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
    $86 nightly
    The price is $96 total per night from Nov 2 to Nov 3
    $96 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.6/10 Excellent! (2,028 reviews)
    The Yankee, Trademark Collection by Wyndham

    The Yankee, Trademark Collection by Wyndham

    461 Pittsfield Rd, Lenox, MA
    $134 nightly
    The price is $150 total per night from Nov 2 to Nov 3
    $150 total
    Nov 2 - Nov 3
    Total with taxes and fees
    9/10 Wonderful! (1,001 reviews)
    Berkshire Valley Inn

    Berkshire Valley Inn

    2541 Hancock Rd, Williamstown, MA
    $185 nightly
    The price is $207 total per night from Nov 3 to Nov 4
    $207 total
    Nov 3 - Nov 4
    Total with taxes and fees
    9/10 Wonderful! (562 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 19 to Oct 20
    $166 total
    Oct 19 - Oct 20
    Total with taxes and fees
    8.2/10 Very Good! (979 reviews)
    Hampton Inn & Suites Berkshires-Lenox

    Hampton Inn & Suites Berkshires-Lenox

    445 Pittsfield Rd, Lenox, MA
    $134 nightly
    The price is $150 total per night from Nov 4 to Nov 5
    $150 total
    Nov 4 - Nov 5
    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 Nov 2 to Nov 3
    $74 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.8/10 Excellent! (759 reviews)
    Shaker Mill Inn

    Shaker Mill Inn

    2 Oak Street, West Stockbridge, MA
    $132 nightly
    The price is $145 total per night from Nov 3 to Nov 4
    $145 total
    Nov 3 - Nov 4
    Total with taxes and fees
    9.6/10 Exceptional! (398 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! (738 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! (887 reviews)

Hotel Options in Western Massachusetts

    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd, Williamstown, MA
    $86 nightly
    The price is $96 total per night from Nov 2 to Nov 3
    $96 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.6/10 Excellent! (2,028 reviews)
    MGM Springfield

    MGM Springfield

    One MGM Way, Springfield, MA
    $179 nightly
    The price is $203 total per night from Oct 7 to Oct 8
    $203 total
    Oct 7 - Oct 8
    Total with taxes and fees
    8.8/10 Excellent! (1,416 reviews)
    La Quinta Inn & Suites by Wyndham Springfield MA

    La Quinta Inn & Suites by Wyndham Springfield MA

    100 Congress Street, Springfield, MA
    $119 nightly
    The price is $135 total per night from Oct 13 to Oct 14
    $135 total
    Oct 13 - Oct 14
    Total with taxes and fees
    8/10 Very Good! (1,271 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
$207
Popular accommodation
Little Longbow Lakefront Chalet, Sunny Chalet Nestled in the Woods of Ashfield, Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach

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