Cheshire Holiday Homes
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Featured Holiday Homes in Cheshire

Peace and quiet on the lake

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Mid Century Modern 4 bedroom home with sweeping mountain views in Williamstown

19th c. Barn in the Berkshires

Charming Berkshire Retreat-Minutes to Williamstown

3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome

120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views

Contemporary Berkshire Home with Views of Taconic Golf Course

Stylish remodeled 2 bedroom property in enchanting Shelburne Falls Village.

Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay
Holiday Accommodation Cheshire
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Cheshire are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Cheshire itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Cheshire holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Cheshire, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Cheshire with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
Cheshire Holiday Homes essential information
Accommodation | 234 Holiday Homes |
|---|---|
Lowest Price | NZ$183 |
Highest Price | NZ$374 |
Popular accommodation | Peace and quiet on the lake, Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, Mid Century Modern 4 bedroom home with sweeping mountain views in Williamstown, 19th c. Barn in the Berkshires, Charming Berkshire Retreat-Minutes to Williamstown, 3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome, 120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views, Contemporary Berkshire Home with Views of Taconic Golf Course, Stylish remodeled 2 bedroom property in enchanting Shelburne Falls Village., Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay, Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included, Secluded Family Getaway w/ On-Site Creek in Hawley |
Top trending hotels in Cheshire

Berkshire Mountain Lodge
^Eligibility requirements and conditions apply









