
Vacation rentals in The Berkshires
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Top-rated vacation rentals in The Berkshires
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Popular amenities for The Berkshires vacation rentals
House rentals in The Berkshires

A Victorian "Lady"
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.

Airy 5Br-2Ba,Kids Rm, 6TVs,Pvt Fence-yard&Parking!
Rashawn's place was great! Near downtown Albany, and plenty of sleeping space. Great for any size groups.

Pool House
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.

Open Plan Living; Mountain Views
Mary was a very nice, responsive and welcoming host . I would definitely stay at Halcott House again

Beautiful, cozy house for rent
Lovey home and very convenient location in Willamstown. Would highly recommend.

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

3 bdrm house great neighborhood
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.

Peaceful Blossoms Victorian Home
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

Charming Guest Cottage with Modern Amenities
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!

Le Petit Cottage - French Country in Saugerties
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!

Adirondack Penthouse, Sleeps 10. Steps from Beach.
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.

Pet Friendly Cabin Doh-Ray up at 1450 ft
Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.

*spring-ready* Pet-friendly private cabin!
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!

Romantic Agrihood Getaway Bungalow-Fireplace/WiFi
We had a brief stay, but what a cute place. Bravo! Was perfect place for us!

"Far from the Madding Crowd" Cozy Cabin Retreat
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!

New Paltz dog friendly retreat w/salt water POOL
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

Bright Farm House- Tranquil setting
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!

Waterfront 3BR Home in Hudson Valley, Catskills
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!

Winston's Place - Woodland Cozy Catskills Cabin
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!

Peaceful Cabins by the river, excellent wifi!
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!

Whole place,staycation,3 bedrooms, spacious area
Exactly what we needed to visit our family in Granby!

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

Sweeping mountain views in Woodstock, NY
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.

Family weekend getaway
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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