Vacation rentals in The Berkshires

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Popular amenities for The Berkshires vacation rentals

House rentals in The Berkshires

Top guest favorite
Home in Andes
4.99 out of 5 average rating, 235 reviews

Delaware House Inn - Farmhouse

ConorRating, 5 stars3 weeks ago
We’ve stayed at Skip’s listings a few times, and it’s been wonderful each stay. Skip is helpful and quick to answer any questions. Andes is the most beautiful town. Highly recommend!
Guest favorite
Home in Athens
4.84 out of 5 average rating, 170 reviews

A Victorian "Lady"

RonaldRating, 5 stars5 months ago
Well kept clean old house and furnishings. Terrific unobstructed view of the Hudson from two of the bedrooms and living room facing East. I loved sitting by the bay window in the master bedroom with the sun shining in watching barges on the river and with views of the town of Hudson on the far side of the river. The owners stuff was in the closets and refrigerator and freezer full of her food but that did not bother me. I appreciate having condiments, salt, sugar and pepper available. There is a washer/dryer but no dishwasher and only one bathroom. Also no shades on the East facing window in the master bedroom so light streamed in at sunrise.
Guest favorite
Home in Albany
4.81 out of 5 average rating, 52 reviews

Airy 5Br-2Ba,Kids Rm, 6TVs,Pvt Fence-yard&Parking!

BjRating, 5 stars3 months ago
Rashawn's place was great! Near downtown Albany, and plenty of sleeping space. Great for any size groups.
Top guest favorite
Home in Cheshire
5 out of 5 average rating, 133 reviews

Pool House

EllenRating, 5 stars2 weeks ago
Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.
Guest favorite
Home in Fleischmanns
4.96 out of 5 average rating, 45 reviews

Open Plan Living; Mountain Views

DavidRating, 5 stars1 month ago
Mary was a very nice, responsive and welcoming host . I would definitely stay at Halcott House again
Superhost
Home in Hurley
4.88 out of 5 average rating, 156 reviews

Charming private cape house in Woodstock

AngelaRating, 5 stars4 months ago
Lola's place was clean, quiet, comfy and well situated for our needs. The house is well equipped, including butter, milk and eggs in the refrigerator (nice touch). Lola is very responsive, answering any question we had in a timely manner. We would definitely recommend and stay here again.
Guest favorite
Home in New London
4.94 out of 5 average rating, 134 reviews

House in NL near CGA, Sub Base, Mohegan Casino

MeaganRating, 5 stars5 months ago
Our family opted for a trip to New London to reconnect with our family for Thanksgiving. We were able to utilize the beautiful dining room for our dinner . We loved staying at Rosa’s place and were very comfortable . Just a note - there is only one bathroom and it is on the second floor ( as are all the bedrooms) We made this work but can be difficult with a larger family . It would definitely not deter me from booking again! This place was beautiful. The surrounding area and ease of access was comforting ! Would definitely stay here again .
Top guest favorite
Home in Old Saybrook
4.97 out of 5 average rating, 121 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

SueRating, 5 stars1 week ago
Laurie s place is very nice, spacious and clean. Plenty of space to eat, hang out and 2 bath. The fenced in yard is great for dogs or kids. We weren't in full summer season so we're not taking advantage of the beach and water options but they offer alot. Allowed for an early check in which was great as we were in town for a memorial service.

Cabin rentals in The Berkshires

Guest favorite
Cabin in Arkville
4.98 out of 5 average rating, 123 reviews

Little Log Cabin with Hot Tub

KateRating, 5 stars2 months ago
The Little Log Cabin was the perfect long weekend getaway. It was so comfortable and cozy. I would love to return the next time I’m in the Catskills. Thank you Becca and Jesse for sharing such a wonderful home!
Guest favorite
Cabin in Margaretville
4.94 out of 5 average rating, 158 reviews

Catskills log cabin in the sky with mountain views

StephanieRating, 5 stars3 weeks ago
Amazing location to disconnect and recharge.
Top guest favorite
Cabin in Palenville
5 out of 5 average rating, 265 reviews

Big Medicine Ranch-Rustic Sunrise Cabin-Catskills

NikkiRating, 5 stars2 weeks ago
So beautiful! Had a great time just relaxing in the cabin. Very clean and comfortable. Brian and Stephanie were so kind and quick to respond. Will absolutely book again, especially in the summer!
Superhost
Cabin in Avon
4.96 out of 5 average rating, 102 reviews

Charming Cabin on Farmington River

SakaraRating, 5 stars6 months ago
Had an absolutely lovely stay at Billy's cabin! We only stayed one night but it was everything we could have hoped for. Being able to take the canoe out on the river was amazing. Even with the road on the other side of the river it was extremely peaceful. We ate out for every meal since town was so close and easy to get to. All we brought with us was some firewood, water, and an air mattress/blankets/pillows. Would definitely stay here again!!
Guest favorite
Cabin in Windham
4.96 out of 5 average rating, 117 reviews

The Creekside Cabin - 5 mins to Windham Mt!

ElsaRating, 5 stars2 weeks ago
We loved our stay at the Creekside Cabin! The space is cozy, recently renovated, and the kitchen is well equipped with everything we needed. The living room gets beautiful natural light and offers a lovely view of the creek. My toddler especially loved being so close to the water and the forest—it made for such a peaceful and fun experience. The location is perfect for families, with toddler-friendly hikes and even pony rides just a short drive away. Jill was a fantastic host. We would absolutely come back!
Top guest favorite
Cabin in Jefferson
5 out of 5 average rating, 479 reviews

"Far from the Madding Crowd" Cozy Cabin Retreat

TaschaRating, 5 stars1 week ago
I believe one of the best compliments to any AirBnB host is returning to their property: this was our fourth visit to the Clack Cabin, and surely not our last! We love the Clack Cabin for its coziness, comfort, and location. It's a small space, but has absolutely everything one needs. It's incredibly peaceful and relaxing, with the stream providing such a soothing soundtrack. The Clapper Hollow State Park a few steps away from the cabin has many easy and quiet paths to explore (we had the forest entirely to ourselves on Easter Sunday!). Clara is a wonderful host, very welcoming and helpful with local tips and knowledge. We already look forward to our next visit!
Top guest favorite
Cabin in Smallwood
4.97 out of 5 average rating, 246 reviews

Beautiful & Secluded Streamside Catskills Cabin

RichardRating, 5 stars5 days ago
This was our second vacation at this cabin and it was even more cozy for being familiar to us. We had a wonderful 8 days in nature and had a very hard time leaving. Smallwood forever!!!!
Top guest favorite
Cabin in Mount Tremper
4.92 out of 5 average rating, 256 reviews

Charming Cabin on rushing stream

CoriRating, 5 stars2 months ago
Very comfortable and felt great to be inside this special little cabin. We brought our dogs and they were well accommodated here. The immediate road the house is on isn’t the best for walks but there’s lots of beautiful trails just a short drive a way. Although we were there during a very icy winter, I think the river behind the house would be fun to enjoy other seasons. Also great restaurants super close to the house.

Pet-friendly vacation rentals in The Berkshires

Top guest favorite
Guesthouse in Southbury
4.93 out of 5 average rating, 319 reviews

Charming Guest Cottage with Modern Amenities

CarolineRating, 5 stars3 months ago
John’s place was the perfect respite for our multi-day stay! The clean and cozy space is perfectly situated close to trails and parks for our Australian shepherd, but only a short drive to all the shopping you’d need (e. g. ShopRite for groceries and necessities). We thoroughly enjoyed our stay and know you will too!
Guest favorite
Home in Saugerties
4.87 out of 5 average rating, 126 reviews

Le Petit Cottage - French Country in Saugerties

SwetaRating, 5 stars2 months ago
This cottage was even better than the pictures! Such great details and charm - plenty of space and cozy at the same time. Wood-burning stove perfect for the winter. Fully stocked kitchen, comfortable bedrooms and spacious bathrooms. Location was convenient and very close to Saugerties. Super responsive and helpful host as well. Would highly recommend!
Guest favorite
Apartment in Corinth
4.8 out of 5 average rating, 131 reviews

Adirondack Penthouse, Sleeps 10. Steps from Beach.

OtonielRating, 5 stars3 months ago
This was our second time staying at Craig and Deb's place ✨ it was wonderful as always! place is clean, cozy and warm. They're very attentive, and the area feels safe, convenient supermarket nearby. A must stay if going skiing at West Mountain.
Guest favorite
Cabin in Woodstock
4.97 out of 5 average rating, 148 reviews

Pet Friendly Cabin Doh-Ray up at 1450 ft

JosephRating, 5 stars2 months ago
Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.
Superhost
Cottage in Kerhonkson
4.9 out of 5 average rating, 183 reviews

*spring-ready* Pet-friendly private cabin!

KyleRating, 5 stars3 weeks ago
Darla’s cottage was such a sweet spot for a weekend getaway. Super cozy, clean, and peaceful—exactly what we were looking for. It felt tucked away in the woods but still really easy to get to, and just a few minutes down the road from Rough Cut Brewing, which was a big plus. We loved being able to grab some beers, then come back and relax inside. Darla was a great host—friendly, but gave us plenty of space. Would totally stay again next time we’re in the area!
Top guest favorite
Bungalow in Hurleyville
5 out of 5 average rating, 134 reviews

Romantic Agrihood Getaway Bungalow-Fireplace/WiFi

ChrisRating, 5 stars4 days ago
We had a brief stay, but what a cute place. Bravo! Was perfect place for us!
Top guest favorite
Cabin in New Paltz
4.97 out of 5 average rating, 151 reviews

New Paltz dog friendly retreat w/salt water POOL

PaulRating, 5 stars6 months ago
Excellent stay for a small group - we only stayed for a weekend, but would be a perfect spot for a weeklong trip as well.
Superhost
Home in West Kill
4.93 out of 5 average rating, 121 reviews

Catskill Mountain Cabin Waterfall Retreat

TatyanaRating, 5 stars3 months ago
I enjoyed my stay at Gavin and Alison's house in the Catskills. It was a great place to spend a snowy winter weekend in January with my son and two grandchildren. The house is a short drive from various skiing and winter-sports resorts. We were satisfied with the kitchen and other amenities, played board games, and generally had a relaxing time. The hosts were very responsive when we had questions.

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