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 $111 per night from Jan 5 to Jan 6
    $111
    includes taxes & fees
    $99 per night
    Jan 5 - Jan 6, 2025
    7.8/10 Good! (701 reviews)
    Best Western Plus Berkshire Hills Inn & Suites

    Best Western Plus Berkshire Hills Inn & Suites

    1350 W Housatonic St, Pittsfield, MA
    The price is $105 per night from Jan 2 to Jan 3
    $105
    includes taxes & fees
    $94 per night
    Jan 2 - Jan 3, 2025
    8.4/10 Very Good! (1,000 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr, Pittsfield, MA
    The price is $204 per night from Jan 1 to Jan 2
    $204
    includes taxes & fees
    $185 per night
    Jan 1 - Jan 2, 2025
    8.8/10 Excellent! (417 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
341 Vacation Homes
Lowest Price
$105
Highest Price
$223
Popular accommodation
Spectacular views and close to Great Barrington., Berkshire Village Carriage House - Super Private!!, Berkshire Ski House on Lake Garfield w/HT By Great Barrington , Beautiful Berkshire Farm House on 160+ Acres, Peace and quiet on the lake, Private Estate, Heated YEARROUND Outdoor Pool, Quintessential 6-BR Berkshires Lodge, 3 Bedroom Lakefront Home with Hot Tub & Fireplace, Amore Estate - beautiful room with many places to explore and relax in.