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 $130 per night from Apr 6 to Apr 7
    $130
    includes taxes & fees
    $116 per night
    Apr 6 - Apr 7
    9.4/10 Exceptional! (697 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    One West Street, Pittsfield, MA
    The price is $116 per night from Apr 11 to Apr 12
    $116
    includes taxes & fees
    $104 per night
    Apr 11 - Apr 12
    7.8/10 Good! (763 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr, Pittsfield, MA
    The price is $144 per night from Apr 4 to Apr 5
    $144
    includes taxes & fees
    $129 per night
    Apr 4 - Apr 5
    8.8/10 Excellent! (447 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
$116
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