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
    The price is $127 per night from May 18 to May 19
    $127
    includes taxes & fees
    $114 per night
    May 18 - May 19
    8.6/10 Excellent! (1,798 reviews)
    The Yankee, Trademark Collection by Wyndham

    The Yankee, Trademark Collection by Wyndham

    461 Pittsfield Rd, Lenox, MA
    The price is $120 per night from May 4 to May 5
    $120
    includes taxes & fees
    $107 per night
    May 4 - May 5
    9/10 Wonderful! (1,001 reviews)
    Berkshire Valley Inn

    Berkshire Valley Inn

    2541 Hancock Rd, Williamstown, MA
    The price is $110 per night from May 13 to May 14
    $110
    includes taxes & fees
    $99 per night
    May 13 - May 14
    9/10 Wonderful! (538 reviews)
    Jiminy Peak Mountain Resort

    Jiminy Peak Mountain Resort

    37 Corey Rd, Hancock, MA
    The price is $150 per night from May 4 to May 5
    $150
    includes taxes & fees
    $134 per night
    May 4 - May 5
    8.2/10 Very Good! (928 reviews)
    Hampton Inn & Suites Berkshires-Lenox

    Hampton Inn & Suites Berkshires-Lenox

    445 Pittsfield Rd, Lenox, MA
    The price is $160 per night from May 26 to May 27
    $160
    includes taxes & fees
    $143 per night
    May 26 - May 27
    9.2/10 Wonderful! (999 reviews)
    Monument Mountain Motel

    Monument Mountain Motel

    247 Stockbridge Rd, Great Barrington, MA
    The price is $85 per night from May 5 to May 6
    $85
    includes taxes & fees
    $76 per night
    May 5 - May 6
    8.8/10 Excellent! (710 reviews)
    Shaker Mill Inn

    Shaker Mill Inn

    2 Oak Street, West Stockbridge, MA
    9.6/10 Exceptional! (381 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
    The price is $169 per night from May 26 to May 27
    $169
    includes taxes & fees
    $151 per night
    May 26 - May 27
    9.2/10 Wonderful! (697 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    One West Street, Pittsfield, MA
    The price is $111 per night from May 28 to May 29
    $111
    includes taxes & fees
    $99 per night
    May 28 - May 29
    7.8/10 Good! (777 reviews)

Hotel Options in The Berkshires

    Life House Berkshires

    Life House Berkshires

    194 Pittsfield Rd, Lenox, MA
    The price is $115 per night from May 4 to May 5
    $115
    includes taxes & fees
    $103 per night
    May 4 - May 5
    9/10 Wonderful! (573 reviews)
    Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

    Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

    190 Meadow Street, South Lee, MA
    The price is $134 per night from May 14 to May 15
    $134
    includes taxes & fees
    $120 per night
    May 14 - May 15
    9/10 Wonderful! (627 reviews)
    The Yankee, Trademark Collection by Wyndham

    The Yankee, Trademark Collection by Wyndham

    461 Pittsfield Rd, Lenox, MA
    The price is $120 per night from May 4 to May 5
    $120
    includes taxes & fees
    $107 per night
    May 4 - May 5
    9/10 Wonderful! (1,001 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
$85
Highest Price
$169
Popular accommodation
Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut., Little Longbow Lakefront Chalet