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Vacation rentals in Cheshire

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Popular amenities for Cheshire vacation rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Other great vacation rentals in Cheshire

An outdoor deck is presented with a large wooden table surrounded by chairs. Colorful cushions add comfort, and potted flowers brighten the space. Soft string lights hang above, illuminating a hammock and lounge chairs nearby, all set against a backdrop of lush greenery.
Guest suite in Hancock
4.81 out of 5 average rating, 180 reviews

Cozy apartment near Jiminy Peak

KatieRating, 5 stars3 months ago
We loved staying with Naren! She was very accommodating and has a beautiful home:) Highly recommend and would love to return!
Top guest favorite
A wooden porch features two Adirondack chairs and a small footrest, all in a rich brown hue. Natural light filters through the nearby windows, illuminating the wooden flooring and the inviting setting. A storage box is positioned beside the chairs.
Vacation home in Williamstown
4.98 out of 5 average rating, 96 reviews

ALL welcome: Lovely 1 BR studio, Berkshires beauty

SamRating, 5 stars3 months ago
The hosts were very helpful in general, and responded immediately to take care of a minor issue we mentioned. The studio in the barn is clean, comfortable, and well set up. It's a great spot for 1-2 people. The only minor complaint (which is out of the host's control) is that my wife and I use Verizon, and the studio was a dead zone for cell service for us [when we needed to make a call, we 'solved' this problem by walking down the driveway towards the road, where we got signal]. Wi-Fi in the studio worked great for computer use and streaming, so that is not an issue, just Verizon cell service. We had a great stay overall!
Guest favorite
An open-concept living space features a wooden bar with high stools, set against a backdrop of a stone fireplace. Natural light fills the area, highlighting the exposed wooden beams in the ceiling and creating a warm, cozy environment.
Cabin in Windsor
4.9 out of 5 average rating, 10 reviews

Stone cabin in the Berkshires

JenniferRating, 5 stars1 week ago
This stone cabin in the woods is a great place to decompress and read a book, or write a book. The space is comfortable and cozy, with beautiful indoor and outdoor areas. Irene is a great host—she guided us through finding the place and answered questions promptly, but mostly left us alone to enjoy the beautiful surroundings. The cabin is quiet and in the woods, but within easy striking distance is excellent restaurants—shout out to the chocolate chip pancakes at M&Js in Adams.
Farm stay in Adams
5 out of 5 average rating, 3 reviews

Berkshires/Pet Friendly farm stay w/mountain views

IsabelleRating, 5 stars2 weeks ago
My three friends and I had a wonderful weekend stay at this airbnb. From the start Jessica, the host, was in touch and responsive to any questions I had. The RV itself was perfect, exactly what my group was looking for and was as advertised. A lovely guest-ready camper, a fire pit, great views and outdoor spaces, accessibility, chairs with an umbrella, a picnic table, a hammock that could be set up, easy storage for all of these things, and friendliness from the host next door. We were able to comfortably sleep 4 people for 3 nights. My group have discussed returning when we can because we had such a positive experience. We hope that others will get the opportunity to make memories in Adams, MA as we did during our stay this summer. All I have to say are good things about this location and the people who run it. I would absolutely recommend it :)
Top guest favorite
A set of double doors features rustic wood with an X-pattern design, providing an inviting entryway. The doors are fitted with black handles and surrounded by a white trim, complementing the warm wooden flooring visible in the foreground.
Apartment in Adams
4.99 out of 5 average rating, 73 reviews

Charming/Rustic Apartment with downtown views

JeffRating, 5 stars1 week ago
Adams is a beautiful little town, and Michele's place is right in the middle of it. Everything was as described and was VERY clean and comfortable. I was there for the MoCA in North Adams, access to Mount Greylock, and the rail trail and this was the perfect location. The weather thwarted many of my plans, but this place was plenty cozy enough to just hang out in and wait for breaks in the rain! I would definitely stay here again! Michele is a wonderful host, friendly and responsive.
Guest favorite
A modern kitchen features gray cabinetry and stainless-steel appliances, including a microwave and stove. A sleek white refrigerator stands against the wall. Natural light floods the space through a window, highlighting the wooden flooring and clean, spacious countertops.
Apartment in Pittsfield
5 out of 5 average rating, 37 reviews

Comfy Quaint Tavern

MarkRating, 5 stars3 months ago
Amy is a fantastic host and has thought of everything you need while staying here. It’s convenient to everything in town and feels like home.
The Victorian farmhouse features intricate architectural details on the porch, including decorative trim. Greenery surrounds the entrance, with a large garden and trees visible in the background. A pathway leads from the porch to the adjacent yard, enhancing the home's inviting appearance.
Home in Adams
4.93 out of 5 average rating, 247 reviews

1890 House

Wen OngRating, 5 stars3 weeks ago
kate’s home was a cozy and peaceful retreat. she was super responsive, even with our late check-in, and the house had everything we needed to unwind — especially the fireplace, which we used almost every day. the kitchen was well-equipped, and we loved exploring the local food spots and hiking trails nearby. overall, a lovely stay — we’d definitely come back!
Guest favorite
The kitchen features wooden cabinetry and granite countertops, complemented by stainless steel appliances. A large island with a stovetop provides additional workspace, while a refrigerator and coffee maker are visible. Natural light streams in through a window, enhancing the airy atmosphere.
Home in Adams
4.91 out of 5 average rating, 33 reviews

Golf House by Mt Greylock - Walkable Adventures!

RodahRating, 5 stars1 week ago
Just felt like home, huge space Micheal’s communication was just on point we had aloot of fun with my family everything was on point from the rooms to the kitchen just in point.
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