Book Holiday Homes in Cheshire
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Featured Holiday Homes in Cheshire

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

Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown

Stockbridge Village in Summer

Spacious 5-bedroom house in charming Lee with WiFi

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

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Contemporary Berkshire Home with Views of Taconic Golf Course

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

General Williams Estate House Lenox/Stockbridge
Cheshire Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Cheshire vacation homes are the perfect way for you to wing it.
Holiday houses in Cheshire let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Cheshire in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Cheshire adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Cheshire with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Cheshire vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Cheshire Holiday Homes essential information
Accommodation | 311 Holiday Homes |
---|---|
Lowest Price | NZ$213 |
Highest Price | NZ$1,445 |
Popular accommodation | Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown, Stockbridge Village in Summer, Spacious 5-bedroom house in charming Lee with WiFi, Amore Estate - beautiful room with many places to explore and relax in., Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, Contemporary Berkshire Home with Views of Taconic Golf Course, Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location, General Williams Estate House Lenox/Stockbridge |
Top trending hotels in Cheshire

Vacation Village in the Berkshires

Berkshire Mountain Lodge

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Hotel Downstreet, an Ascend Collection Hotel
More ways to explore Cheshire
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^Subject to availability and chosen travel dates.