Vacation rentals in The Berkshires

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Popular amenities for The Berkshires vacation rentals

Cabins in The Berkshires

Guest favorite
Cabin in Wurtsboro
4.97 out of 5 average rating, 331 reviews

Spring Spa on a Cascading Brook - The Water House

IrinaRating, 5 stars1 week ago
Amazing plaice. If you are looking for a place fulfilled with serenity, joy and nature, this is a place to go. The house made with love, clean and big. The creek and sounds of water with the fire pit meditative. The hot jacuzzi on the creek is relaxing and fun. The owners are nice people, very orginized and quickly responding to any conserns you migjt have. Walks on the nature is available. We will be back!!! Thank you James and Erene!!
Top guest favorite
Cabin in Cummington
4.98 out of 5 average rating, 213 reviews

Just Be Cabin

HeidiRating, 5 stars2 weeks ago
This is my third stay with Stacey at the Just Be cabin and it’s always lovely. It’s a simple, clean, quiet spot that’s perfect for recharging in the evenings during a working weekend with lots of people-ing! The wood stove was a luxurious amenity on my latest, chilly trip!!
Superhost
Cabin in Clarksburg
4.9 out of 5 average rating, 279 reviews

Mountain Cottage Spectacular Views

AlexRating, 5 stars6 months ago
Ethan and Debora were very communicative and accommodating hosts. The cottage and its views are exactly as stunning as they look. We stayed during a very cold weekend, and they were very proactive about getting the place nicely warmed up for us before our arrival. Terrific spot for a peaceful weekend!
Superhost
Cabin in Plainfield
4.92 out of 5 average rating, 170 reviews

Peaceful Cabin in the Woods

JeanneRating, 5 stars3 days ago
Chris's place is a beautiful cabin nestled in the woods, with birds singing, beautiful airy feel to the cabin, roomy, lovely second floor, most comfy bed I've ever slept in. Loved the colors - wood, tall glass windows and skylights, dark green comforters and pillow covers. It's up a dirt road, neighbors are far away, so if you don't like remote, this isn't your place. But if you do, it's perfect!
Guest favorite
Cabin in New Milford
4.95 out of 5 average rating, 171 reviews

Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit

VanessaRating, 5 stars5 days ago
This place the atmosphere the surroundings it was all so lovely and needed, the price paid off. I loved the views the water and the shower outside. The bed was so comfortable very clean the place overall was very comfy I felt so comfortable. I recommend this place for a stay if you love to be away from people and need calmness. Everything was on spot from the house, the area outside to everything included. Thankyou so much for this, 10/10
Top guest favorite
Cabin in Petersburgh
4.93 out of 5 average rating, 235 reviews

Cozy Retreat in the Trees

AmandaRating, 5 stars1 week ago
A truly magical experience to live in the trees. Igor’s place was a warm and cozy place actually nestled amongst the trees. Any view looked out into the trees and even on a rainy weekend, we enjoyed the sounds, the smells, and all the nature that surrounded us. We even got to use the wood stove which helped keep the chill outside. (Thank goodness all those skills came back to me from childhood) Thank you so much for hosting us and we highly recommend to all.
Superhost
Cabin in Rhinebeck
4.89 out of 5 average rating, 380 reviews

Sunset Bungalow-Mt views on 130acre forest & falls

GailRating, 5 stars3 weeks ago
Beautiful, quiet setting, lovely furniture, all the amenities. Clean and comfortable, and a short drive to shops, restaurants, and hiking trails.
Guest favorite
Cabin in Kerhonkson
4.98 out of 5 average rating, 396 reviews

Zink Cabin | Mountain Views w/ Hot Tub

SeanRating, 5 stars2 weeks ago
We had such a lovely stay at the Zink cabin! The cabin was small but had everything we needed, and was extra-cozy. I was worried it would be cold, but the automatic fireplace worked like a charm and added such a nice cozy touch. The kitchen impressed us with the Nespresso machine and the modern cutlery and cookware. The hot tub and fire pit worked well and gave our weekend that relaxing luxe vibe, which is exactly what we were hoping for. My only comments would be that the road getting up to the cabin had a ton of huge potholes, and I just have a small sedan, so was a bit uneasy about that. The cabin is also very modern and automated, so finding the specific light switches, or learning how the Alexa controlled things took a slight learning curve. But overall, we had a very relaxing, comfortable, and cozy stay and would absolutely stay there again.

Homes in The Berkshires

Top guest favorite
Home in New Paltz
4.98 out of 5 average rating, 489 reviews

midcentury mod * POOL * walk out trail to mohonk

EleonoraRating, 5 stars2 weeks ago
The house met all expectations everything is stylishly done, and the host is incredibly responsive and helpful 🤍
Guest favorite
Home in Woodstock
4.94 out of 5 average rating, 338 reviews

Woodstock Historic Artist Estate - The Pond House

CodyRating, 5 stars1 month ago
No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.
Guest favorite
Home in East Haddam
4.95 out of 5 average rating, 220 reviews

Romantic Getaway at The Lake!

JessicaRating, 5 stars1 week ago
We had an amazing stay! The location was amazing and the hot tub was perfect! Lots of fun activities to do in the area as well and Marissa gave so many great recommendations. My husband and I had a great time !
Guest favorite
Home in Copake
4.96 out of 5 average rating, 194 reviews

Lakefront +pets +skiing +bbq +firepit +games

MelanieRating, 5 stars1 month ago
We had a wonderfully relaxing stay at Frank’s beautiful home! The house was spotless, well-equipped, and had everything we could have needed for a comfortable visit. We especially enjoyed the easy access to the lake and the close proximity to great hiking trails. It was the perfect spot to unwind and connect with nature. We would love to come back again soon!
Superhost
Home in Cheshire
4.85 out of 5 average rating, 214 reviews

19th c. Barn in The Berkshires

JohnRating, 5 stars6 months ago
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.
Guest favorite
Home in Hunter
4.95 out of 5 average rating, 146 reviews

Modern House with Mountain View @Getawind

LindseyRating, 5 stars1 week ago
We loved our stay at this stunning home! The hot tub and sauna and the views were major highlights for our 10 year anniversary trip! Great for a weekend away!
Top guest favorite
Home in Germantown
4.95 out of 5 average rating, 426 reviews

Rustic Swedish Barn/Featured in Airbnb Magazine

GabriellaRating, 5 stars1 week ago
We enjoyed the perfect escape from the city in this magical barn with gorgeous antiques and pristine views. Definitely will be back for future celebrations!
Top guest favorite
Home in Rhinebeck
5 out of 5 average rating, 212 reviews

Eagle Rock House

BeatrizRating, 5 stars3 days ago
Edina and Glen's house was beautiful, spacious, and pristine. It was the perfect setting for a "girls weekend". The grounds were stunning, and made for a great setting. Very close to town, shopping, and wonderful restaurants. We really appreciated that our hosts were very proactive in reaching out and making all instructions clear. They were communicative and flexible. Thank you for having us in your beautiful home! Very memorable weekend.

Family friendly vacation rentals in The Berkshires

Guest favorite
Apartment in Plainfield
4.97 out of 5 average rating, 271 reviews

Sunny, light filled loft in 1873 Colonial

DouglasRating, 5 stars1 week ago
Peter and the apartment were great! Peter was super responsive, friendly, and had nice touches like homemade granola with milk and coffee provided. After my original AirBNB fell through at check-in at 6pm, I was relieved (and saved) by Peter’s responsiveness.
Top guest favorite
Guesthouse in Stephentown
5 out of 5 average rating, 416 reviews

Dog Friendly Studio

LilyRating, 5 stars1 week ago
We absolutely loved Maple Hill Farms. It's a wonderful place and a perfect choice for a trip to the Berkshires if you're an animal lover. The best part of our weekend was bonding with Philip's sweet and friendly donkeys! The studio is well laid out with everything you need, the farm is beautiful and peaceful (except for the roosters, haha!), and the location is great for visiting local sights like Mass MoCA and The Mount. We hope to be back!
Guest favorite
Guesthouse in Lenox
4.93 out of 5 average rating, 105 reviews

The East Street Cabin

PeterRating, 5 stars7 months ago
We were in Lenox to attend a reunion for the Lenox School for Boys ( Grad “66” ). The cabin was perfect for our needs especially because we could have our dog with us. Most of our time was spent with activities scheduled for the reunion so we didn’t really get to enjoy the peaceful atmosphere surrounding the cabin. There will be another reunion in 2026 so we will be looking forward to another stay at the Luv Shack. Thanks for sharing your abode. Pete & Becky Davis Mechanicsburg PA
Top guest favorite
Apartment in Plainfield
4.95 out of 5 average rating, 270 reviews

Sunny carriage house apartment

MicheleRating, 5 stars1 month ago
Beautiful home, many thoughtful touches to make traveling easy and comfortable! Thank you!
Top guest favorite
Cottage in Shaftsbury
4.98 out of 5 average rating, 692 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

LaurenRating, 5 stars2 weeks ago
My partner and I had a wonderful and peaceful stay! The schoolhouse is very cozy, with beautiful views, and the baby sheep were adorable and so fun to watch. Caroline was very responsive and kind! I’d recommend their place to anyone in a heartbeat.
Guest favorite
Cottage in Ashfield
4.96 out of 5 average rating, 346 reviews

hope house

JohanRating, 5 stars2 weeks ago
"So peaceful and quiet that you can hear the grass grow." The restaurant around the corner is actually a town-center where the best of small-town America is exemplified. Lots of social contacts, a local newspaper describing the wonderful Little America that still exists, artisan cakes and breads, health conscious, and excellent coffee to boot. We found the other local restaurants to be gems as well. When the graduation schedule of our son hit our calendar, we were faced with the fact that the 16miles from Amherst take a 40 minutes' drive. So close, so far away. Stay in Ashfield, become one with the locals, they'll embrace you.
Guest favorite
Tiny home in Jamaica
4.94 out of 5 average rating, 1,269 reviews

Apple Blossom Cottage: A Tiny House

LauraRating, 5 stars3 days ago
I had an amazing time at your location. I was able to use it as a home base for all the different hiking trails in the area. Your property is really quiet and peaceful. I loved being able to enjoy nature and breathe in some fresh air.
Top guest favorite
Cabin in Red Hook
4.96 out of 5 average rating, 352 reviews

Modern Upstate Cabin, near Rhinebeck NY

EllieRating, 5 stars2 weeks ago
We recently stayed at Tina's and had a great time. The location is secluded, incredibly peaceful and quiet — all you can hear are the birds in the morning. The home itself is clean and looks just like the photos. We also loved that we could bring our dog along with us. We live in the city so our pup doesn't get to touch much grass, and he had a blast running through the fenced-in yard. Although we originally booked because the house has a pool and we were hoping for good weather, it rained almost the entire time we were there... Nonetheless, it felt like the coziest home for a rainy weekend, and we really enjoyed our stay. We loved sitting inside by the fire to watch a movie, cooking in the kitchen and building a fire outside when the rain stopped. The location was also great for driving into Rhinebeck, Red Hook, Hudson and surrounding breweries and wineries.

Destinations to explore