Stockbridge Vacation Homes

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Featured Vacation Homes in Stockbridge

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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 Stockbridge

    The Red Lion Inn

    The Red Lion Inn

    30 Main Street Stockbridge MA
    $185 nightly
    The price is $207 total per night from May 31 to Jun 1
    $207 total
    May 31 - Jun 1
    Total with taxes and fees
    8.8/10 Excellent! (1,000 reviews)
    The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

    The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

    26 Glendale Road, RR 183 Stockbridge MA
    $358 nightly
    The price is $399 total per night from Jun 14 to Jun 15
    $399 total
    Jun 14 - Jun 15
    Total with taxes and fees
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $130 nightly
    The price is $145 total per night from May 31 to Jun 1
    $145 total
    May 31 - Jun 1
    Total with taxes and fees
    9/10 Wonderful! (958 reviews)

Stockbridge Vacation Homes

Book vacation homes in Stockbridge
Next time you take a group getaway top Stockbridge, 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 Stockbridge vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Stockbridge 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 Stockbridge; 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 Stockbridge 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 Stockbridge is sure to be a winner.

Stockbridge Vacation Homes essential information

Accommodation
415 Vacation Homes
Lowest Price
$145
Highest Price
$399
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, 19th c. Barn in the Berkshires, Incredible Estate: pool, pond, gym, arcade, trails & more! Ask about open dates!, 120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views, Spacious Home nestled along the Blackberry River in Northwest CT

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