Photo by Ed Gaffny

Holiday Rentals in Cheshire

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Holiday Rentals in Cheshire

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (84)
"This old barn was renovated into a great place to stay. Jane and Ian paid careful attention to details, light, colors, materials. Very comfortable and relaxing. The setting is gorgeous, and the sheep are fun. (FYI: It may be helpful to understand the layout and bathrooms: the new bathroom is at the far end of the smaller bedroom. This works great for a couple to have their own bathroom. The other bathroom is within the larger bedroom with the bunk bed, but in an area close to the door,...
19th c. Barn in the Berkshires

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1763)
"In door pool was very nice. Room was clean and had all the basics. "
The price is €130
includes taxes & fees
23 Feb - 24 Feb
Vacation Village in the Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (925)
"Staff was exceptionally helpful and friendly."
The price is €198
includes taxes & fees
23 Feb - 24 Feb
Jiminy Peak Mountain Resort

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is €222
includes taxes & fees
20 Feb - 21 Feb
Berkshire Village Carriage House - Super Private!!

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (139)
"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (118)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Cabin in the woods

10.0 out of 10, Exceptional, (9)
"This place was awesome... I was 15 minutes away working late... and I was too tired to drive home... I actually scheduled the wrong night and realized it after I got confirmation. But I messaged the renters and they just happened to have a cabin vacancy... they gave me the directions.. the key code and we worked everything out afterwards. The set-up is genius... the common area building has all the plumbing in it. Bathroom and showers with an open very well built living room with a kitchen. My...
The price is €166
includes taxes & fees
18 Feb - 19 Feb
Cabin in the woods

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

9.8 out of 10, Exceptional, (41)
"This property is stunning. It fit our group of 14 perfectly. There are so many unique details and beautiful furniture. The kitchen was well-stocked for pots/pans/utensils/cleaning supplies which I always appreciate - makes group meals so much easier to manage. Quiet area, would be great all year round depending on what activities you like. Hot tub was a major highlight!"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Amore Estate - beautiful room with many places to explore and relax in.

9.4 out of 10, Exceptional, (21)
"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"
Amore Estate - beautiful room with many places to explore and relax in.

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (9)
"Annual mother/son ski and food fest!Lots of fun with family and friends. Plenty of space for everyone.. Kitchen wascwell"
The price is €1,070
includes taxes & fees
25 Feb - 26 Feb
Hancock Village Inn at Jiminy Peak

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (55)
"Perfect lake front home to get away for a quick weekend trip with the family over the holidays!! Location, location location, close proximity to downtown Pittsfield, 15 from Jiminy peak & Bousquet Mt. Andrey was extremely helpful throughout the process with suggestions for food and activities for the kids. The house was a perfect fit for our family and friends. Everyone enjoyed their time there and would definitely book again"
Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (10)
"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "
Wellspring by AvantStay | Indoor Pool + Views

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (65)
"Beautiful home perfect for our multi-generational family. We loved the separate spaces and easy walk to the town center. We can’t wait to come back!"
Enjoy comfortable elegance in this secluded grand home located in town

Peace and quiet on the lake

9.6 out of 10, Exceptional, (208)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake

Mountainside Condo Ski In Ski Out

9.0 out of 10, Wonderful, (23)
"Great great in ski out stay; neat & clean. "
The price is €184
includes taxes & fees
24 Feb - 25 Feb
Mountainside Condo Ski In Ski Out
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Cheshire you may be interested in

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.6 out of 10, Excellent, (1002)
"Staff were extremely nice and accommodating."
The price is €133
includes taxes & fees
23 Feb - 24 Feb
Hotel Downstreet, Ascend Hotel Collection

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1763)
"In door pool was very nice. Room was clean and had all the basics. "
The price is €130
includes taxes & fees
23 Feb - 24 Feb
Vacation Village in the Berkshires

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (499)
"Excellent"
The price is €103
includes taxes & fees
2 Mar - 3 Mar
Life House Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find a holiday rental in Cheshire?

Yes, there are holiday rentals close to the most popular sights in Cheshire, or you can select a more secluded option if you're looking for a relaxing stay. Cheshire is known for its ski areas and restaurants. Make sure you have time to check out the lake views and shopping during your trip.

What are some of the best holiday rentals that Cheshire has to offer?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Cheshire is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

What can I see and do in Cheshire?

While exploring the area, visit family-friendly sights like Berkshire Museum, or get outside and enjoy nature at Mount Greylock State Reservation. In the wider area, you’ll find St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center.

What are holiday rentals like in Cheshire?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cheshire. Holiday rentals feature extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family gatherings.