Holiday Rentals in Cheshire

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Our top choices for Cheshire holiday rentals

3.0 star property
8.8 out of 10, Excellent, (2,204 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is €109
includes taxes & fees
21 Jan - 22 Jan
Vacation Village in the Berkshires
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is €331
includes taxes & fees
26 Jan - 27 Jan
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
9.6 out of 10, Exceptional, (4 reviews)
"Great property and location for a visit to Shelburne Falls. "
United States
Kevin K.
Spacious Ground Floor 2/3 Bed private suite 5 minutes walk to Bridge of Flowers
10.0 out of 10, Exceptional, (13 reviews)
"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 €161
includes taxes & fees
14 Jan - 15 Jan
Taborton Harvest Boulder Pines Cabin in the woods

Camping in Williamstown

Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is €183
includes taxes & fees
15 Jan - 16 Jan
Huttopia Berkshires

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is €210
includes taxes & fees
14 Jan - 15 Jan
Jiminy Peak Mountain Resort
9.6 out of 10, Exceptional, (67 reviews)
"What a quaint and comfy place!"
United States
Lori A.
The price is €183
includes taxes & fees
14 Jan - 15 Jan
Cozy Rustic Apt in 18th c Berkshire Farmhouse
9.8 out of 10, Exceptional, (21 reviews)
"Absolutely perfect quiet get away to relax and recharge will be back! "
United States
Dana V.
The price is €449
includes taxes & fees
16 Jan - 17 Jan
Little Longbow Lakefront Chalet
The price is €154
includes taxes & fees
14 Jan - 15 Jan
2 Twin beds on 1st floor with En-suite bathroom.

Holiday Home in Florida

Florida Mountain Log Cabin
2.0 star property
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is €299
includes taxes & fees
14 Jan - 15 Jan
Florida Mountain Log Cabin
10.0 out of 10, Exceptional, (3 reviews)
"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 €221
includes taxes & fees
14 Jan - 15 Jan
Berkshires Apartment at the Stephentown Hotel
9.8 out of 10, Exceptional, (35 reviews)
"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 €380
includes taxes & fees
14 Jan - 15 Jan
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
10.0 out of 10, Exceptional, (1 review)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
The price is €243
includes taxes & fees
14 Jan - 15 Jan
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
8.6 out of 10, Excellent, (34 reviews)
"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 €240
includes taxes & fees
14 Jan - 15 Jan
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
3.0 star property
The price is €475
includes taxes & fees
14 Jan - 15 Jan
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
7.0 out of 10, Good, (2 reviews)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is €276
includes taxes & fees
11 Feb - 12 Feb
Charming 3-bedroom Cabin for nature lovers
2.0 star property
9.6 out of 10, Exceptional, (14 reviews)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is €214
includes taxes & fees
14 Jan - 15 Jan
Penthouse Apartment on Park Street

Holiday Home in New Lebanon

Near Tanglewood: Historic Summer Retreat
9.2 out of 10, Wonderful, (25 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is €316
includes taxes & fees
25 Jan - 26 Jan
Near Tanglewood: Historic Summer Retreat
10.0 out of 10, Exceptional, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is €519
includes taxes & fees
20 Jan - 21 Jan
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
10.0 out of 10, Exceptional, (1 review)
"The Allen House was a wonderful stay for my family and we cannot wait to go back! The view was incredible; the host was very approachable for questions; and there were lots of nice touches like ample dishes and silverware.Very spacious, clean and cared for location. "
United States
Annemarie M.
The price is €279
includes taxes & fees
17 Jan - 18 Jan
The Allen House historic North Adams Home in the Berkshire Mountains
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, apart-hotels, 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 €109 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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside of Cheshire offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Cheshire?

Expedia has 5 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.