Compare Pittsfield Cottage Rentals

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Featured Cottages 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

    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $113 nightly
    The price is $126 total per night from Dec 1 to Dec 2
    $126 total
    Dec 1 - Dec 2
    Total with taxes and fees
    Hotel On North

    Hotel On North

    297 North Street Pittsfield MA
    $119 nightly
    The price is $133 total per night from Nov 29 to Nov 30
    $133 total
    Nov 29 - Nov 30
    Total with taxes and fees
    9.6/10 Exceptional! (976 reviews)
    Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

    Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

    1055 South Street Pittsfield MA
    $103 nightly
    The price is $115 total per night from Nov 30 to Dec 1
    $115 total
    Nov 30 - Dec 1
    Total with taxes and fees
    9.2/10 Wonderful! (253 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
102 Cottages
Lowest Price
$115
Highest Price
$133
Popular accommodation
The Clearing - Quiet - Close To Nature, Cozy Cottage-Sunset On The Lake , Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! , Quiet Get Away on the Lake! Kayaks,life vests ,Fishing Equipments ,golf clubs, Private Island - Largest Fresh Water Reservoir in Mass, Heaven Can't Wait, On Beautiful Kinderhook Lake!!, LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE, Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires, Charming historic cottage on scenic road to Mt. Greylock

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