Photo by Ed Gaffny

Search Holiday Rentals in Cheshire

    price find illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Save instantly and earn perks with One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Top Holiday Rentals in Cheshire

2.5mi from the lake! Fire pit, arcade, yard games!

10.0 out of 10, Exceptional, (12)
"This place is immaculate and the host is responsive. We stayed here to ski in Mount snow which is about 25 minutes drive. We arrived later in the evening and the place was warm and cozy. "
The price is £387
includes taxes & fees
8 Jul - 9 Jul
2.5mi from the lake! Fire pit, arcade, yard games!

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

10.0 out of 10, Exceptional, (2)
"as advertised."
The price is £634
includes taxes & fees
7 Jul - 8 Jul
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

The price is £278
includes taxes & fees
8 Jul - 9 Jul
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is £117
includes taxes & fees
1 Jul - 2 Jul
Deluxe Queen Room with 2 Queen Beds

Spacious 5-bedroom house in charming Lee with WiFi

The price is £647
includes taxes & fees
2 Jul - 3 Jul
Spacious 5-bedroom house in charming Lee with WiFi

Two Brooks Lodge

3.0 star property
4.8 out of 10, (3)
"Strong dog smell, dirty shabby condition of interior surfaces. Obvious makeshift repairs, spongy floors, torn, flaking couch. Kitchen counter had multiple burn marks and some sticky substance, corner held down with duct tape. Screen door off tracks, laying against wall. Wife was stung by insect in the unit, had to go to hospital. We moved out after only 3 hours, and literally slept in the car rather than go back. Owner uncaring, rude and greedy. Slow to return security deposit. I've...
Two Brooks Lodge

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

9.0 out of 10, Wonderful, (29)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is £237
includes taxes & fees
1 Jul - 2 Jul
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Peaceful getaway nestled on 5.6 acres of old farmland in Bennington, VT

The price is £354
includes taxes & fees
27 Jun - 28 Jun
Peaceful getaway nestled on 5.6 acres of old farmland in Bennington, VT

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is £332
includes taxes & fees
30 Jun - 1 Jul
North Getaway Cottage

New Home - Heart of Williamstown 183

10.0 out of 10, Exceptional, (1)
"Great place to stay. House is brand new with plenty of room. Has 3 bedrooms plus a finished room in basement which is equivalent of a 4th room. Hiking and restaurants are close to the property. Plenty of parking. Highly recommend. Absolutely no complaints."
The price is £939
includes taxes & fees
30 Jun - 1 Jul
New Home - Heart of Williamstown 183

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

9.8 out of 10, Exceptional, (70)
"We had a wonderful stay, thank you! "
The price is £404
includes taxes & fees
29 Jun - 30 Jun
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Comfortable Berkshires retreat on mtn resort, SISO

9.6 out of 10, Exceptional, (4)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is £357
includes taxes & fees
29 Jun - 30 Jun
Comfortable Berkshires retreat on mtn resort, SISO

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is £823
includes taxes & fees
8 Jul - 9 Jul
Hancock Village Inn at Jiminy Peak

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is £293
includes taxes & fees
29 Jun - 30 Jun
Near Tanglewood: Historic Summer Retreat

Enchanting Cottage, Come Enjoy Nature!

10.0 out of 10, Exceptional, (1)
"If you want TV, this isnt for you, but if you want a quiet place to check away and relax it fits the bill wonderfully"
The price is £752
includes taxes & fees
5 Jul - 6 Jul
Enchanting Cottage, Come Enjoy Nature!

NEW RENO Historic Creamery in Berkshires w/hot tub

The price is £352
includes taxes & fees
30 Jun - 1 Jul
NEW RENO Historic Creamery in Berkshires w/hot tub

Glass Lake Cottage

The price is £500
includes taxes & fees
7 Jul - 8 Jul
Glass Lake Cottage
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Deluxe Queen Room with 2 Queen Beds: This holiday home rental outside of Cheshire is equipped with an outdoor pool, air conditioning and WiFi to help you feel comfortable during your stay.

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.