to come back again. Truly a perfect getaway in nature!

Everything on one floor 2 Bdrm/1.5 Bth & Pets Ok
The best Airbnb we’ve ever stayed at! It truly felt like home—every detail was so thoughtfully taken care of. You have everything you need for a comfortable stay, from a well-stocked space to those little touches that make a big difference. The bed and pillows were super comfortable, and even though it rained, the hosts had dry firewood ready for the fireplace, which made it feel extra warm and inviting. We loved sitting by the lake and even saw a fish jump out of the water—such a magical moment! Communication with the host was excellent from start to finish. And thank you so much for approving our cats to stay with us—it meant the world. If we could give 10 stars, we absolutely would. Highly recommend this place to anyone looking for a peaceful and welcoming getaway. Thank you for an unforgettable stay!

Hudson Valley Cottage
This was so charming & cozy, while also being conveniently close to nature nails & downtown Woodstock. We thoroughly enjoyed our stay & would recommend!

Stone School Cottage
This is a unique and special stay. From the very first interaction, Rich was very responsive and kind in his communications. The property is well cared for and very welcoming. The school room on the main floor is accessible and open to children playing - lots of books and toys. The living space upstairs was large, yet cozy. Stocked with all the things someone might need during their stay. It was so quiet at night, and filled with birdsong in the morning. My young nephews visited in the mornings (Rich was totally okay when I asked him) and they loved "my house." The farm adjacent to their property has alpacas and mini-horses that loved to crunch up the carrots we fed them (provided by Rich). The hosts have honored the history of the one-room school house, while making a fun and very enjoyable place to stay. Highly recommend!
Flamig Farm Staycation
What an awesome and unique air B&B! The space is comfortable and very quiet in the evenings and night. It is well outfitted for a family and the farm was lots of fun; we discovered our little one loves chickens. Thanks for sharing a cool experience at your farm. Highly recommended.

19th c. Barn in The Berkshires
Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.

Modern Farm House 5 minutes from Great Barrington
We can't say enough good things about Elle's lovely renovated farmhouse! It's a charming, spotless home, and was the perfect size for the four of us. The furniture was comfortable, the kitchen had wonderful appliances and all the cookware we could possibly need, modern bathrooms with plenty of towels and so on! And what a great location—it’s on a lovely road that’s about a ten minute drive to Great Barrington. We had a few questions for Elle and she responded very quickly. We’ve been to the Berkshires many times and this is without a doubt one of our favorite homes. We ook forward to staying here again!
Farm stay rentals with a patio

Luxury mountainside cabin sauna + hot tub
Very clean house and comfortable bed. We enjoyed the amenities and making fires. Our dog loved running around the property and we enjoyed being close to town for grocery shopping, cafe access, and hiking trails nearby.

The Farmhouse
This was a gorgeous place with beautiful furnishings, warmth and charm! We will travel out of our way for a revisit. Very highly recommended!

Spacious cabin w/grill, firepit & mountain views
This place is absolutely beautiful, it was a nice weekend escape for our family. Jesse was responsive and helped us be able to plan a surprise for my wife. She loved it

Modern Catskills Cabin
We love Mark and Lori’s properties, so much so this is our 4th year staying with them, the location is great, plenty of outdoor activities close by, great food and drink options close by, the cabin is well equipped for a comfortable stay and the outdoor area is amazing for chilling around a fire. Highly recommend, we already have another stay booked later this year with them.

Modern Luxurious Tiny Home with Private Sauna Spa
We had a delightful two-day stay at this cabin, which offered a perfect blend of comfort and tranquility. The cabin was impeccably clean, thoughtfully organized, and well-equipped with everything we needed. We particularly enjoyed unwinding in the sauna, savoring our meals outdoors, and grilling steaks over the firepit. These moments made our getaway truly memorable.

Lux OffGrid Oasis - A frame Farm + River + Animals
Absolutely beautiful stay! Looks just like the pictures if not better! Gentlemen down the street was so nice and helped us come make a fire when we couldn’t get one started. Couldn’t recommend this place enough if ur looking for a cozy stay! Courtney was great to communicate with also and left a cute hand written note for us upon arrival. We will be back!

Panoramic Mountain View Agri-Cabin
This is a lovely cabin, very cozy and nicely decorated. Beautiful surroundings and the view amazing. It was easy to check in and we were greeted with cookies and eggs from the farm up the road. Very nice! And we loved the little kids play nook! Communication with the host was great and she was very responsive. The two beds were comfortable but the futons were not. We had to have the kids sleep on the two futons due to the size of our group and thought it would be ok but I don't think those futons should be considered for sleeping. They were very hard and the surface was not even. Other than that, we had a lovely stay and would recommend this cabin.

Nestled in Nature
Amazing. Came for a staycation in peaceful environment, we got exactly what we came for. The host was very responsive and communicative.
Farmstay rentals with a washer and dryer

Cleveland House - renovated Berkshires' gem.
We had a wonderful stay at this beautiful home. The beds were extremely comfortable, the house was clean and the kitchen was well stocked. The hosts were very responsive and kind and went above and beyond to make sure we had a great stay. The kids in our group were happy with the toys that were available for them. We would highly recommend staying here for group gatherings. We had a lovely cozy weekend and are so grateful to the hosts!

midcentury mod * POOL * walk out trail to mohonk
The house met all expectations everything is stylishly done, and the host is incredibly responsive and helpful 🤍

Modern & Chic Log Home-Spectacular Mountain Views!
Had a beautiful stay with my parents and sibling -- we loved watching movies on the large projector, cooking meals together in the lovely kitchen and taking in the serenity of the area. Michael was very responsive, and we couldn't have asked for a more pleasant stay in the Catskills!

Refined, serene and like no other, Marlboro, VT.
Jill and T. were amazing hosts, quite possibly the nicest and all around best that I've experienced. They were attentive and incredibly kind, and together have a presence to them that makes you feel comfortable and right at home. They also were a wealth of knowledge about the surrounding area, the property, and the trails that are accessible right down the road from the guest house. The guest house itself is across the large driveway from the main house, and while close, it feels properly secluded and private. Inside, it is impeccably furnished with the styling and taste that only someone well traveled could do so well: books about sculptors, poetry, classics, Vermont history. Beautiful furniture and an inviting layout of the space. The furnishings, books, kitchen setup, and many places to sit and relax, were as much part of the greatness as the nature surrounding it. I will absolutely come back here for the relaxation, the amenities, and also the lovely hosts.

Lakefront +pets +skiing +bbq +firepit +games
We had a great time, the location is great, right on the water and the fishing was even better. A very quiet lake and much bigger when you are out on it in the kayaks. I would surely stay here again!

Hot tub with stunning views, 5 min to Woodstock
Substantial and comfortable space. Very well appointed property with hot tub, bath and kitchen with clothes washing facility. Great views and well located near some lovely towns. We had a big car and parking was slightly tight to turn but a very minor observation!

Litchfield County Farmhouse with a Modern Twist
Wow! This home was such a “wow”—just perfection. The location is spectacular (peaceful and beautiful) and the home was everything you could ask for (a work of art, comfortable, functional, family friendly). We were in town for our son’s graduation from The Woodhall School and Scott’s home was the cherry on top of a perfect weekend. Highly recommend!

Nature Cottage w/ Private Path to River Access
This house was perfect for us (5 friends gathering to fish the Housatonic). Simple, clean, ac/heat/wood-burning stove, all the amenities, and a great hot shower! We were up and down the short path to the river the whole weekend. Amy was a super-host. Attentive when we needed her, but not intrusive. Thanks Amy, we enjoyed our stay!
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