Rolling hills, rambling gardens, and mornings that begin with mist rising over a quiet pond—yes, we’re still in Massachusetts, but these Berkshires retreats might just convince you otherwise. From clawfoot tubs and crackling fireplaces to wildflower-filled meadows and weathered stone patios, these dreamy homes channel all the cozy, romantic charm of the English countryside—no passport required.
Whether you’re planning a slow weekend of tea and novels, a group gathering with farmhouse feasts, or an escape filled with fresh air and footpaths, this list has something to suit your pastoral mood. Pair your stay with visits to quaint museums, botanical gardens, and historic villages—because the Berkshires are positively brimming with charm.
Ready to live out your countryside fantasy? Let’s take a tour of six swoon-worthy stays:
- Sunny Pond
- Whitney
- Cordelia
- Chester
- Wellspring
- Half Moon
If you are looking for things to do while in the Berkshires, read our guide for more ideas.
Sunny Pond
9 Bedrooms | Sleeps up to 18 Guests
If Mr. Darcy had traded in Pemberley for a pond view and a Peloton, it might look a lot like Sunny Pond. Nestled ever so elegantly amongst the trees, this charming Berkshires estate offers English countryside vibes with a splash of New England.
By day, you will want to wander through the garden paths, lounge beside the glistening pond, or glide across the water in a pedal boat. By night, gather ‘round the fire pit for s’mores, storytelling, and your best countryside ghost tale.
Whether you’re sipping coffee on the dock, planning an elegant dinner under the chandelier, or simply watching the fog roll across the pond at dawn, Sunny Pond is your countryside fairytale brought to life.
Best Features:
• Private swimmable pond with dock, pedal boats & island access
• Movie room, game room, gym & guest house add-on
• Chef’s kitchen with two dishwashers, two ovens & double islands
• Outdoor fire pit, wraparound lawn, and nature trails
• Feels like a Britain period drama—but with WiFi
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Whitney
5 Bedrooms | Sleeps 12 Guests
Trade your daily grind for the fresh country air at this private retreat, where comfort and charm are practically doing a Morris dance. Right then, chaps, because Whitney isn’t just a place for a kip but a vacation home that makes you lose track of the days (in a good way, mind you).
You, on a screened patio, probably having a jolly good go at the foosball table while the Berkshires put on a splendid autumnal display just for your viewing pleasure. Whitney’s grounds? So sprawling, you might need a map and a packed lunch to explore the whole kit and caboodle. Don’t fret, though, the views are absolutely cracking.
Take a breath, let the serene surroundings work their magic, and enjoy your stay in this quintessential countryside escape.
Best Features:
- Large yard and field offering privacy and outdoor fun
- Screened patio with foosball, seating, and mountain views
- Comfy living room with a fireplace for relaxed evenings
- Cozy dining area and breakfast nook
- Nearby hiking, museums, and winter sports in the Berkshires
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Cordelia
5 Bedrooms | Sleeps 12 Guests
Head out to the back garden of Cordelia to discover a brick patio and a picturesque dining table just begging for a picture-perfect repast that even your Instagram followers will be ever so impressed.
The inside of this Massachusetts cottage welcomes you with a fireplace and telly in the front parlour – perfect for a bit of relaxation after a long day exploring. There’s also a rather grand dining room for more formal dinners, and a proper country kitchen with some interesting antique bits and bobs.
You’ll feel like you’ve stepped straight into a Jane Austen novel with the Berkshires absolutely brimming with outdoor pursuits, views that’ll knock your wellies off.
Best Features:
- Brick patio with dining table and fire pit for cozy nights
- Relaxing hammock for those peaceful moments
- Country-style kitchen with antique flair
- Clawfoot tub for a luxurious soak after a day of exploring
- Plenty of space with spacious bedrooms and a cozy vibe throughout
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Chester
4 Bedrooms | Sleeps 12 Guests
Prepare to be utterly smitten with Chester! This country abode in the peaceful village of Austerlitz, NY, is just the ticket for a proper getaway. The expansive windows are the stunner in offering views for miles that’ll make you feel like you’re starring in your own landscape painting.
An inviting fireplace perfect for toasting your tootsies after a bracing walk, a proper dining area for when you’re feeling a tad grand, and a kitchen that would make even the poshest chef feel right at home are but a few of the many delights that make this home a veritable paradise.
When you fancy a change of scenery, pop over to Chester for more outdoor capers, views to write home about, delightful hikes, and enough museums and art to keep you going.
Best Features:
- Stunning landscape views
- Outdoor deck with BBQ grill
- Large backyard for lounging under the sun
- Cozy fireplace and formal dining area
- Expansive deck patio with al fresco table and lounge seating
- Peaceful location just a short drive to Berkshire attractions
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Wellspring
7 Bedrooms | Sleeps 12 Guests
Wellspring is the sort of place you’d read about in a novel – a grand hideaway boasting views of the surrounding mountains that are simply peerless. Bask in the natural light and enjoy a gentle zephyr, perhaps with a spot of afternoon tea.
Evenings can be whiled away on the capacious patio as you get the barbecue going (weather permitting, naturally), enjoy a spot at the outdoor table whilst savouring the surrounding vistas, and perhaps indulge in a bit of stargazing.
Set on a substantial private plot, offering the utmost peace and quiet, offer your group a Berkshire experience that’ll be the talk of the town.
Best Features:
- Indoor pool with sunroom and lounge area (can be heated for an additional fee)
- Mountain views and a sense of true seclusion
- Lofted game space for a fun evening
- Outdoor patio with grill and dining area
- Fireplace in the living room
Book on Airbnb | Book on AvantStay Direct (Best Price)
Half Moon
4 Bedrooms | 8 Guests
Fancy a bit of a breather amidst the leafy knolls of the Berkshires? Then, Half Moon is your proper woodsy retreat for escaping the madding crowd. Don’t let the charmingly rustic log cabin exterior fool you, though, as the inside is as chic as you like, a delightful surprise akin to finding a perfectly ripe strawberry in a punnet of slightly squashed ones.
Modern decor and a kitchen that’s as colourful as a bag of Skittles create the perfect setting for a bit of jolly camaraderie at home, where playful connection is practically mandatory. Drink in the fresh country air from the spacious deck, complete with oodles of comfy spots to perch and watch the world, or at least the squirrels, go by.
Tucked beneath a canopy of trees at the end of a long winding drive, this hideaway is brimming with privacy, and all the conveniences one could wish for – a true gem indeed in the Berkshires.
Best Features:
- Wrap-around deck with outdoor dining and sun loungers
- Open concept and modern living space
- Fireplace for cozy nights with the fam
- BBQ grill for roasting nights
- Fully equipped kitchen, even with washer and dryer
- Comes with card games and extra bedding
Book on Airbnb | Book on AvantStay Direct (Best Price)
Related Reads:
- 35+ Best Things To Do in the Berkshires Year-Round
- 8 Homes That’ll Make You Feel Like You’re in Europe
- The 10 Best Fall Foliage Destinations in the USA
Where to Go in the Berkshires
If you are finally booking that Berkshires trip after finishing that English novel and a cup of afternoon tea, here are our top local attraction picks that you may want to add to your itinerary.
Berkshire Botanical Gardens
Step into a living postcard at Berkshire Botanical Gardens, where 24 acres of manicured beds and whimsical pathways showcase the very best of flora. Open since 1934, this seasonal haven is bursting with color from spring through fall—perfect for a meandering morning walk, a bit of gardening inspiration, or just pretending you’ve stumbled into a Jane Austen adaptation.
Bidwell House Museum
History and charm go hand in hand at the Bidwell House Museum, a lovingly preserved colonial home nestled on 192 acres of forest and gardens. Take a guided tour and step back into the 1700s, where stone hearths, wide-planked floors, and stories of early life await. Bonus points if you picnic on the lawn and channel your inner transcendentalist.
Mahaiwe Performing Arts Center
A cultural gem in the heart of Great Barrington, the Mahaiwe Performing Arts Center brings music, theatre, film, and comedy to the Berkshires in a stunningly restored 1905 venue. Whether it’s a Broadway-caliber show or an indie film screening, it’s the kind of place where you dress up just because—and every seat feels like the best one in the house.
Norman Rockwell Museum
Celebrate classic Americana with a visit to the Norman Rockwell Museum, home to the world’s largest collection of the beloved artist’s work. Located in Stockbridge (Rockwell’s hometown), this museum offers an intimate look into his studio, process, and timeless depictions of small-town life. It’s equal parts nostalgic, inspiring, and downright delightful.
Hancock Shaker Village
Step into another world at Hancock Shaker Village, a beautifully preserved Shaker settlement complete with an iconic round stone barn, heritage gardens, and working farm animals. Learn about Shaker innovation, simplicity, and craftsmanship as you explore this peaceful property—then pick up some handmade goods at the shop to bring a bit of that old-world charm home.
Historic Deerfield
A true time capsule of early American life, Historic Deerfield is a village-sized museum made up of lovingly restored 18th- and 19th-century homes. With costumed interpreters, hands-on exhibits, and period furnishings galore, it’s the perfect spot for history lovers, curious kids, and anyone craving a stroll through the past (with ice cream nearby, of course).
Jiminy Peak Mountain Resort
Whether you’re carving down the slopes or soaking in the mountain views with a cider in hand, Jiminy Peak is a four-season playground for outdoor enthusiasts. Hit the trails in winter for skiing and snowboarding, or come summer for ziplining, hiking, and mountain coaster rides. Either way, there’s a cozy après spot waiting for you at the bottom.
Time to Pack Your Wellies
If you’re craving slow mornings with tea by the fire or long walks through leaf-crunching trails, the Berkshires is your Old English dream come true. Pack your weekend bags, book the cottage, cue the Jane Austen playlist, and let the countryside work its magic!