Vacation rentals in The Berkshires

Book unique homes, vacation rentals, and more on Airbnb

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Popular amenities for The Berkshires vacation rentals

House rentals in The Berkshires

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
Top guest favorite
Home in Williamstown
5 out of 5 average rating, 13 reviews

Beautiful, cozy house for rent

SteveRating, 5 stars5 months ago
Lovey home and very convenient location in Willamstown. Would highly recommend.
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.
Guest favorite
Home in Enfield
4.91 out of 5 average rating, 11 reviews

3 bdrm house great neighborhood

J DavidRating, 5 stars11 months ago
Wonderful place for our family to spend the weekend while we attended our daughter's graduation a half hour away in MA. Clean, comfortable, spacious and charming in a quiet neighborhood. Auria provided clear instructions, check in was a breeze, and she was extremely proactive and helpful. She responded immediately to questions and was always cheerful and polite. One of the best Airbnb experiences we have had so far. I can not recommend this highly enough.
Guest favorite
Home in Greenfield
4.9 out of 5 average rating, 191 reviews

Peaceful Blossoms Victorian Home

AmandaRating, 5 stars4 months ago
We didn’t spend much time in the home as we were in town to visit family for the holidays but the home was just as pictured and Carolyn and Evan were very friendly. The home was comfortable and clean and had everything we needed for our stay. Carolyn was great about letting us know when someone was over to check on the furnace or to remind us to take care as there was freezing rain and the walkways were slick. But she and Evan were also over early in the mornings laying down salt to make the walkways less icy. I would highly recommend this place to anyone who wants a clean comfortable home with friendly, responsive hosts. I am from the area and the location is very central to other small towns as well as walkable to coffee shops and the downtown area. She even put up a Christmas tree for the holidays!

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 stars3 days ago
We had a brief stay, but what a cute place. Bravo! Was perfect place for us!
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 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.

Family friendly vacation rentals in The Berkshires

Top guest favorite
Farm stay in Goshen
4.87 out of 5 average rating, 348 reviews

Bright Farm House- Tranquil setting

ScottRating, 5 starstoday
We had a wonderful family stay at Jacquelyn's farmhouse! It is a large, comfortable and nicely furnished house and while it is an old house, it is in great condition and clean. It sits on a beautiful piece of property with a stream running through and farm animals that are kids had a blast feeding! The house and kitchen was well stocked and had everything we needed. Highly recommended for a stay in the Goshen area, and it is conveniently located right near Legoland!
Top guest favorite
Home in Lake Katrine
4.95 out of 5 average rating, 111 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

NathanRating, 5 stars4 months ago
This place was a breath of fresh air. I've noticed a trend on AirBNB of rentals that are obviously flipped investment properties with no character and no evidence of life: this place is the opposite! Charming, comfortable, with hosts who actually know the area and live in the area. This is a great family option when visiting the surrounding Hudson Valley towns. I hope I can get back here soon!
Top guest favorite
Cabin in Boiceville
4.98 out of 5 average rating, 501 reviews

Winston's Place - Woodland Cozy Catskills Cabin

NatalieRating, 5 stars3 weeks ago
We had such a wonderful stay here! Such a cozy and lovely cabin in a beautiful location. Nickie was also super responsive and helpful. We will definitely be back!
Guest favorite
Cabin in Accord
4.94 out of 5 average rating, 112 reviews

Peaceful Cabins by the river, excellent wifi!

Steve & DoreenRating, 5 stars4 months ago
What a magnificent spot! If nothing else, the creek next to the house was worth the price of admission. But the whole experience was fantastic. We filled the place up, and had a dozen more family members come for Thanksgiving dinner. It was cozy and the extra kitchen in the cabin was a godsend. We loved being there, and everything about our stay was perfect. Thank you!
Guest favorite
Guest suite in Granby
4.91 out of 5 average rating, 144 reviews

Whole place,staycation,3 bedrooms, spacious area

VictorRating, 5 stars4 months ago
Exactly what we needed to visit our family in Granby!
Top guest favorite
Chalet in Dover
4.97 out of 5 average rating, 113 reviews

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB

CaterinaRating, 5 stars1 month ago
Great location! This was a two family trip up to Mt Snow. We had a wide range of ages and 2 dogs. The house had plenty of toys and things for the kids to do - their favorite was the scavenger hunt! The kitchen is one of the best stocked kitchens compared to other Airbnbs we have used. The beds were comfortable - plenty of extra pillows and blankets. The couch and chairs in the living area were also very comfortable. The hot tub was very nice and enjoyable after everyone went skiing.
Top guest favorite
Home in Woodstock
4.98 out of 5 average rating, 219 reviews

Sweeping mountain views in Woodstock, NY

DanielRating, 5 stars1 month ago
We had a lovely stay! The place was very relaxing, peaceful, and surrounded by nature, yet still close to Woodstock. One of the highlights was seeing a family of deer right outside our window — such a special moment. The hosts were also incredibly accommodating, providing a highchair and pack ’n play for our infant, which made our stay so much easier. We truly appreciated their thoughtfulness and hospitality. Highly recommend to anyone looking for a quiet getaway close to town.
Guest favorite
Home in Beacon
4.95 out of 5 average rating, 131 reviews

Family weekend getaway

ShayRating, 5 stars2 days ago
We had a great one night stay during our weekend of hiking in the Beacon area. The place is easy to find and is in a very quiet neighborhood. The host was super nice and flexible. The kitchen is very well equipped. The following part is not a problem and did not change the five star review - just a service announcement for the next guest:-) Some Airbnbs have spices and oil for cooking and some don't. It's very random. This one has almost nothing so bring your own or get what you need at the nearby store. In terms of equipment, I haven't seen many kitchens that had such a variety. we'll definitely be back

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