Holiday Rentals in Sheffield
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^
Check rental availability in Sheffield
Holiday Rentals in Sheffield

Antique Farmhouse Totally Restored

Guesthouse Cabin vacation rentals in Berkshire County

The Ponds at Foxhollow

Peace and quiet on the lake

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Private Estate, Heated Yearround Outdoor Pool

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Pristine Home In Becket Woods

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Private Access To Laurel Lake, Enjoy Lake Life

Remodeled Lakefront retreat!! Come join us for Ski Season!!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

Quintessential 6-BR Berkshires Lodge

Enjoy comfortable elegance in this secluded grand home located in town
Other types of properties in Sheffield you may be interested in

Wilder House Berkshires
Holiday Accommodation Sheffield
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 Sheffield 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 Sheffield itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Sheffield 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 Sheffield, 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 Sheffield 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.
Top Holiday Rental Destinations
More accommodation in Sheffield
Top 20 Sheffield Hotels
More destinations for you
^Eligibility requirements and conditions apply