Vacation rentals in The Berkshires

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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 stars4 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, 46 reviews

Open Plan Living; Mountain Views

JoeRating, 5 stars1 month ago
This property was absolutely amazing. I can’t wait to come back!!!!
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.
Top guest favorite
Home in Canajoharie
4.92 out of 5 average rating, 161 reviews

2 homes on large private mountain views getaway

PeterRating, 5 stars1 week ago
Absolutely beautiful home with incredible views. Very fair price and very peaceful. Thanks for the great stay, Amos!!
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 stars2 weeks 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.
Top guest favorite
Home in Greenfield
4.9 out of 5 average rating, 192 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!

Family friendly vacation rentals in The Berkshires

Top guest favorite
Farm stay in Goshen
4.87 out of 5 average rating, 350 reviews

Bright Farm House- Tranquil setting

KimRating, 5 stars6 days ago
We had a nice time. It was fun to feed the animals and visit them everyday. We bought apples and carrots from the grocery store to feed them. It is very close to Legoland. It is a good birding spot and the stream nearby is nice to walk to. There were lots of flying bugs outside during our stay. Which is expected during spring near farm animals and by a stream. Just be prepared for that. Overall, we had a comfortable stay and this home was a nice getaway.
Top guest favorite
Cabin in Boiceville
4.98 out of 5 average rating, 504 reviews

Winston's Place - Woodland Cozy Catskills Cabin

WillRating, 5 stars1 week ago
We had an amazing stay! Very cozy home in a beautiful area of Hudson Valley. Nickie was very helpful and quick to respond with answers to any questions we had. 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 stars5 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
Townhouse in Saugerties
4.93 out of 5 average rating, 309 reviews

15 min to Woodstock/Saugerties/Hunter (2 bedroom)

HaigRating, 5 stars2 months ago
Good location, nice cozy place. Easy to follow instructions from the host, who was also quickly responsive.
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 stars2 months 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
Cabin in Jefferson
5 out of 5 average rating, 479 reviews

"Far from the Madding Crowd" Cozy Cabin Retreat

TaschaRating, 5 stars2 weeks 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
Home in Woodstock
4.98 out of 5 average rating, 220 reviews

Sweeping mountain views in Woodstock, NY

AndrewRating, 5 stars6 days ago
We had an absolutely lovely stay at John and Kelly's mountain retreat. Everything we could have wanted or needed -- coffee, linens, towels, etc -- was there for us. It was so tastefully appointed and just a joy to spend time there. And the views! Wow! We hope to come back here soon. Thanks for being exceptional hosts. Five stars all around!

Dog 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 stars4 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!
Superhost
Home in Woodstock
4.84 out of 5 average rating, 110 reviews

2 BR , Fireplace & Hot Tub @ heart of Woodstock

AndrewRating, 5 stars2 months ago
We had a wonderful time at Mirav’s place in Woodstock. Made great use of the hot tub and the fireplace. We absolutely plan on returning soon!
Top guest favorite
Home in Philipstown
4.93 out of 5 average rating, 130 reviews

Cozy 3 bedroom house on quiet private road

FrancesRating, 5 stars6 days ago
Our stay at Melanie’s place was wonderful! Honestly such a great stay with some really thoughtful touches. Melanie was communicative and responsive. We had brought our two dogs and Melanie made sure to put out a dog bowl and dog bed for them along with fresh flowers on the table! The place was also extremely clean, had comfy beds, was spacious and has a really nice back space looking onto a small creek and beautiful woods. The photos honestly don’t do it justice! The location was perfect for us as we had activities in Bear Mountain. Thanks so much, Melanie! Would love to stay again if we ever need to be in the area again.
Top guest favorite
Chalet in Dover
4.97 out of 5 average rating, 110 reviews

Mountain Chalet: Private Brook - Hot Tub - Firepit

EricRating, 5 stars1 month ago
Family had a great stay at Danielle and Ben’s the house was very clean and kid friendly and we really enjoyed having the view of the creek from decking area. Very close to Mt Snow and surrounding area restaurants and attractions. Would stay again.
Superhost
Cottage in Carmel Hamlet
4.81 out of 5 average rating, 156 reviews

Cozy Dogfriendly Cabin & Backyard on Scenic Lake.

AlexRating, 5 stars1 month ago
cannot recommend this cottage enough. aside from the fact that it's a hop, Skip and jump away from a beautiful swimmable lake, the property itself is gorgeous and perfect for dog people. we spent a night in the backyard with the fire, and another night inside stoking the indoor fireplace while we cook dinner and play board games. everything is as the host described, wylda is extremely proactive in her communication and pretty much read our minds in terms of what we would need and or want. she also decorated in the most beautiful way. it feels like a home, not some weird cookie cutter situation, it's clean and interesting and fun. I can't believe it's only an hour and a half away from Brooklyn.
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.
Guest favorite
Cottage in Bethlehem
4.98 out of 5 average rating, 103 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

LyndaRating, 5 stars6 days ago
Kelsey’s cottage was exactly as described. It was so beautifully decorated & had everything that we would need. We had a wonderfully relaxing weekend & hope to do it again soon.
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.

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