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Cheshire Holiday Rentals

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Holiday Rentals in Cheshire

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (983)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is AU$241
includes taxes & fees
26 Oct - 27 Oct
Jiminy Peak Mountain Resort
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2096)
"Great place!"
United States
Nicole
The price is AU$175
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is AU$374
includes taxes & fees
29 Oct - 30 Oct
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Park Street Penthouse Apartment
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is AU$305
includes taxes & fees
27 Oct - 28 Oct
Park Street Penthouse Apartment
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
10.0 out of 10, Exceptional, (8)
"Great location. Howie is very communicative. Wish we could have stayed longer. "
United States
Una D.
The price is AU$376
includes taxes & fees
28 Oct - 29 Oct
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Florida Mountain Log Cabin!
2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is AU$632
includes taxes & fees
26 Oct - 27 Oct
Florida Mountain Log Cabin!
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
10.0 out of 10, Exceptional, (3)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
10.0 out of 10, Exceptional, (4)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is AU$374
includes taxes & fees
29 Oct - 30 Oct
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
9.4 out of 10, Exceptional, (16)
"We absolutely enjoyed this pleasant apartment. Its within the walking distance from the ski lifts which was perfect for all of us including 5 year old kid. "
United States
Janja
The price is AU$374
includes taxes & fees
29 Oct - 30 Oct
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, (14)
"Clean and quiet, nicely decorated! "
United States
Robert
The price is AU$487
includes taxes & fees
24 Oct - 25 Oct
UNIQUE - 1BR Country Condo @ Jiminy Peak
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (33)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
9.6 out of 10, Exceptional, (30)
"We really enjoyed our stay it was a very nice place for a family."
United States
Shmaya G.
The price is AU$504
includes taxes & fees
27 Oct - 28 Oct
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
8.0 out of 10, Very good, (8)
"Cozy little condo, good for a group of four or five. We stayed there with my two kids 8 &10 and wife. It’s a nice place overall we had a great time. It is a short drive to the slopes, which is fine as long as you have a car but you still need to park at the inn"
United States
Sam R.
The price is AU$525
includes taxes & fees
12 Nov - 13 Nov
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
2-Bdr Apt In Town, By the Water
9.4 out of 10, Exceptional, (9)
"Lovely property, in good shape. Close to many Williamstown attractions."
United States
Scott M.
The price is AU$420
includes taxes & fees
3 Nov - 4 Nov
2-Bdr Apt In Town, By the Water
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
10.0 out of 10, Exceptional, (2)
"as advertised."
United States
Joshua G.
The price is AU$977
includes taxes & fees
3 Nov - 4 Nov
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Bear Creek Cabin
10.0 out of 10, Exceptional, (41)
"We enjoyed our stay!!"
United States
Hillary S.
The price is AU$932
includes taxes & fees
27 Oct - 28 Oct
Bear Creek Cabin
Comfortable Berkshires retreat on mtn resort, SISO
8.8 out of 10, Excellent, (6)
"Kind and responsive host."
United States
Javier
The price is AU$761
includes taxes & fees
26 Oct - 27 Oct
Comfortable Berkshires retreat on mtn resort, SISO
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$588
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is AU$468
includes taxes & fees
27 Oct - 28 Oct
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
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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Top Cheshire Hotel Reviews

Find out more about Cheshire

Everything you need to know about Cheshire holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cheshire holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cheshire holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cheshire. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cheshire holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cheshire holiday rentals we have selected for you start as low as AU$175 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cheshire rentals

At Expedia, we put the best Cheshire holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cheshire rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cheshire holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cheshire. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Amore Estate - beautiful room with many places to explore and relax in.: This holiday home rental outside of Cheshire offers an outdoor pool, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Cheshire?

Expedia has 4 holiday rentals for your stay in Cheshire.

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.