Compare Cheshire Cottage Rentals

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Featured Cottages in Cheshire

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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 Cheshire

    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $126 nightly
    The price is $141 total per night from Apr 13 to Apr 14
    $141 total
    Apr 13 - Apr 14
    Total with taxes and fees
    8.8/10 Excellent! (2,332 reviews)
    Hotel Downstreet, an Ascend Collection Hotel

    Hotel Downstreet, an Ascend Collection Hotel

    40 Main St North Adams MA
    $127 nightly
    The price is $142 total per night from May 10 to May 11
    $142 total
    May 10 - May 11
    Total with taxes and fees
    8.8/10 Excellent! (1,001 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $108 nightly
    The price is $120 total per night from May 11 to May 12
    $120 total
    May 11 - May 12
    Total with taxes and fees
    9/10 Wonderful! (901 reviews)

Cottages

Book a cottage in Cheshire
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Cheshire. 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 Cheshire better.

Cottage apartments in Cheshire 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 Cheshire
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 Cheshire 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 Cheshire 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 Cheshire. 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.

Cheshire Cottages essential information

Accommodation
80 Cottages
Lowest Price
$120
Highest Price
$1,875
Popular accommodation
The Clearing - Quiet - Close To Nature, Brookside cottage near the mountains and outdoor recreation, Charming historic cottage on scenic road to Mt. Greylock, Cozy cottage with pool, walking distance to lake, Beachwood Cottage, Private Lake Cottage on 3 acres w/350 sq. ft. deck , Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires, Berkshires farm, 30+ guests, 50 acres, Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

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