Compare Western Massachusetts Chalets

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Featured Western Massachusetts 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.

Western Massachusetts Ski Accommodation

    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 Jan 4 to Jan 5
    $141 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    8.6/10 Excellent! (2,168 reviews)
    The Yankee, Trademark Collection by Wyndham

    The Yankee, Trademark Collection by Wyndham

    461 Pittsfield Rd Lenox MA
    $71 nightly
    The price is $79 total per night from Dec 24 to Dec 25
    $79 total
    Dec 24 - Dec 25
    Total with taxes and fees
    9/10 Wonderful! (1,000 reviews)
    Berkshire Valley Inn

    Berkshire Valley Inn

    2541 Hancock Rd Williamstown MA
    $139 nightly
    The price is $155 total per night from Jan 4 to Jan 5
    $155 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    9/10 Wonderful! (564 reviews)
    Jiminy Peak Mountain Resort

    Jiminy Peak Mountain Resort

    37 Corey Rd Hancock MA
    $174 nightly
    The price is $195 total per night from Dec 18 to Dec 19
    $195 total
    Dec 18 - Dec 19
    Total with taxes and fees
    8.2/10 Very Good! (987 reviews)
    Hampton Inn & Suites Berkshires-Lenox

    Hampton Inn & Suites Berkshires-Lenox

    445 Pittsfield Rd Lenox MA
    $107 nightly
    The price is $120 total per night from Jan 4 to Jan 5
    $120 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    9/10 Wonderful! (999 reviews)
    Monument Mountain Motel

    Monument Mountain Motel

    247 Stockbridge Rd Great Barrington MA
    $67 nightly
    The price is $74 total per night from Dec 18 to Dec 19
    $74 total
    Dec 18 - Dec 19
    Total with taxes and fees
    8.8/10 Excellent! (804 reviews)
    Shaker Mill Inn

    Shaker Mill Inn

    2 Oak Street West Stockbridge MA
    $102 nightly
    The price is $112 total per night from Dec 18 to Dec 19
    $112 total
    Dec 18 - Dec 19
    Total with taxes and fees
    9.6/10 Exceptional! (408 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
    $135 nightly
    The price is $151 total per night from Jan 4 to Jan 5
    $151 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    9.2/10 Wonderful! (758 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    One West Street Pittsfield MA
    $94 nightly
    The price is $105 total per night from Dec 19 to Dec 20
    $105 total
    Dec 19 - Dec 20
    Total with taxes and fees
    8/10 Very Good! (988 reviews)

Hotel Options in Western Massachusetts

    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 Jan 4 to Jan 5
    $141 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    8.6/10 Excellent! (2,168 reviews)
    MGM Springfield

    MGM Springfield

    One MGM Way Springfield MA
    $169 nightly
    The price is $192 total per night from Jan 4 to Jan 5
    $192 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    8.8/10 Excellent! (1,456 reviews)
    D. Hotel Suites & Spa

    D. Hotel Suites & Spa

    1 Country Club Rd Holyoke MA
    $128 nightly
    The price is $143 total per night from Dec 17 to Dec 18
    $143 total
    Dec 17 - Dec 18
    Total with taxes and fees
    9.2/10 Wonderful! (2,256 reviews)

Chalets

Book the best chalets in Western Massachusetts
Take a break from reality and kick back in a Western Massachusetts 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 Western Massachusetts. 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 Western Massachusetts has to offer.

Bring the whole group, because you’ll find plenty of space to spread out at Western Massachusetts 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.

Western Massachusetts Chalets essential information

Accommodation
3 Chalets
Lowest Price
$74
Highest Price
$195
Popular accommodation
Little Longbow Lakefront Chalet, Sunny Chalet Nestled in the Woods of Ashfield, Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut

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