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

    Hotel On North

    Hotel On North

    297 North Street, Pittsfield, MA
    The price is $122 per night from Apr 27 to Apr 28
    $122
    includes taxes & fees
    $109 per night
    Apr 27 - Apr 28
    9.4/10 Exceptional! (707 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    One West Street, Pittsfield, MA
    The price is $115 per night from Apr 27 to Apr 28
    $115
    includes taxes & fees
    $103 per night
    Apr 27 - Apr 28
    7.8/10 Good! (774 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr, Pittsfield, MA
    The price is $133 per night from May 11 to May 12
    $133
    includes taxes & fees
    $119 per night
    May 11 - May 12
    8.8/10 Excellent! (457 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
444 Vacation Homes
Lowest Price
$115
Highest Price
$1,035
Popular accommodation
Berkshire Village Carriage House - Super Private!!, Hancock Village Inn at Jiminy Peak, 4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi, Spectacular views and close to Great Barrington., Peace and quiet on the lake, Lakeside Retreat Just You, The Lake & The View!, Secluded Lux Mansion Pool Home with Amazing Views, Heart of Lenox Walk to Town Cozy Cottage!, Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna