Compare Pittsfield Cottage Rentals

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Featured Pittsfield Cottages

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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

    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr, Pittsfield, MA
    $113 nightly
    The price is $126 total per night from Nov 2 to Nov 3
    $126 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.8/10 Excellent! (716 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    One West Street, Pittsfield, MA
    $103 nightly
    The price is $115 total per night from Nov 2 to Nov 3
    $115 total
    Nov 2 - Nov 3
    Total with taxes and fees
    7.8/10 Good! (908 reviews)
    FairBridge Inn Express

    FairBridge Inn Express

    16 Cheshire Road, Pittsfield, MA
    $75 nightly
    The price is $84 total per night from Oct 26 to Oct 27
    $84 total
    Oct 26 - Oct 27
    Total with taxes and fees
    5.2/10 (798 reviews)

Cottages

Book a cottage in Pittsfield
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Pittsfield. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Pittsfield better.

Cottage apartments in Pittsfield range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Pittsfield
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Pittsfield and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Pittsfield cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Pittsfield. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Pittsfield Cottages essential information

Accommodation
108 Cottages
Lowest Price
$84
Highest Price
$126
Popular accommodation
The Clearing - Quiet - Close To Nature, Private Island - Largest Fresh Water Reservoir in Mass, Heaven Can't Wait, On Beautiful Kinderhook Lake!!, Waterfront Cottage 10 Min From Great Barrington, Charming historic cottage on scenic road to Mt. Greylock, Cozy cottage with pool, walking distance to lake, Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!, Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! , Charlemont Retreat on Chickley River w/ EV Charger

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