As a Bostonian who escapes to the Berkshires every year, I’ve experienced some of the coziest, most scenic vacation rentals in the region. From dreamy treehouses to cozy mountain cabins and peaceful lake houses, Western MA has no shortage of amazing Airbnb stays. I’m excited to share 24 of my absolute favorites—each one offering its own unique charm to enjoy the natural beauty of the Berkshires. Whether you’re craving adventure or relaxation, this list has something for everyone!
- To discover more amazing Berkshires vacation rentals, check out these related articles: 11 Best Airbnbs in Massachusetts, 15 Unique Airbnbs in New England, 24 Unique Airbnbs in Vermont & 19 coolest Airbnbs in the US.)
Otis, The Berkshires
Lakefront Otis Home – Art-Filled Retreat on Hayes Pond With Boats and Hot Tub
This place stopped me mid-scroll. It’s on 6 wooded acres right on Hayes Pond in Otis – you get a rowboat, a kayak, and a dock shared with herons and beavers. Inside it feels like someone’s carefully collected home, not a rental – art everywhere, vaulted ceilings with skylights, two wood-burning stoves with firewood provided, a telescope for clear Berkshires nights, and a sound system that runs through the whole house. Seasonal hot tub on the deck, screened-in porch for bug-free evenings. Tanglewood, Stockbridge, and Great Barrington are all within a short drive when you’re ready to leave – which you might not be.
The 24 Coolest Airbnbs in the Berkshires
Here are the best Berkshires Airbnbs by category, taking into account different amenities, trip types, and budgets. The subsequent sections will cover each listing in more detail.
- Top Overall: Berkshires Mountain Home
- Best Luxury Rental: Magical Country Retreat
- Most Romantic: Beautiful Mountain Cabin
- Best for Large Groups: The Taggart House
- Best Cheap Vacation Home: French-style Chalet
- Coolest Treehouse: Octagonal Treehouse
- Best Cabin: Beautiful Nature Cabin
- Best with a Pool: Luxury Berkshire Estate
- Top Winter Airbnb : Log Cabin Getaway
- Best Lake House: Cozy Retreat Lake Garfield
- Most Unique: Silo Studio Cottage Rental
Note: Some of the properties below are featured on both Airbnb and VRBO. For each listing, I’ve only included the link to the website with the cheapest rates.
1. Enchanted Tiny Tower
- 📍 Location: Tyringham, MA
- 💵 Price Per Night: $294/night
- 🛏️ Sleeps: 2 guests
- 🔥 Unique Features: Historic fairytale tower, canopied bed, babbling brook views
- 🌟 Perfect For: Romantic getaways 💕, solo retreats 🌿, creative escapes ✍️
Stay at the Enchanted Tiny Tower, a whimsical two-story hideaway on the historic Santarella Estate in the Berkshires. Once the summer studio of sculptor Henry Hudson Kitson, this 350 sq. ft. retreat is unlike anything else.
The main level offers a cozy sitting area, a French country–style kitchenette with a Ninja Foodi, induction cooktop, microwave, and a dining nook overlooking the brook.
Step outside and explore four acres of gardens, stone bridges, a lily pond, woodland trails, and a chiminea seating area—perfect for evenings under the stars.
Minutes from the Appalachian Trail and Tyringham Cobble, and just a short drive to Tanglewood, Jacob’s Pillow, and nearby towns like Lee and Stockbridge, this magical retreat is made for two.
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2. Charming Rustic Berkshire Getaway
- 📍 Location: Otis, MA
- 💵 Price Per Night: $380/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Cozy rustic top-floor flat, spacious living, digital guidebook
- 🌟 Perfect For: Couples 💑, small families 👨👩👧👦, nature lovers 🌿, weekend getaways 🏞️
This Charming Rustic Berkshire Getaway is a peaceful top-floor flat designed for relaxing after days spent exploring the Berkshires. Warm and welcoming, it’s a perfect base for hiking, skiing, or simply unplugging.
The home features two comfortable bedrooms—one king, one queen—a full kitchen, and an open-concept living and dining space. Large windows let in plenty of natural light, adding to the cozy atmosphere.
Nearby, enjoy lakes, ponds, and scenic trails, with Jacob’s Pillow and other local favorites just minutes away.
Guests also receive a digital guidebook packed with curated tips on the area’s best dining, shops, and activities, making your country retreat easy and stress-free.
3. Mountain & Lake View Home, Monterey, Massachusetts
- 👥 9 guests | 🛏️ 4 bedrooms | 💰 ~$810/night
- 🏔️ Hilltop lake house with Lake Garfield and mountain views from nearly every room
- 🍂 Best in: early to mid October for peak Berkshires color
- ♨️ Hot tub and fire pit overlooking the lake
Mountain & Lake View Home is at the top of a private road in Monterey, Massachusetts, with Lake Garfield and the mountains of the Southern Berkshires spread out below. Inside, the open great room has deep-seated sofas and a stereo with a record player, and the chef’s kitchen has stainless steel appliances plus an island that seats six. There’s one king bedroom and three queens, along with two bathrooms, and the upstairs bath (with a deep soaking tub) sits inside the primary suite and is shared with a guest room.
The lower deck is the highlight here, with a hot tub and fire pit facing the lake and a pergola bar with stools for watching the sunset. A screened sunroom tucked into the woods adds another spot to hang out, with a sectional and a table for four looking out over the water. Add a couple of hammocks and a grill to the mix, and I’d happily spend a long fall weekend here with a good book and a view of the colors changing across the lake.
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👉 Send me cheap 2026 flightsLake Garfield is about a 15-minute walk from the house, and Butternut ski area is a 10-minute drive. Great Barrington is 20 minutes away, Stockbridge and Lenox are about 25, and New York City and Boston are both roughly 2.5 hours by car. The house is at the end of a long gravel road that gets plowed once snow reaches four inches, and since there’s no landline and cell service varies by carrier, plan on using the fast Wi-Fi to stay connected.
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4. Mid-Century Glass Octagon Chalet
- 📍 Location: Otis, MA
- 💵 Price Per Night: $427/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Wrap-around glass windows, large private deck with firepit
- 🌟 Perfect For: Couples 💑, design lovers 🎨, nature seekers 🌲, quiet retreats 🕊️
The Mid-Century Glass Octagon Chalet is an architectural standout on seven private acres in the Berkshires. Floor-to-ceiling windows surround the home, bringing the forest views right to you.
Inside, the open-plan living area is anchored by a modern wood-burning fireplace and cozy lounge spaces. Watch movies on the projector from the double bed or unwind with a good book from the home’s curated library.
Outdoors, the wrap-around deck offers a grill, dining space, sun chairs, café lights, and a fire pit—perfect for relaxed evenings under the stars.
Located just 20 minutes from Great Barrington and close to Tanglewood and Jacob’s Pillow, this design-forward retreat offers nature, comfort, and quiet in equal measure.
5. Berkshire Mountain Eco Retreat, Lee, Massachusetts
- 👥 8 guests | 🛏️ 3 bedrooms | 💰 ~$480/night
- 🏡 Energy-efficient home on a country road between Lenox and Stockbridge
- 🍂 Best in: early to mid October for peak Berkshires color
- 🔥 Wood-fired hot tub, open year-round
Berkshire Mountain Eco Retreat is an energy-efficient home in Lee, set between Lenox and Stockbridge, and Architectural Digest named it one of the best Berkshires stays for a cozy weekend in August 2026. The main floor opens into a big kitchen and living area, and there are two full bathrooms, one with a freestanding tub. Two bedrooms have queen beds, while an open loft upstairs holds two full-size Murphy beds for extra guests.
Out back, the private yard has a fire pit and a screened-in porch set up for outdoor dining. The wood-fired hot tub is unusual for a rental, and you’ll tend the fire yourself to keep it warm, which is half the fun. Stoking the fire and then sinking into a hot soak on a crisp October night sounds like my ideal Berkshires evening.
Great Barrington is 15 minutes away, and concerts at Tanglewood and plays at Shakespeare & Co. are a short drive from the house. The host also points to three ski mountains within minutes, plus the Kripalu yoga retreat and Canyon Ranch spa right around the corner. Keep an eye out for bears, since one guest spotted one over morning coffee, and note the gravel walkway and full staircase to the second floor if anyone in your group has mobility concerns.
6. Moose Lodge
- 📍 Location: Great Barrington, MA
- 💵 Price Per Night: $1,708/night
- 🛏️ Sleeps: 14 guests
- 🔥 Unique Features: 7,500 sq. ft. log cabin, game room with poker & blackjack tables
- 🌟 Perfect For: Large families 👨👩👧👦, ski groups ⛷️, reunion trips 🎉
Moose Lodge is a 7,500 sq. ft. log cabin tucked away in the Berkshires—perfect for family gatherings or group getaways. This spacious lodge delivers a mix of comfort, fun, and classic cabin charm.
Inside, relax in two cozy living areas, catch a movie in the private theater, or take on friendly competition in the game room with poker, blackjack, billiards, and foosball. With six bedrooms and seven bathrooms, there’s space for everyone to spread out.
Outdoors, fire up the grill in the outdoor kitchen, unwind on the patio, or gather around the fire pit under the stars.
When it’s time to explore, hit the slopes at Butternut or Catamount, hike nearby trails, or visit Downtown Great Barrington for local shops and dining.
7. Charming Home with Stunning Views
- 📍 Location: Lenox, MA
- 💵 Price Per Night: $1,514/night
- 🛏️ Sleeps: 8 guests
- 🔥 Unique Features: 6000 sq ft, en suite bedrooms, soaring great room, gourmet kitchen
- 🌟 Perfect For: Culture lovers 🎼, family getaways 👨👩👧👦, romantic retreats 💫
Stay just steps from Tanglewood at this charming home with stunning views—a 6,000 sq. ft. retreat designed for relaxing and reconnecting in the Berkshires.
The great room offers a fireplace and sweeping countryside views, while the gourmet kitchen flows into a sunny dining area with porch and deck access. Five en suite bedrooms provide comfort for all.
Walk to concerts at Tanglewood, or explore nearby cultural gems like Ventfort Hall, The Mount, and Downtown Lenox. Whether it’s a music-filled weekend or a quiet mountain escape, this home offers a peaceful base in every season.
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8. Hartsville Barn, New Marlborough, Massachusetts
- 👥 4 guests | 🛏️ 2 bedrooms | 💰 ~$315/night
- 🏡 Reconstructed 1860s horse barn beside a wild nature preserve
- 🍂 Best in: early to mid October for peak Berkshires color
- 🐕 Pets allowed
Hartsville Barn is an 1860s post-and-beam horse barn in New Marlborough, rebuilt as an open-concept retreat next to the Corn Warrior nature preserve. The great room pairs vintage furniture with an 8-seat pine table set against a backlit barn door, and the kitchen has an induction stove plus a cast iron farm sink. One king bed is on the main floor behind 10-foot linen curtains lined with blackout fabric, and the second king is up a spiral staircase in the loft, which means neither sleeping area has a door.
The loft has the best view in the barn, looking out into the trees of the preserve from under an uplit, hand-stained pine ceiling. Downstairs, the bathroom has an 1890s clawfoot tub with a shower, and outside, a fire pit with Adirondack chairs sits in a sunken clearing off the big grassy side yard. I’d start every morning with coffee in the loft’s rocking chair, watching the leaves turn over the preserve.
Lake Buel is about a 10-minute walk from the barn, and an Appalachian Trail trailhead is just 4 minutes away by car. For dinner, the Old Inn on the Green is 6 minutes away, and downtown Great Barrington is 11. Hot water can slow down after back-to-back showers, and one guest recommends packing bug spray for evenings at the fire pit.
9. Cozy Berkshires Escape
- 📍 Location: Great Barrington, MA
- 💵 Price Per Night: $1,043/night
- 🛏️ Sleeps: 8 guests
- 🔥 Unique Features: Heated pool, gourmet kitchen, huge wrap-around porch
- 🌟 Perfect For: Families, remote workers, relaxation seekers
Tucked on a private 1.4-acre lot, this restored 1892 home balances classic charm with modern updates. It’s an ideal spot for families, small groups, or anyone looking for a peaceful work-from-home retreat.
Cook in the chef’s kitchen, unwind in the steam shower, or pedal on the Peloton bike. The wrap-around porch features hammocks and a fire pit for laid-back afternoons or cozy evenings.
Lounge by the heated pool, stroll through the gardens, or grill up a feast. Just minutes away, explore Downtown Great Barrington, Lake Mansfield, or the region’s scenic hiking trails.
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10. Spacious Getaway Home
- 📍 Location: Lanesborough, MA
- 💵 Price Per Night: $777/night
- 🛏️ Sleeps: 14 guests
- 🔥 Unique Features: Sauna, Jacuzzi, hiking trail, 4 fireplaces, outdoor firepit
- 🌟 Perfect For: Large families, groups, nature lovers, outdoor enthusiasts
This Berkshire retreat sits on 38 private acres with room for the whole group to relax and explore. Six bedrooms and 4.5 baths make it easy to gather comfortably, whether you’re planning a reunion or a weekend escape.
Multiple living areas offer space to play games, share meals, or just kick back by the fire. The home also includes a sauna, Jacuzzi, Ping Pong table, and even a private hiking trail.
Head to Jiminy Peak for skiing, hike Mount Greylock, or catch a concert at Tanglewood. After a day out, unwind by the outdoor fire pit or listen to the creek that runs through the property.
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11. Undermountain Lodge
- 📍 Location: Sheffield, MA
- 💵 Price Per Night: $623/night
- 🛏️ Sleeps: 12 guests
- 🔥 Unique Features: Mountain views, two ponds, firepit, expansive deck, rustic log interior
- 🌟 Perfect For: Large groups, nature lovers, families, peaceful getaway
Undermountain Lodge offers a peaceful Berkshires escape, nestled between two spring-fed ponds with panoramic mountain views. It’s a rustic retreat for families or friends looking to unplug and reconnect.
Gather around the stone fireplace, cook together in the spacious kitchen, or share meals in the dining room overlooking the water. The covered porch and deck create extra space for morning coffee or evenings under the stars.
Explore the local trails, ski at Catamount Mountain Resort, or check out nearby parks and waterfalls. Whether you’re enjoying the quiet or heading out for adventure, this lodge makes for a memorable stay.
12. Romantic and Secluded Berkshire’s Gem
- 📍 Location: New Marlborough, MA
- 💵 Price Per Night: $570/night
- 🛏️ Sleeps: 12 guests
- 🔥 Unique Features: Secluded log cabin, three porches, garden, forest views
- 🌟 Perfect For: Couples ❤️, families 👨👩👧👦, nature lovers 🌲
This hidden log cabin sits on five private wooded acres, offering a peaceful setting year-round. Whether you’re planning a romantic weekend or a family getaway, this cozy retreat delivers both charm and seclusion.
The warm, wood-accented interior features four bedrooms and two baths, with plenty of gathering space by the fireplace or at the kitchen table. Multiple porches and a private garden add to the relaxing atmosphere.
Nearby, hike at Campbell Falls State Park, kayak at Harmon Pond, or dine in Great Barrington. Evenings are best spent by the fire pit, beneath the stars.
13. Stylish Mountain Home
- 📍 Location: Great Barrington, MA
- 💵 Price Per Night: $733/night
- 🛏️ Sleeps: 9 guests
- 🔥 Unique Features: Panoramic mountain & lake views, hot tub, screened sunroom
- 🌟 Perfect For: Families 👨👩👧👦, nature lovers 🌲, skiers 🎿, culture seekers 🎭
Take in panoramic lake and mountain views from this stylish Berkshires retreat, just 10 minutes from Butternut Ski Area. Thoughtfully designed, the home pairs modern comfort with the beauty of the outdoors.
The open-concept great room features cozy seating around the fireplace, plus games and a stereo for relaxed evenings. A chef’s kitchen with stainless appliances and a large island makes cooking for the group easy.
Unwind in the hot tub, gather by the fire pit, or enjoy quiet mornings in the screened sunroom. Whether you’re skiing, hiking, or catching a show at Jacob’s Pillow or Tanglewood, this home puts the best of the Berkshires at your fingertips.
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14. The Kemble Berkshires
- 📍 Location: Lenox, MA
- 💵 Price Per Night: $3,973/night
- 🛏️ Sleeps: 35 guests
- 🔥 Unique Features: Historic Gilded Age estate, 13 bedrooms, private bar, music room
- 🌟 Perfect For: Family reunions 👨👩👧👦, retreats 🧘♀️, weddings 💍, culture lovers 🎭
The Kemble is a grand 15,000 sq. ft. estate, originally built in the 1880s for a U.S. Secretary of State. Fully restored, this historic home now serves as a luxury venue for large gatherings and special events.
With 13 bedrooms and 14 bathrooms, there’s room for the entire group. Host dinners in the massive dining room, sip cocktails at the private bar, or gather in cozy spaces like the library and music room.
Walk to Downtown Lenox, visit Tanglewood, or explore The Mount and the Norman Rockwell Museum. From milestone celebrations to family gatherings, The Kemble delivers a one-of-a-kind Berkshires experience.
15. Charming Wooden Cottage
- 📍 Location: Monterey, MA
- 💵 Price Per Night: $218/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Sunroom with garden views, mature perennial gardens, carved wildflower path
- 🌟 Perfect For: Nature lovers 🌸, quiet retreats 🕊️, small families or couples ❤️
Escape to this peaceful wooden cottage perched above Lake Garfield. Bright and inviting, it features two bedrooms, two full baths, and a cozy living space with a new gas fireplace.
Sip coffee in the sunroom overlooking mature gardens or wander the carved wildflower path. The kitchen is fully equipped for easy meals, while the gazebo makes a perfect spot for morning relaxation.
In summer, swim or boat at Lake Garfield Beach, just a short drive away. For arts and culture, visit Tanglewood, Jacob’s Pillow, or the nearby towns of Great Barrington and Stockbridge. In winter, hit the slopes at Ski Butternut, just 12 minutes from the door.
Whether you’re seeking quiet moments in nature or a home base for Berkshires adventures, this cottage offers a relaxing retreat in every season.
16. Cozy Monterey Family Chalet
- 📍 Location: Monterey, MA
- 💵 Price Per Night: $220/night
- 🛏️ Sleeps: 6 guests
- 🔥 Unique Features: Wood-burning stove, screened porch, gas grill
- 🌟 Perfect For: Families 👨👩👧👦, outdoor lovers 🚶♂️, skiers ⛷️
This cozy family chalet has been a cherished getaway for nearly 20 years. The open-plan layout features a wood-burning stove, a well-stocked kitchen, and a bright dining area. Upstairs, the king bedroom and a twin room with a pull-out bed make sleeping arrangements easy.
Relax on the screened porch overlooking Loom Brook, or grill dinner on the deck. Spend summer days at Lake Garfield, just minutes away, or hike the Appalachian Trail right from the neighborhood.
Nearby Great Barrington and Monterey offer dining and shops. With fast Wi-Fi, child-friendly features, and a peaceful setting, this chalet is built for all-season family stays.
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17. Tranquility Glade, West Stockbridge, Massachusetts
- 👥 6 guests | 🛏️ 3 bedrooms | 💰 ~$550/night
- 🌲 Designer-renovated modern chalet on 5.5 private forest acres
- 🍂 Best in: early to mid October for peak Berkshires color
- 🔥 Stone fireplace under cathedral ceilings
Tranquility Glade is a modern chalet on 5.5 private forest acres in West Stockbridge, fully redesigned in 2023 with cathedral ceilings and a stone fireplace in the main living space. There are two king bedrooms and one queen, each with a luxury mattress topper, plus two full bathrooms, one with a double walk-in shower. A sleek European galley kitchen sits in the open-plan living area, and the lower level has a large den with a TV and games alongside an office nook.
Skylights fill the chalet with natural light all day, and the views from inside are nothing but trees. The wooden deck has plenty of seating and a Weber propane grill, with a fire pit nearby for roasting marshmallows after dark. I’d plan at least one slow morning here with the fire going and the leaves changing outside.
Tanglewood is 3.6 miles away (about a 6-minute drive), with Kripalu at 4.1 miles and Lenox and the Norman Rockwell Museum each 4.3 miles out. For hiking, Stevens Glen is 0.6 miles from the house and Olivia’s Overlook on North Yukon Ridge is 1.4 miles, while No. 6 Depot Café & Roastery in the village is a favorite coffee stop among past guests. Once snow arrives, you’ll need 4WD or AWD to make it up the road, and the steep loft stairs by the kitchen are off-limits to guests.
18. The Taggart House
- 📍 Location: Stockbridge, MA
- 💵 Price Per Night: $1,137/night
- 🛏️ Sleeps: 12 guests
- 🔥 Unique Features: 1850 historic estate, ballroom, riverside lawn, sunroom
- 🌟 Perfect For: Family reunions 👨👩👧👦, history lovers 🏛️, Berkshires getaways 🍂
The Taggart House is an 1850 estate set on three private acres along the Housatonic River. With six en-suite bedrooms and a chef’s kitchen, this historic home offers a refined blend of classic charm and modern comfort.
Spend your days unwinding in the sunroom, hosting dinners in the ballroom, or relaxing by the riverside fire pit. The landscaped garden and riverfront lawn create the perfect setting for morning coffee or evening cocktails.
Take a short stroll into town to explore local shops, cafés, and cultural landmarks. Visit the Norman Rockwell Museum, walk the grounds of Naumkeag, or attend an event at Tanglewood just a few minutes away.
Gather with loved ones for a special occasion or simply settle in for a relaxing weekend—The Taggart House is your invitation to experience the Berkshires in style.
19. Forget-Me-Not, Monterey, Massachusetts
- 👥 12 guests | 🛏️ 4 bedrooms | 💰 ~$1,110/night
- 🏞️ Three-story modern lake house above Lake Garfield with a private dock
- 🍂 Best in: early to mid October for peak Berkshires color
- 🚫 No pets, and guests must be 25+ to book
Forget-Me-Not is a three-story modern lake house in Monterey, set right above the shore of Lake Garfield with unobstructed views across the water. Vaulted ceilings rise over the main living room and huge windows pull light into the open kitchen, while the lower level adds a second living room with a kitchenette and a pool table. Two of the three king bedrooms have ensuite bathrooms, and a fourth room with two twin-over-full bunks shares a Jack-and-Jill bath with the third king, which works well for families traveling together.
A sunroom leads out to a big deck with a grill and an outdoor dining table looking over the lake. Having both a hot tub and a sauna is a rare combo for a lake rental, and the ground-level area below the deck is set up for ping pong and cornhole. Coffee on the private dock with fall color reflecting off the water would be my first move here.
The public beach on Lake Garfield is close by, and the host’s list of local attractions includes the Norman Rockwell Museum and the Mahaiwe Performing Arts Center. Past guests say the nearest coffee shop is about 10 minutes away and groceries are closer to 20, and one suggests bringing food with you when you arrive. The paved driveway is steep enough that it’s only suitable for 4WD or AWD vehicles (especially in winter), and there’s parking for about six cars between the driveway and the other side of the road.
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20. Exotic Mountain Retreat
- 📍 Location: Monterey, MA
- 💵 Price Per Night: $1,599/night
- 🛏️ Sleeps: 15 guests
- 🔥 Unique Features: Custom log home, wood-burning stove, private hot tub
- 🌟 Perfect For: Large families 👨👩👧👦, group retreats 🌲, nature lovers 🏞️, skiers 🎿
Gather your group at this custom-built log home, set in the peaceful Berkshire Mountains. With five bedrooms—including a first-floor primary suite—this spacious retreat accommodates up to 15 guests with room to relax and reconnect.
Soak in the private hot tub, unwind by the wood-burning stove, or cook together in the fully equipped kitchen. The surrounding trails and fishing spots invite outdoor adventure, while the Appalachian Trail is just a 10-minute drive.
Spend your days exploring Butternut Ski Mountain, browsing the shops in Great Barrington, or dining in Lenox. Whether you’re skiing, hiking, or simply enjoying downtime, this mountain hideaway is a welcoming base for your Berkshires escape.
21. The Playhouse
- 📍 Location: Lee, MA
- 💵 Price Per Night: $1,124/night
- 🛏️ Sleeps: 20 guests
- 🔥 Unique Features: Historic Vanderbilt estate, vaulted 25’ cathedral ceilings, lakefront access
- 🌟 Perfect For: Large families 👨👩👧👦, groups 👯♀️, art lovers 🖼️, wellness retreats 🧘
Once part of a Vanderbilt estate, The Playhouse is a 7,000 sq ft home rich with history and character. With 25-foot cathedral ceilings and grand living spaces, this former entertainment hall once welcomed guests like Nikola Tesla and President McKinley.
Host family meals across two kitchens, gather for movie nights in one of the cozy lounges, or walk just eight minutes to enjoy private lakefront access. Solar panels and eco-friendly amenities keep this storied estate both luxurious and sustainable.
Spend your days exploring The Mount, catching a show at Jacob’s Pillow, or skiing at Jiminy Peak and Bousquet. At The Playhouse, gather with family and friends for a Berkshires escape that combines rich history with modern comfort.
22. Lenox Haus
- 📍 Location Lenox, MA
- 💵 Price Per Night $521/night
- 🛏️ Sleeps 6 guests
- 🔥 Unique Features: Mid-century modern design, rooftop solar, large deck
- 🌟 Perfect For Families 👨👩👧👦, design lovers 🎨, Tanglewood visitors 🎶, Berkshires retreats 🌄
Stay at Lenox Haus, a freshly renovated mid-century retreat set on a quiet cul-de-sac just minutes from downtown. This three-bedroom, two-bath home combines thoughtful design with everyday comfort.
The bright, open interior features stylish vintage furnishings, hardwood floors, and central A/C. Cook meals in the well-equipped kitchen with a gas stove, then relax by the fireplace or gather around the game table for cozy evenings in.
Step outside to a spacious deck with lounge seating and room for al fresco dining. When you’re ready to explore, you’ll find Tanglewood, The Mount, and Ventfort Hall nearby, along with local spas, ski resorts like Bousquet, and great shopping.
Whether you’re planning a family vacation or a weekend with friends, Lenox Haus offers a modern take on the classic Berkshires escape.
23. Spacious Berkshire Home
- 📍 Location: Sandisfield, MA
- 💵 Price Per Night: $350/night
- 🛏️ Sleeps: 8 guests
- 🔥 Unique Features: 30 private acres, 5,000 sq ft home, 3 fireplaces
- 🌟 Perfect For: Family reunions 👨👩👧👦, ski trips 🎿, artist retreats 🎨, nature lovers 🌲
Find room to roam at this architect-designed Berkshire home, set on 30 secluded acres of forest and meadow. With 5,000 square feet of living space, it’s built for relaxing, reconnecting, and entertaining.
The Great Room impresses with 28-foot ceilings, hardwood floors, and a centerpiece fireplace. A chef’s kitchen with a gas range and island opens into light-filled communal spaces where everyone can gather.
Though completely private, you’re just 20 minutes from Great Barrington, 30 minutes to Tanglewood, and close to Jacob’s Pillow, scenic trails, and local lakes. Spend your days skiing, hiking, or simply enjoying the view from a cozy chair by the fire.
This peaceful retreat offers the space and setting for memorable Berkshires stays.
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24. Gingerbread House Tower
- 📍 Location: Tyringham, MA
- 💵 Price Per Night: $466/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Storybook tower bedchamber, fairytale gardens, koi pond & brook
- 🌟 Perfect For: Romantic getaways 💫, creatives & dreamers 🎨, nature lovers 🌲
Step into a storybook at the Gingerbread House Tower, part of the whimsical Santarella Estate in the Berkshires. This enchanting two-story hideaway surrounds you with lush gardens, lily ponds, and charming architecture.
Inside, unwind in a cozy living space filled with vintage details, natural light, and a hanging chair for lazy afternoons. A hidden full bed provides tucked-away comfort, while the tower loft features a dreamy queen canopy bed.
Wander the four-acre grounds, cross stone bridges, and gather around the fire pit beneath the stars. Spend the day exploring nearby towns like Lee, Lenox, Stockbridge, and Great Barrington, all just a short drive away.
For dreamers, creatives, and anyone craving a unique escape, the Gingerbread House Tower is pure magic.
- Read Next: 35 Best Hidden Vacation Spots in the US
Top Berkshires Airbnb: Coolest Rentals in Berkshire County MA
Have you ever stayed in a unique Airbnb or vacation rental in the Berkshires? Let me know in the comments or on Insta, as I’m always looking to add to this list of the most unique Airbnbs in the Berkshires!
Looking for more cool New England adventures? Check out these dreamy destinations:
– Coolest Airbnb Rentals in Massachusetts
– Unique Airbnbs in the White Mountains
– Best Airbnbs in Rhode Island
For further reading, check out my other New England and East Coast articles:
Global Viewpoint is a personal blog. All content is for informational and entertainment purposes only and does not constitute professional financial, medical, or legal advice.
