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Berkshire House Stay, Lee, MA (2026)

09/05/2026

www.berkshirehousestay.com
Planning a scenic escape this fall? 🍁🚗 As we kick off our new series of classic Berkshire day trips, we’re starting right from our front door in Lee. Buckle up for this lovely autumn drive heading west into the historic towns and rolling hills toward the NY border.

Drop these exact stops into your Google Maps and you're ready to roll:
• Starving Artist or Lee's Corner Kitchen, Lee, MA
• Stockbridge Coffee and Tea, Stockbridge, MA
• First Congregational Church, Great Barrington, MA
• Hillsdale General Store, Hillsdale, NY
• Olde 1811 Antique Shoppe, Chatham, NY
• Balderdash Cellars, Richmond, MA
• Berkshire House Stay, Lee, MA

Lee ☕ Meet in Lee: Every great road trip needs a starting line, and beautiful Lee is the place to be. Meet up with your crew for a relaxed morning bite—whether that’s a sweet pastry at Starving Artist or a classic, hearty breakfast at Lee's Corner Kitchen—before we hit the scenic back roads.

Stop 1: Stockbridge Stroll & Shop 🍂 Historic Stockbridge: Park at Stockbridge Coffee & Tea to kick off your stop! Browse gifts at Side Tracks, walk over to the iconic Red Lion Inn to check out Shop Around the Corner, and stroll back up Main Street to pop into Whispered in the Heart, BerkCHEERS, and NeJaime’s—then loop back for a treat at the coffee shop. ✨ Not a shopper? Stroll west down Main Street to take in the historic homes, or walk over to Naumkeag to explore the stunning autumn gardens if you've got the energy!

Stop 2: Great Barrington 🚗 The Drive: Cruising south on Route 7 toward Great Barrington, keep your eyes peeled as Monument Mountain rises up right alongside the road, framed by incredible bursts of autumn color. 🍎 Harvest Stops & Great Barrington Stroll: Right on Route 7 as you head out of Stockbridge, make a quick stop at Windy Hill Farm to pick your own autumn apples or select a pumpkin for the season. Park near the First Congregational Church and head out on foot! Browse the unique finds at Fripperie and explore the charming local shops lining Main Street. Afterward, take a peaceful meander along the Riverfront Trail to watch the fall foliage drape over the Housatonic River. 🍔 Lunch Stop: Hop back in the car for a quick drive to Bistro Box (open through October!) to grab a fantastic outdoor lunch in the crisp autumn air before heading further west.

Stop 3: Hillsdale, NY 🚗 The Drive: The journey over to Hillsdale treats you to sweeping, open-air views of the valley as you wind through the Taconic Range and get closer to the New York border. 🛍️ Crossing into New York: Park in front of the Hillsdale General Store and spend a happy hour exploring—don’t forget to check out the antiques upstairs! Step right across the street to HG Kitchen for wonderful cookware and gadgets, and visit Books and Cake on the other side for a wonderfully curated read (and, of course, a sweet slice of cake). 🍎 C***r Stop: If you have time before heading out, make a quick detour over to Little Apple C***ry for a lovely afternoon tasting.

Stop 4: Chatham, NY 🚗 The Drive: Winding your way north from Hillsdale toward Chatham on classic two-lane roads, you glide right through the scenic Harlem Valley and its historic farm hamlets, surrounded by rolling hills draped in vibrant fall foliage. 👻 Historic Wandering in Chatham: Begin your Chatham stop at the Olde 1811 Antique Shoppe—housed in Chatham’s oldest building, it’s an absolute blast to explore (and especially atmospheric around Halloween!). Afterward, wander down Main Street to check out the unique local boutiques and treat your crew to something sweet at Fork and Whisk Bakery.

Stop 5: Balderdash Cellars 🚗 The Drive: Winding your way east from Chatham over toward Balderdash Cellars in Richmond takes you across some of the prettiest country roads in the region—drifting past quiet rural farmlands, over gentle ridges, and down into the peaceful valleys just west of the Berkshires' interior. 🍷 Final stop in Richmond: Make your way over to Balderdash Cellars in Richmond—one of our absolute favorites! Drop in to enjoy some fantastic w**e, live music and food trucks on most weekends, and the warmest hospitality from owners Donna, Christian, and their wonderful staff. It’s the ultimate spot to unwind together in the afternoon.

Berkshire House Stay 🏠 Your Home Base in the Berkshires: Why rush home when you can make a full weekend out of it? Located right in the center of Lee, Berkshire House Stay is the ultimate cozy headquarters for your group getaway. With plenty of space featuring 5 bedrooms and 5 baths, a fantastic private backyard, and a wonderful porch for morning coffee or evening unwinding, there is plenty of room for everyone to spread out and relax together. ✨ Ready to gather your crew? Share this post with your travel partners, plan your autumn escape, and come stay with us! Skip the platform fees and save 15% mid-week for Fall using code WEEKDAY15. Link in bio to book your stay directly with us!

09/03/2026

Labor Day weekend is here! Summer is winding down, but there's still plenty of fun across the Berkshires.

✨ Events & Highlights
09/04: 1st Friday Art Walk (Pittsfield) & The Mount Ghost Tour.
09/05: Norman Rockwell Walking Tour & Goat Yoga at Hancock Shaker Village.
All Weekend: Berkshire Museum Aquarium (newly updated), GB Historical Society Barn Sale, Barrington Stage (Noises Off), GB Public Theatre (Yellow Wallpaper) and Berkshire Busk (final weekend).

🍴 Our Go-To Food & Drink
Lee (Walk from us): The Mint (Sunday Brunch), Roses (biscuits), Lee’s Corner Kitchen.
Great Barrington: Number Ten (steaks/martinis), and Fiddleheads.
Lenox: Bea's (new) and Alta (w**e and food)

🎸 Live Music Catch live sets this weekend Friday: Seven Wonders (Stationary Factory),
Saturday: E.T.E. (The Foundry), Alabama Shakes (Tanglewood), Grateful Dead All Stars (Buttonball Barn) and Dan Hamilton at Balderdash!

🎨 ART adventure
The Wit “Dorothy of OZ” by Ceravolo
Gallerie271 A Walk in the Woods All Wknd
Hall Gallery at JWS Be MEIP Art Exhibit
Ozzie’s Glass Gallery Hand Crafted Glass
Good Purpose Gallery Icons of the Berkshires
Bernay Fine Art Summertime
Follow for all upcoming art events

🏠 Plan Your Group Stay: Looking for your group base? Save 15% mid-week for fall with code WEEKDAY15.

www.berkshirehousestay.com

08/27/2026

Your Berkshire Escape Awaits! 🏡✨
Summer is winding down, but the magic in the hills is just getting started for the weekend of August 28–30. Whether you are planning a group getaway, a fall foliage preview, or a cozy winter escape, gather your favorite people and make our spacious home your local basecamp.

Here is everything happening across the county this weekend:

✨ Special Events & Fair Fun:
Catch the classic Cummington Fair all weekend long, take a ghost tour at The Mount, enjoy morning Goat Yoga at Hancock Shaker Village, or check out Museum Day at the Berkshire Museum.

🎭 Theater & Dance:
The region's iconic stages are keeping the energy high! Catch the Lucia di Lammermoor opera at The Mahaiwe, Hubbard Street Dance at Jacob’s Pillow, Noises Off at Barrington Stage, Hamlet at Shakespeare & Company, and more.

🎸 Live Music:
From Tanglewood open rehearsals to intimate shows, live tunes fill the hills all weekend: Tom Rush at The Guthrie Center, Wanda Houston at Balderdash Cellars, The BTU’s at Buttonball Barn, Rory Block at the Stationary Factory, and local favorite Michael Junkins & Friends at The Lion’s Den.

🎨 Art & Galleries:
Explore local creativity with the It’s a Riot reception in New Marlborough, The Line of It All at Art in the Berkshires Gallery, Tom Marosz's exhibit at The Wit, and hand-crafted glass at Ozzie's Gallery.

🛍️ Specialty Shopping:
Take a stroll through Stockbridge for artisan sweets at Peace, Love and Chocolate, specialty boutique finds at BerkCHEERS, upscale souvenirs, and w**e tastings at Nejaime’s W**e Cellar.

🍴 Good Food & Dining:
Work up an appetite and explore incredible local flavors! Walk right from our door in Lee to Agave’s Mexican or Station Gastropub, or head out to Once Upon a Table in Stockbridge, Pizzeria Boema in Lenox, and Steam Noodles in Great Barrington.

🥾 Hike of the Week & Day Trips:
Head out to Bear Swamp in Ashfield for 3 miles of gorgeous trail exploring—featuring wildflower glades, rugged lowlands, and grand summit views. (Pro tip: Pair it with a trip to the Cummington Fair the same day!)

🧗 Outdoor Adventures:
Our winter mountains are fully transformed into summer playgrounds! Hit the "Catamonster" zip line at Catamount, or ride the alpine and mountain coasters at Jiminy Peak and Berkshire East.

Ready to Experience It All?
Skip the heavy platform fees and book direct with us! Save 15% mid-speed / mid-week for Fall using code WEEKDAY15 at checkout. 🔗 Link on our page to reserve your dates!

08/25/2026

fall is when this place truly shows off. 🍂✨

From world-class culture at Tanglewood and Jacob’s Pillow to epic hiking trails, w**e tastings, and memories made with favorite people, the Berkshires are unforgettable. And the best part? You don't just have to visit—you can make our home your ultimate Berkshire basecamp. 🏡❤️

Here is why guests love staying with us:
• "A bedroom and bathroom for each couple made our stay an absolute luxury!"
• "The front porch is the ultimate spot for morning coffee and conversation."
• "A historic, spacious, spotlessly clean, and perfect base for exploring the Berkshires."
Peak autumn foliage season is right around the corner, and our fall dates are filling up fast. Ready to experience the magic of the Berkshires for yourself?

🍁 Save 15% on any mid-week stay this fall when you book direct using code WEEKDAY15.

🔗 Tap the link in our bio to check availability and book your stay at Berkshire House Stay!

Balderdash Cellars Visit Lenox Shakespeare & Company The Mount @

08/23/2026

As the summer crowds head home, this is our final mid-week guide of the season—and honestly, mid-week in the Berkshires is the best-kept secret in travel. Less traffic, shorter wait times, and pure autumn magic right around the corner. 🍂✨
Here is how to spend the ultimate mid-week getaway:
🌿 Monday:
• Start your week with a mindful Qigong session with Jamie Greene at The Mount
• Pick up a w**e and cheese board at Guido’s in Lenox
• Head over to the Berkshire Botanical Garden for Music Mondays and Mike Cobb and the Crevulators 🎶
🥾 Tuesday:
• Hit the trails at Questing Reservation in New Marlborough for a 1.5-mile loop past colonial ruins and up to Leffingwell Hill
• Enjoy a chef-driven dinner at The Station Gastropub in Lee (pro tip: grab a seat at the bar!)
• Catch an evening stage performance of Hamlet at Shakespeare & Company 🎭
🍎 Wednesday:
• Spend the afternoon apple picking and browsing the charming garden center at Windy Hill Farm
• Treat yourself to gourmet Japanese cuisine at Bizen (we recommend trying the Omakase!)
• Stretch those vocal cords for a fun night of karaoke at Buttonball Barn 🎤
✨ Thursday:
• Explore the historic residence, gardens, and outdoor sculpture exhibition at Chesterwood Studio 🎨
• Wind down with Sunset Yoga at Naumkeag, led by our favorite: Yoga Lee! 🧘‍♀️
• Grab dinner in the cozy tavern at The Red Lion Inn, then head downstairs for the Parlor Magic Show ✨
Fall foliage season is almost here, and our peak autumn dates are filling up fast! 🍁 Want a cozy, perfectly located group base just minutes from all these spots?
Save 15% mid-week this fall with code WEEKDAY15.
Come stay with us at Berkshire House Stay! 🔗
Tap the link in our bio to book your direct stay.

08/19/2026

This Weekend in the Berkshires What’s happening this week across the Berkshires! Summer is winding down, which means now is the perfect time to plan your crisp fall foliage trip or cozy winter escape. 🍂✨
Here is your weekend rundown:
✨ Events & Entertainment: Catch Berkshire Botanical Garden's Family Fridays, The Mount Ghost Tour, the Elizabeth Freeman Walk at Ashley House, goat yoga at Hancock Shaker Village, the opera at The Mahaiwe, or Astrology 101 at Ventfort Hall. Plus, world-class theater is running all weekend (Dear Alien, Ballet Hispanico, Noises Off, Clair de Lune & Hamlet, and more)!
🥾 Hike of the Week: Head up Dry Hill Reservation in New Marlborough for a picturesque, moderate 1.4-mile hike to a 1,750-foot peak featuring wetlands, dense forests, and sweeping southwest valley views.
🎸 Live Music: Enjoy weekend tunes from Antimony Brewery and Balderdash Cellars to The Guthrie Center, Buttonball Barn, and the Stationary Factory.
🍴 Good Food & Dining: Grab a bite right in Lee at Cafe Triskele or 51 Park, head to West Stockbridge for Acqua’al 2, try Olde Heritage or Brava in Lenox, or check out No Comply and GB Eats in Great Barrington.
🎨 Art & Shopping: Explore gallery receptions and local boutique finds around Lee, Lenox, and Great Barrington (including a stop at Hillsdale General Store!).
🏠 Stay With Us: Looking for your group base in the Berkshires? Our 5-bed/5-bath home is ready for you. Save 15% mid-week for Fall with code WEEKDAY15. Link in bio to book direct! 🔗

08/18/2026

🏠 Berkshire House Stay for your next family getaway! BOOK for Leaf Peeping Season!

Explore from our central location or just hang in the backyard with our BBQ and hammock.

Spread out with our living room, family room, game room !

🛌 With 5 bedrooms AND 5 bathrooms, everyone gets a real bed and their own space. No bathroom schedules or pull-out couches in the kitchen.

🚶‍♂️Send the early birds for a 5-minute stroll to Lee’s Corner Kitchen or Starving Artist. After breakfast do a little window shopping while the rest of the house sleeps in. Saturday Farmer's Market right at the square. And we always find something for the house at Finders Keepers!

Want some pastries delivered to go with the homecooked eggs from Highlawn Farm? for those tasty treats.

We are minutes away from the best of the Berkshires:
🎼 Stockbridge & Lenox: Just a quick hop for some additional strolling and shopping.

🎭Still Summer: We are perfectly positioned for your trips to Tanglewood (10 min) Jacob’s Pillow(15 min), and Shakespeare & Co. (10 min)

Or, choose between a BBQ in the backyard, with plenty of seating or a nice stroll to our favorites: Cafe Triskele, The Station or Agave.

🎲 Legendary Game Nights: Our shelves are stocked with the classics. Perfect for rainy afternoons or late-night tournaments.

We have some weekday availability this summer. Use code MIDWEEK15 at checkout when you book direct for 15% discount. Tag the organizer and tell them you found the spot. Link in Bio!

Valid for new direct bookings on stays through September 2026.

08/17/2026

What the Berkshire locals are doing when the weekend crowds head home...less traffic, shorter wait times, and some fantastic mid-week events. ( berkshirehousestay ) This week's recommendations:

Monday:
+A daytime trip to see the final summer blooms at the beautiful Bridge of Flowers in Shelburne, grabbing a coffee at Red Dalia Cafe
+Picnic prep stopping into Spirited W**es in Lenox for w**e and a cheese board, so you can enjoy:
+An evening of Music Mondays and Pulso de Barro at the Berkshire Botanical Garden 🎶

Tuesday:
+A daytime hike just outside of Lee at Tyringham Cobble, enjoying the lovely trail rising above the valley floor with panoramic views of the Berkshire hills
+Dinner at The Station Gastropub in Lee, housed in the former train station with a chef-driven menu (we like eating at the bar!), then
+An evening stage performance of Frankie & Johnny in the Clair de Lune (fresh and vulnerable!) at Shakespeare & Company (or Hamlet if you catch the matinee) 🎭

Wednesday:
+An afternoon stroll of shopping therapy in Great Barrington—starting at Friperie, wandering to Main Street and Barrington Outfitters, checking out the library, and crossing the street for Yellow House Books, One Mercantile, Coco’s Candy, and Karen Allen Fiber Arts—finished with a fun drink by the team at The Well
+A creative seasonal dinner in a beautiful location with an attentive staff at Gedney Farm in New Marlborough, followed by
+An evening performance of Huang Yi: INK or Ballet Hispanico at Jacob’s Pillow 🩰

Thursday:
+A daytime visit to the Chesterwood Studio to explore the residence, studio, gardens, and sculpture exhibition
+A special evening featuring Sunset Yoga at Naumkeag, led by our favorite: Yoga Lee! 🧘‍♀️ followed by
+Dinner at Once Upon a Table in Stockbridge for farm-to-table dining and friendly service, or grabbing dinner in the tavern at the Red Lion Inn and heading downstairs for live music 🍽️

Fall is just around the corner—start thinking about crisp air, stunning foliage, and leaf peeping in the Berkshires! 🍂

Enjoy the week! Next time, Come Stay berkshirehousestay

08/17/2026

What the locals are doing when the weekend crowds head home...
.. Enjoy the Berkshires with less traffic, shorter wait times, and some fantastic mid-week events. Swipe through for this week's recommendations:

Monday:
+A daytime trip to see the final summer blooms at the beautiful Bridge of Flowers in Shelburne, grabbing a coffee at Red Dalia Cafe
+Picnic prep stopping into Spirited W**es in Lenox for w**e and a cheese board, followed by
+An evening of Music Mondays and Pulso de Barro at the Berkshire Botanical Garden 🎶

Tuesday:
+A daytime hike just outside of Lee at Tyringham Cobble, enjoying the lovely trail rising above the valley floor with panoramic views of the Berkshire hills
+Dinner at The Station Gastropub in Lee, housed in the former train station with a chef-driven menu (pro tip: we like eating at the bar!), then
+An evening stage performance of Frankie & Johnny in the Clair de Lune (fresh and vulnerable!) at Shakespeare & Company (or Hamlet if you catch the matinee) 🎭

Wednesday:
+An afternoon stroll of shopping therapy in Great Barrington—starting at Friperie, wandering to Main Street and Barrington Outfitters, checking out the library, and crossing the street for Yellow House Books, One Mercantile, Coco’s Candy, and Karen Allen Fiber Arts—finished with a fun drink by the team at The Well
+A creative seasonal dinner in a beautiful location with an attentive staff at Gedney Farm in New Marlborough, followed by
+An evening performance of Huang Yi: INK or Ballet Hispanico at Jacob’s Pillow 🩰

Thursday:
+A daytime visit to the Chesterwood Studio to explore the residence, studio, gardens, and sculpture exhibition
+A special evening featuring Sunset Yoga at Naumkeag, led by our favorite: Yoga Lee! 🧘‍♀️ followed by
+Dinner at Once Upon a Table in Stockbridge for farm-to-table dining and friendly service, or grabbing dinner in the tavern at the Red Lion Inn and heading downstairs for live music 🍽️

Fall is just around the corner—start thinking about crisp air, stunning foliage, and leaf peeping in the Berkshires! 🍂

Enjoy the week! Next time, Come Stay Berkshire House Stay

08/16/2026

There’s nothing quite like an autumn morning in the Berkshires. ☕️ Crisp air, peak foliage, and plenty of space for your group to unwind.
And here is a taste of the fun:

Pumpkin Show - last year over 1500 pumpkins vying for your attention

-Apple picking, c***r tasting and fun

- Ghost 👻 tours

- more Ghost 👻 tours

- festivals, pumpkins and crafts!

Ready to experience it? Book your stay directly through our site and take 15% off any weekday visit. DM for code! Link in bio! 🏡✨

Berkshire House Stay

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