Compare The Berkshires Chalets

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Featured The Berkshires Chalets

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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.

The Berkshires Ski Accommodation

    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd, Williamstown, MA
    $112 nightly
    The price is $125 total per night from Oct 30 to Oct 31
    $125 total
    Oct 30 - Oct 31
    Total with taxes and fees
    8.6/10 Excellent! (2,086 reviews)
    The Yankee, Trademark Collection by Wyndham

    The Yankee, Trademark Collection by Wyndham

    461 Pittsfield Rd, Lenox, MA
    $127 nightly
    The price is $141 total per night from Nov 2 to Nov 3
    $141 total
    Nov 2 - Nov 3
    Total with taxes and fees
    9/10 Wonderful! (1,013 reviews)
    Berkshire Valley Inn

    Berkshire Valley Inn

    2541 Hancock Rd, Williamstown, MA
    $184 nightly
    The price is $206 total per night from Nov 6 to Nov 7
    $206 total
    Nov 6 - Nov 7
    Total with taxes and fees
    9/10 Wonderful! (563 reviews)
    Jiminy Peak Mountain Resort

    Jiminy Peak Mountain Resort

    37 Corey Rd, Hancock, MA
    $149 nightly
    The price is $166 total per night from Oct 21 to Oct 22
    $166 total
    Oct 21 - Oct 22
    Total with taxes and fees
    8.2/10 Very Good! (982 reviews)
    Hampton Inn & Suites Berkshires-Lenox

    Hampton Inn & Suites Berkshires-Lenox

    445 Pittsfield Rd, Lenox, MA
    $111 nightly
    The price is $124 total per night from Nov 16 to Nov 17
    $124 total
    Nov 16 - Nov 17
    Total with taxes and fees
    9/10 Wonderful! (1,002 reviews)
    Monument Mountain Motel

    Monument Mountain Motel

    247 Stockbridge Rd, Great Barrington, MA
    $67 nightly
    The price is $74 total per night from Nov 2 to Nov 3
    $74 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.8/10 Excellent! (771 reviews)
    Shaker Mill Inn

    Shaker Mill Inn

    2 Oak Street, West Stockbridge, MA
    $128 nightly
    The price is $140 total per night from Nov 2 to Nov 3
    $140 total
    Nov 2 - Nov 3
    Total with taxes and fees
    9.6/10 Exceptional! (399 reviews)
    Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

    Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

    249 Stockbridge Rd, Great Barrington, MA
    $143 nightly
    The price is $160 total per night from Nov 2 to Nov 3
    $160 total
    Nov 2 - Nov 3
    Total with taxes and fees
    9.2/10 Wonderful! (744 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)

Hotel Options in The Berkshires

    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd, Williamstown, MA
    $112 nightly
    The price is $125 total per night from Oct 30 to Oct 31
    $125 total
    Oct 30 - Oct 31
    Total with taxes and fees
    8.6/10 Excellent! (2,086 reviews)
    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)

Chalets

Book the best chalets in The Berkshires
Take a break from reality and kick back in a The Berkshires chalet on your next vacation. Stay right in the middle of all the action, but feel like you’re miles away. Be as active or as relaxed as you want. Your chalet is truly yours. No one can tell you what to do on your chalet stay—and it’s the best way to enjoy a getaway.

Get the most from your chalet stay
You’ll make incredible new memories at chalets in The Berkshires. They look great in your photos, with sunning backdrops and cozy touches like fireplaces and exposed beam ceilings. Wake up to light streaming through your big picture window and admire your incredible view. Don’t just look at the great outdoors, though. Get out there and experience all that The Berkshires has to offer.

Bring the whole group, because you’ll find plenty of space to spread out at The Berkshires chalet houses. Whether you use all those bedrooms for the kids or for your crazy crew, you can settle in quickly thanks to chalets’ convenient amenities. Whip up a meal in no time in the kitchen or kitchenette, or whip out your phone to call for delivery. Cozy up to the fire, or fire up the blender for some drinks. When you’ve got a chalet, it’s going to be good day.

The Berkshires Chalets essential information

Accommodation
2 Chalets
Lowest Price
$74
Highest Price
$206
Popular accommodation
Little Longbow Lakefront Chalet, Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach

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