Photo by Ed Gaffny

Cheshire Holiday Rentals

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Our top choices for Cheshire holiday rentals

3.0 star property
8.8 out of 10, Excellent, (2197)
"I great place to stay!!"
United Kingdom
Maricel
The price is NZ$219
includes taxes & fees
14 Jan - 15 Jan
Vacation Village in the Berkshires

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is NZ$410
includes taxes & fees
14 Jan - 15 Jan
Jiminy Peak Mountain Resort
10.0 out of 10, Exceptional, (28)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
The price is NZ$255
includes taxes & fees
4 Jan - 5 Jan
Getaway Near Mass MoCA, Great Hiking, Scenic Views

Holiday Home in Florida

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 NZ$637
includes taxes & fees
5 Jan - 6 Jan
Florida Mountain Log Cabin
2.0 star property
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 NZ$422
includes taxes & fees
2 Jan - 3 Jan
Penthouse Apartment on Park Street
9.4 out of 10, Exceptional, (40)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
United States
Roy
The price is NZ$359
includes taxes & fees
2 Jan - 3 Jan
Charming Apt in 18th c Berkshire Farmhouse
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is NZ$646
includes taxes & fees
5 Jan - 6 Jan
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Camping in Williamstown

Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is NZ$391
includes taxes & fees
14 Jan - 15 Jan
Huttopia Berkshires

Cabin in Charlemont

Bear Creek Cabin
10.0 out of 10, Exceptional, (43)
"We enjoyed our stay!!"
United States
Hillary S.
The price is NZ$1,034
includes taxes & fees
11 Jan - 12 Jan
Bear Creek Cabin
10.0 out of 10, Exceptional, (2)
"as advertised."
United States
Joshua G.
The price is NZ$1,391
includes taxes & fees
1 Feb - 2 Feb
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
10.0 out of 10, Exceptional, (1)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is NZ$733
includes taxes & fees
3 Jan - 4 Jan
Riverbend Berkshire East Basecamp - 3 bedrooms available
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is NZ$424
includes taxes & fees
3 Jan - 4 Jan
Berkshires Apartment at the Stephentown Hotel
9.8 out of 10, Exceptional, (35)
"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.
The price is NZ$760
includes taxes & fees
5 Jan - 6 Jan
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
The price is NZ$283
includes taxes & fees
4 Jan - 5 Jan
2 Twin beds on 1st floor with En-suite bathroom.
9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is NZ$787
includes taxes & fees
4 Jan - 5 Jan
Sun Filled Lenox Retreat - Minutes to Tanglewood!
10.0 out of 10, Exceptional, (13)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
The price is NZ$316
includes taxes & fees
1 Feb - 2 Feb
Taborton Harvest Boulder Pines Cabin in the woods
8.6 out of 10, Excellent, (34)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is NZ$519
includes taxes & fees
4 Jan - 5 Jan
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Holiday Home in Florida

The Greylock Cabin
10.0 out of 10, Exceptional, (5)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveller
The price is NZ$707
includes taxes & fees
27 Jan - 28 Jan
The Greylock Cabin
2.0 star property
The price is NZ$1,123
includes taxes & fees
5 Jan - 6 Jan
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is NZ$524
includes taxes & fees
6 Jan - 7 Jan
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 favorite 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 depends 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 NZ$219 per night. Entering your travel dates in the search wizard you might find 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?

Peace and quiet on the lake: This holiday home rental outside of Cheshire is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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.