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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.


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.

Hotel Options in Pittsfield

    Holiday Inn & Suites Pittsfield-Berkshires

    Holiday Inn & Suites Pittsfield-Berkshires

    One West Street, Pittsfield, MA
    The price is $98 per night from Mar 8 to Mar 9
    4/5Very Good! (10 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires
    Best Western Plus Berkshire Hills Inn & Suites

    Best Western Plus Berkshire Hills Inn & Suites

    1350 W Housatonic St, Pittsfield, MA
    The price is $96 per night from Mar 10 to Mar 11
    4.1/5Very Good! (49 reviews)
    Best Western Plus Berkshire Hills Inn & Suites
    Hotel On North

    Hotel On North

    297 North Street, Pittsfield, MA
    The price is $130 per night from Mar 7 to Mar 8
    4.6/5Wonderful! (7 reviews)
    Hotel On North