Pittsfield Vacation Homes

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Featured Vacation Homes in Pittsfield

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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 Pittsfield

    Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

    Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

    One West Street, Pittsfield, MA
    The price is $118 per night from Jan 24 to Jan 25
    $118
    includes taxes & fees
    $106 per night
    Jan 24 - Jan 25
    7.8/10 Good! (725 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr, Pittsfield, MA
    The price is $186 per night from Jan 23 to Jan 24
    $186
    includes taxes & fees
    $169 per night
    Jan 23 - Jan 24
    8.8/10 Excellent! (423 reviews)
    Best Western Plus Berkshire Hills Inn & Suites

    Best Western Plus Berkshire Hills Inn & Suites

    1350 W Housatonic St, Pittsfield, MA
    The price is $114 per night from Jan 28 to Jan 29
    $114
    includes taxes & fees
    $102 per night
    Jan 28 - Jan 29
    8.4/10 Very Good! (1,000 reviews)

Pittsfield Vacation Homes

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

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

Pittsfield Vacation Homes essential information

Accommodation
342 Vacation Homes
Lowest Price
$114
Highest Price
$227
Popular accommodation
Berkshire Village Carriage House - Super Private!!, Peace and quiet on the lake, Charlemont Retreat on Chickley River w/ EV Charger, Spectacular views and close to Great Barrington., Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna, Beautiful Berkshire Farm House on 160+ Acres, Berkshires Lakefront Retreat , Amore Estate - beautiful room with many places to explore and relax in., Hearts Desire is a furnished whole house in a small, colorful garden center.