Sheffield Vacation Homes

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Featured Vacation Homes in Sheffield

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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.

Hotel Options in Sheffield

    Wilder House Berkshires

    Wilder House Berkshires

    48 S Main Street Sheffield MA
    $180 nightly
    The price is $201 total per night from May 27 to May 28
    $201 total
    May 27 - May 28
    Total with taxes and fees
    9.8/10 Exceptional! (49 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $113 nightly
    The price is $126 total per night from May 25 to May 26
    $126 total
    May 25 - May 26
    Total with taxes and fees
    9/10 Wonderful! (946 reviews)
    Berkshires Untold

    Berkshires Untold

    194 Pittsfield Rd Lenox MA
    $119 nightly
    The price is $133 total per night from May 25 to May 26
    $133 total
    May 25 - May 26
    Total with taxes and fees
    9/10 Wonderful! (958 reviews)

Sheffield Vacation Homes

Book vacation homes in Sheffield
Next time you take a group getaway top Sheffield, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Sheffield vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Sheffield vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Sheffield; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Sheffield rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Sheffield is sure to be a winner.

Sheffield Vacation Homes essential information

Accommodation
434 Vacation Homes
Lowest Price
$126
Highest Price
$358
Popular accommodation
Peace and quiet on the lake, Cozy Riverside Berkshires Retreat, Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight., Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires! , Home in Great Barrington, Beautiful retreat in a lake community to the enjoy the summer season. , Spacious Home nestled along the Blackberry River in Northwest CT, Dock is waiting! Fishing, paddleboards, kayaking!! Come relax by the Lake!, Bluebird Valley Farmhouse

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