Compare Great Barrington Chalets

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Featured Great Barrington 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.

Great Barrington Ski Accommodation

    Monument Mountain Motel

    Monument Mountain Motel

    247 Stockbridge Rd, Great Barrington, MA
    The price is $74 per night from Dec 24 to Dec 25
    $74
    includes taxes & fees
    $67 per night
    Dec 24 - Dec 25
    8.8/10 Excellent! (687 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 $178 per night from Dec 25 to Dec 26
    $178
    includes taxes & fees
    $159 per night
    Dec 25 - Dec 26
    9.2/10 Wonderful! (675 reviews)
    Quality Inn

    Quality Inn

    372 Main Street, Rte 7 and Main Street, Great Barrington, MA
    The price is $94 per night from Dec 29 to Dec 30
    $94
    includes taxes & fees
    $85 per night
    Dec 29 - Dec 30
    8/10 Very Good! (1,000 reviews)
    Travelodge by Wyndham Great Barrington Berkshires

    Travelodge by Wyndham Great Barrington Berkshires

    400 Stockbridge Rd, Great Barrington, MA
    The price is $77 per night from Dec 29 to Dec 30
    $77
    includes taxes & fees
    $69 per night
    Dec 29 - Dec 30
    7.4/10 Good! (512 reviews)
    Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

    Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

    415 Stockbridge Rd, Great Barrington, MA
    The price is $140 per night from Jan 1 to Jan 2
    $140
    includes taxes & fees
    $125 per night
    Jan 1 - Jan 2, 2025
    8.8/10 Excellent! (577 reviews)
    The Little Lion

    The Little Lion

    506 Stockbridge Road, Great Barrington, MA
    The price is $85 per night from Jan 5 to Jan 6
    $85
    includes taxes & fees
    $76 per night
    Jan 5 - Jan 6, 2025
    8.6/10 Excellent! (442 reviews)
    The Old Inn On The Green

    The Old Inn On The Green

    134 Hartsville-New Marlborough Rd, New Marlborough, Great Barrington, MA
    The price is $308 per night from Dec 24 to Dec 25
    $308
    includes taxes & fees
    $292 per night
    Dec 24 - Dec 25
    9.2/10 Wonderful! (80 reviews)
    Lantern House Motel

    Lantern House Motel

    256 Stockbridge Road, Great Barrington, MA
    8.2/10 Very Good! (454 reviews)

Hotel Options in Great Barrington

    Quality Inn

    Quality Inn

    372 Main Street, Rte 7 and Main Street, Great Barrington, MA
    The price is $94 per night from Dec 29 to Dec 30
    $94
    includes taxes & fees
    $85 per night
    Dec 29 - Dec 30
    8/10 Very Good! (1,000 reviews)
    Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

    Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

    415 Stockbridge Rd, Great Barrington, MA
    The price is $140 per night from Jan 1 to Jan 2
    $140
    includes taxes & fees
    $125 per night
    Jan 1 - Jan 2, 2025
    8.8/10 Excellent! (577 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 $178 per night from Dec 25 to Dec 26
    $178
    includes taxes & fees
    $159 per night
    Dec 25 - Dec 26
    9.2/10 Wonderful! (675 reviews)

Chalets

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

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

Great Barrington Chalets essential information

Accommodation
5 Chalets
Lowest Price
$74
Highest Price
$308
Popular accommodation
Little Longbow Lakefront Chalet, Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut., Berkshire Chalet: Walk to Lenox. Mobility friendly, Amazing Views.Dog Friendly! , SRC-Hudson Valley/Berkshires Cultural Corridor, Majestic Lake Front Chalet