Sheffield house rentals

Choose one of our 586 vacation home rentals in Sheffield and you’ll have the ideal base for your next big adventure. Canann Village Historic District, North Canaan and East Canaan are among the city’s most popular neighborhoods.

Exactly where you stay, when you plan to travel and your trip length will determine how much you pay for a vacation home rental in Sheffield. Enter your travel details on Vrbo to compare options and then lock in the best one for you.

That can all depend on the type of weather you enjoy, along with other factors. Many visitors to The Berkshires stay in a Sheffield vacation home rental in May, when the average temperature ranges from 46ºF (8ºC) to 68ºF (20ºC).

When searching for your vacation home rental in Sheffield, make use of our “Location” filter. This will help you choose the types of areas you prefer to stay in, whether that’s near nature or somewhere close to the action.

Explore our weekend rentals and start packing for a memorable couple of days away. Our main tips for booking your ideal house in Sheffield? Stay flexible when searching and modify your dates until you find the vacation home rental that suits your needs.

With six pet-friendly vacation home rentals in Sheffield, you can enjoy your next adventure with your best friend right by your side. On top of a comfortable bed for everyone, plenty of houses also come with perks like fenced-in yards and complimentary dog treats. Find out what’s available by choosing the “Pets allowed” filter.

Planning a memorable escape to Sheffield means finding cool things for all ages to enjoy. Norman Rockwell Museum, Ski Butternut and Catamount Ski Area are just two of the options here. And Vrbo’s vacation home rentals are the perfect base for your sightseeing activities.

Booking your vacation home rental with Vrbo means you get the entire property to yourselves — your own private retreat, with no interruptions or distractions from anyone else. Also, our easy payment and cancellation policies give you the freedom to alter your plans if required. Plus, our One Key™ rewards program lets you earn OneKeyCash™* on any eligible bookings on Vrbo, Expedia and Hotels.com. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Hotels.com, Expedia and Vrbo.