THE YANKEE INN’SWinter Activities
Plan the Perfect Berkshires Winter Weekend
Make the most of a Berkshires winter getaway at The Yankee Inn in Lenox, MA. This guide brings together ski days at Bousquet Mountain and nearby Jiminy Peak, cultural visits to the Norman Rockwell Museum and The Mount, and cozy evenings by the fire in our fireplace rooms. Balanced between adventure and relaxation, it's your ideal winter escape in the Berkshires.
Ice Skating in the Berkshires
Scenic Snow-Covered Landscapes
Snow-Covered Nature Around The Yankee Inn
A Winter Walk Across the Ice Edge
Winter Hiking in the Berkshires
Pause in the Snowy Trails
Slow Winter Evenings with Hot Cocoa
Winter Itinerary
A thoughtfully curated three-day winter escape at The Yankee Inn Lenox, blending cozy comfort, outdoor adventure, and the best of the Berkshires in every season.
Arrival & Fireside Comfort
3:00 PM – Check-in at the Yankee Inn
Warm up in your cozy room, many featuring gas fireplaces, plush bedding, and views of snow-covered pines.
5:00 PM – Dinner in Lenox Village
Head to Cello or Alta Restaurant & Wine Bar for a farm-to-table meal in a charming, candle-lit atmosphere.
7:00 PM – Hot Cocoa & Indoor Pool Time
Return to the Yankee Inn to enjoy a relaxing swim in the indoor heated pool, followed by hot cocoa in the lounge or snuggled up in bed by the fire.
Snow Adventures & Local Flavor
8:00 AM – Complimentary Hot Breakfast at the Inn. Start your day with a hearty breakfast featuring eggs, waffles, and fresh coffee — perfect fuel for a winter day.
9:30 AM – Ski or Snowboard at Bousquet Mountain (10 minutes away). Spend the morning on the slopes with skiing, snowboarding, or tubing at this family-friendly ski area.
1:00 PM – Lunch at Antimony. Warm up with seasonal soups, sandwiches, and local craft beer just a short drive from the mountain.
2:00 PM – Afternoon at the Norman Rockwell Museum (weather-friendly indoor activity)
Immerse yourself in world-renowned art and history while staying warm and inspired.
4:00 PM – Après-Ski Back at the Inn. Unwind in your room with a warm bath, a book by the fireplace, or a nap before dinner.
6:00 PM – Dinner & Drinks at Firefly Gastropub
Enjoy a cozy, relaxed meal with craft cocktails and a creative menu — just a few minutes from the Inn.
Slow Morning & Scenic Send-Off
8:30 AM – Breakfast at the Inn
10:00 AM – Winter Walk at Kennedy Park or Pleasant Valley Sanctuary (weather permitting)
Take a short, peaceful walk through snowy woods and spot winter birds and animal tracks. Snowshoe rentals available at the Arcadian Shop
11:00 AM – Check-out & Optional Spa Stop
Wrap up your winter retreat with a visit to Canyon Ranch or Kripalu Center for a massage, yoga class, or sauna session before heading home.
Ski & Stay Packages
Looking for the perfect winter getaway in the Berkshires? The Yankee Inn in Lenox, MA, is your cozy home base for ski season adventures. Warm up in one of our fireplace rooms after a day on the slopes, enjoy a complimentary hot breakfast each morning, and relax in our indoor pool and hot tub. Take advantage of our exclusive Ski & Stay Packages with nearby mountains—Bousquet Mountain and Jiminy Peak—and save while you play! Whether you’re hitting the trails or unwinding fireside, The Yankee offers comfort, value, and easy access to the best skiing in the Berkshires.
Two Awesome Ski Mountains Just Minutes Away...
Jiminy Peak - 25 min drive
Bousquet Mountain - 3 min drive
BOUSQUET MOUNTAIN
We’re teaming up with Bousquet Mountain this season to bring our guests exclusive savings on lift tickets, the perfect way to make the most of your Berkshires getaway. 3-minute drive from The Yankee!
Ticket Prices
At the Yankee - Advance Purchase Ski & Stay Deal
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8 Hr. Weekday | $35
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Weekend & Holiday | $65
* Must reserve in advance!
At Bousquet
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8 Hr. Weekday | $50
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Weekend & Holiday | $80-99
HOW TO BOOK:
1) To lock in the best deal (and guarantee your tickets),give us a call to reserve your lift ticket as soon as you reserve your room. 413-499-3700
2) Make sure to reserve the correct ticket for the day you plan to ski (see date chart below)
WHAT TO KNOW:
Lift tickets sell out fast, and same-day availability isn’t guaranteed, so be sure to book early!
Weekends:
Saturday & Sundays
Holiday Periods:
December 26, 2025 – January 2, 2026 (Christmas Break Week)
January 17– 19, 2026 (MLK Weekend)
February 14 – 22, 2026 (President’s Week
JIMINY PEAK
Make your Berkshires getaway unforgettable with exclusive Jiminy Peak lift-ticket savings available when you reserve in advance! 25-minute drive from The Yankee
Ticket Prices
At the Yankee - Advance Purchase Ski & Stay Deal
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8 Hr. any day | $100
* Must reserve in advance!
At Jiminy Peak
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8 Hr. Any Day | $124
HOW TO BOOK:
1) To lock in the best deal (and guarantee your tickets),
2) Give us a call to reserve your lift tickets as soon as you reserve your room. 413-499-3700.
Dining & Local Favorites
From cozy wine bars to farm-to-table restaurants, the Berkshires offer a vibrant dining scene just minutes from The Yankee Inn. In Lenox Village and nearby towns, discover intimate, candle-lit spaces, seasonal menus, and locally sourced ingredients that reflect the region’s character. Whether it’s a relaxed lunch, a refined dinner, or a casual evening drink, each spot brings its own take on authentic Berkshires hospitality.
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01 /
34 Church St
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02 /
37 Church St
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03 /
71 Church St
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04 /
65 Church St
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05 /
55 Pittsfield Rd
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06 /
56 Church St
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