Berkshire Area Rentals
From $292 per night (USD)VRBO
Central Haus (Group getaway on a quiet street)
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Beautifully designed house on a lovely, quiet street, with a view of Mt. Greylock. Three-minute drive to MassMoCA, six-m ...
From $292 per night (USD)VRBO
From $407 per night (USD)Expedia
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Leave your busy schedule behind for a life of leisure at this vacation rental hideaway. This rustic 4-bed, 2-bath home i ...
From $407 per night (USD)Expedia
From $320 per night (USD)VRBO
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This ski-in, ski-out condo is located right at the base of the mountain in JJ’s Lodge in the heart of the village at Jim ...
From $320 per night (USD)VRBO
From $355 per night (USD)Expedia
Artist's Camp on Lake Mahkeenac
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Refurbished cottage, perfect for a couples getaway. This retreat is tastefully decorated with with local antiques & fres ...
From $355 per night (USD)Expedia
From $324 per night (USD)VRBO
51 Church Street, Lenox MA - One Bedroom Unit
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Refined getaway Newly renovated downtown space fully equipped for all your needs. The kitchen has an array of cooking es ...
From $324 per night (USD)VRBO
From $470 per night (USD)Expedia
Pristine Home In Becket Woods
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Peaceful home on two acres to come and enjoy nature and each other's company. The house features high ceilings ...
From $470 per night (USD)Expedia
From $544 per night (USD)VRBO
Modern Victorian Walk to Main Street
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Built in 1903, this updated and yet stunning example of Victorian craftsmanship is a perfect place for family and friend ...
From $544 per night (USD)VRBO
From $311 per night (USD)VRBO
Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 6
The Berkshire Gorge House is 15 minutes from Jiminy Peak Ski Area, 30 minutes to Bosquet’s Ski area in Pittsfield, an ho ...
From $311 per night (USD)VRBO
From $481 per night (USD)VRBO
Ashley Falls Home w/ Fire Pit: Hike & Ski!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Game Room | 2,734 Sq Ft | ~6 Mi to Campbell Falls State Park Whether you’re chasing waterfalls in the summer, leaf-peep ...
From $481 per night (USD)VRBO
From $363 per night (USD)VRBO
Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful Berkshire condo within Jiminy Peak grounds. First Corner unit in Country Villages past the Country Inn with am ...
From $363 per night (USD)VRBO
From $439 per night (USD)VRBO
Wooded Berkshire Cottage - Minutes from Lenox Village - A Year-Round Retreat!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy the Berkshires Tucked beside the woods and minutes from the heart of Lenox, this lovingly renovated 1950s cot ...
From $439 per night (USD)VRBO
From $1340 per night (USD)VRBO
Renovated family friendly house close to everything and endless views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Bright, comfortable house with pool and comfortable outdoor seating and eating areas, endless mountain views in front an ...
From $1340 per night (USD)VRBO
From $874 per night (USD)VRBO
Cozy escape in the trees of the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
We are thrilled to share our country escape with you and hope you enjoy it as much as we do. Set on 5 acres of land, wit ...
From $874 per night (USD)VRBO
From $365 per night (USD)Expedia
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Lakefront property with own dock on Otis Reservoir with beautiful views and garden. Great for fall foliage. For ski sea ...
From $365 per night (USD)Expedia
From $317 per night (USD)VRBO
Dancing Horse Lodge
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Dancing Horse Lodge is located on Horse Farm in the heart of the beautiful Berkshire Mountains with plenty of room for f ...
From $317 per night (USD)VRBO
From $456 per night (USD)Expedia
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Situated in the heart of the Berkshires, this 3-bed, 2-bath vacation rental offers a modern living space, a large yard a ...
From $456 per night (USD)Expedia
From $340 per night (USD)VRBO
Houghton Hill: Style and History in the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Enjoy fresh air and warm sun at the top of Houghton Street. And it's an 8-minute walk to MASS MoCA and the town center. ...
From $340 per night (USD)VRBO
From $997 per night (USD)VRBO
Lakeside Home With Pool-Completely Renovated
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
On beautiful Lake Pontoosuc, this 100% renovated home is complete with a heated outdoor pool! Every detail has been att ...
From $997 per night (USD)VRBO
From $855 per night (USD)VRBO
Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy the Jiminy Peak Mountain Resort and explore the Berkshires during Spring, Summer, and Fall in this highly desirabl ...
From $855 per night (USD)VRBO
From $228 per night (USD)Expedia
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Fireplace | Grill | Board Games & Puzzles Nestled in the woods of East Otis, this 2-bedroom, 1-bathroom vacation rental ...
From $228 per night (USD)Expedia
From $718 per night (USD)VRBO
Perfect for Winter Skiing!!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Perfect family home for all Winter activities with 4 Bedrooms and 3.5 baths, plus it is central to all the cultural act ...
From $718 per night (USD)VRBO
From $487 per night (USD)VRBO
12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Beautiful country home with 3 bedrooms plus a kids loft, 6 minutes to Great Barrington with lots to discover. 12 minutes ...
From $487 per night (USD)VRBO
From $195 per night (USD)VRBO
Summer in the Berkshires!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Spend the SUMMER in the HEART of the BERKSHIRES! JUST minutes from both the Lenox and Stockbridge Town Beach with access ...
From $195 per night (USD)VRBO
From $1945 per night (USD)VRBO
Charming, spacious country home with stunning views.....steps from Tanglewood!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Just steps to Tanglewood Main Gate and Kripalu from this dramatic three-story shingle style contemporary with five bedro ...
From $1945 per night (USD)VRBO
From $306 per night (USD)VRBO
Lovely Lakefront Cottage, Peaceful Setting, Hiking And More
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This lovely lakefront cottage has been a favorite family gathering place of ours for 30 years. It sits on picturesque Lo ...
From $306 per night (USD)VRBO
From $604 per night (USD)VRBO
NEWLY RENOVATED THREE BEDROOM HAUS IN LENOX WITH MODERN INTERIOR DESIGN.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Modern, bright and renovated. Mid Century vogue furnishings, hardwood floors and central A/C are just some features you ...
From $604 per night (USD)VRBO
From $339 per night (USD)VRBO
“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
One of the very few waterfront homes available for rent. What other houses offer you 150 feet private lakefront where ...
From $339 per night (USD)VRBO
From $614 per night (USD)VRBO
Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Location, Location, Location 4 BR, 3½ bath immaculate property in Lenox available as a short-term rental. A ten minute ...
From $614 per night (USD)VRBO
From $318 per night (USD)VRBO
Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Sweet, newly renovated cottage, in a blissfully tranquil setting on Lake Garfield in Monterey, MA. Secluded, private, ye ...
From $318 per night (USD)VRBO
From $395 per night (USD)VRBO
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Beautiful, spacious, 3 bedroom, 2 bathroom, family home in the Berkshires located on a private road on crystal clear Ric ...
From $395 per night (USD)VRBO
From $294 per night (USD)VRBO
Charming Downtown Williamstown Cottage - 5 Min Walk to Campus
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This beautifully restored small home in the heart of Williamstown is the perfect location for visitors to the attraction ...
From $294 per night (USD)VRBO
From $638 per night (USD)VRBO
Spectacular setting on your own private lake close to it all!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This is the perfect Berkshire home to swim, hike, leaf-peep, ski, sled, engage in the cultural attractions of the neighb ...
From $638 per night (USD)VRBO
From $513 per night (USD)VRBO
Designer Berkshire Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is what ‘Tiny Home’ Dreams are made of! Our Renovated Designer Cottage located in rural Richmond Massachusetts is c ...
From $513 per night (USD)VRBO
From $576 per night (USD)VRBO
Enchanted Cottage On Babbling Brook
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
This turn of the century cottage is located on a 130 acre farm, it has total privacy and beautiful surrounding. The hous ...
From $576 per night (USD)VRBO
From $540 per night (USD)VRBO
A Fun Farmhouse Near Ski Butternut
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our home is in the charming town of Great Barrington and its many unique shops and restaurants. It's very near mountains ...
From $540 per night (USD)VRBO
From $159 per night (USD)VRBO
Duplex in Historic Mill District Walkable to Williams & Spring St.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Up-and-coming neighborhood in the historic Mill Village district in Williamstown that is walkable to the Williams' campu ...
From $159 per night (USD)VRBO
From $573 per night (USD)VRBO
An In-Town Beauty with Late Checkout
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Berkshires and all its attractions are at your doorstep in this newly renovated, well-insulated 1900 Victorian, situ ...
From $573 per night (USD)VRBO
From $893 per night (USD)VRBO
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
100% private free standing house with private parking and entrance. No indoor common/shared areas. Quick walk thru woo ...
From $893 per night (USD)VRBO
From $1506 per night (USD)VRBO
General Williams Estate House Lenox/Stockbridge
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
The General Williams house is located 2 miles from Stockbridge Center and 5 miles from Lenox Center. Only 7 miles from ...
From $1506 per night (USD)VRBO
From $1516 per night (USD)VRBO
Chic Modern Farmhouse 1 Mile to Downtown Lenox
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Our Designer Farmhouse has been lovingly updated and impressively furnished with careful thought and no expense spared. ...
From $1516 per night (USD)VRBO
From $483 per night (USD)VRBO
Just You, the frozen lake, and 2 nearby ski areas! Perfect cozy winter getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy yet expansive 3 story home within 15 minutes of Lenox, Stockbridge, Tanglewood, Great Barrington, and Catamount and ...
From $483 per night (USD)VRBO
From $1180 per night (USD)VRBO
Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hour ...
From $1180 per night (USD)VRBO
From $1475 per night (USD)VRBO
Berkshires Retreat in Lenox - Main House
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 13
A private retreat in Berkshires set on 5 acres in prime location in Lenox - our all-season property offers secluded luxu ...
From $1475 per night (USD)VRBO
From $326 per night (USD)VRBO
Modern secluded home in wooded Setting
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This 2500 square foot home has an open floor plan downstairs with living-room kitchen and screen in porch at the back of ...
From $326 per night (USD)VRBO
From $410 per night (USD)VRBO
5 STAR CASUAL ELEGANCE for 5 STAR GUESTS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
HYDRANGEA HILL - [2027 WINTER SPECIAL RATES: January-April; 7+ nights; $185/night; 32+ nights - $140/ night.Scheduled p ...
From $410 per night (USD)VRBO
From $975 per night (USD)Expedia
Lake Buel Waterfront - 4 Bedrooms with private dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Idyllic Berkshire lakeside 4 bedroom cottage offering swimming, fishing, water sports and hiking. Waterfront location wi ...
From $975 per night (USD)Expedia
From $549 per night (USD)VRBO
Imagine Being Lakeside, Kayaks/Fishing/EV Charger
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: This two story lake home has all the room needed for you and your guests to experience the serenity of lake li ...
From $549 per night (USD)VRBO
From $646 per night (USD)VRBO
Family Friendly in Sheffield, private yet close to everything!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Your perfect country escape. Clean, spacious, light and airy home set in the middle of a meadow on 20 acres. Complete pr ...
From $646 per night (USD)VRBO
From $1193 per night (USD)VRBO
The Brookman: Renovated 6000 SF Estate On 40 Acres
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Summary: Previously owned by one of Hollywood’s most iconic actors, this 6,000 SF estate sits on 40 secluded acres with ...
From $1193 per night (USD)VRBO
From $867 per night (USD)VRBO
Stunning Summer Berkshires Retreat with Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy the summer at our newly remodeled 4 bedroom, 2 ½ bath home that is nestled among the farms just outside the town o ...
From $867 per night (USD)VRBO
From $786 per night (USD)VRBO
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Four Season Resort Living in the Private Beaver Pond Meadows Complex, near Jiminy Peak. This newly renovated fully furn ...
From $786 per night (USD)VRBO
From $429 per night (USD)Expedia
Peaceful Cabin close to Skiing and Hiking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
An authentic Berkshire Mountains experience awaits in Otis at this 3-bedroom, 2-bathroom vacation rental by Lindal Cedar ...
From $429 per night (USD)Expedia
From $293 per night (USD)VRBO
Private apartment in beautiful country barn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Berkshire living at its best! This lovely shaker barn on 2 open acres has three apartments. All are private. Rent one o ...
From $293 per night (USD)VRBO
From $197 per night (USD)Expedia
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled in the heart of the Berkshires, Jiminy Peak is the ultimate year-round escape. Whether you’re here for skiing, s ...
From $197 per night (USD)Expedia
From $543 per night (USD)VRBO
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Lake Ashmere! Our newly and completely renovated cottage features two bedrooms with comfy queen size beds, a ...
From $543 per night (USD)VRBO
From $680 per night (USD)Expedia
Lenox Grand Colonial with Pool by Evergreen Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Evergreen Home Vacation Rentals invites you to this spacious 4-bedroom home on a quiet cul-de-sac beneath October Mounta ...
From $680 per night (USD)Expedia
From $235 per night (USD)VRBO
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: You want to pop out of bed, walk out your door, and be right on the mountain - this is the place for you. This ...
From $235 per night (USD)VRBO
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Beautiful 4 Bedroom Townhouse in the Berkshires at Jiminy Peak Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Located slope side at Jiminy Peak mountain resort in Hancock, MA, this townhouse offers guests 4 bedrooms, 3 bathrooms, ...
Click For PricingVRBO
From $578 per night (USD)VRBO
Lakefront Retreat | Dock, Kayaks & Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to the peaceful shores of Long Bow Lake in the Berkshires. With a private dock, complimentary kayaks, a ...
From $578 per night (USD)VRBO
From $589 per night (USD)VRBO
New England Family Home with Hot Tub and Pool
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Family-Friendly New England style 5 bedroom home located in the Berkshire hills, remote setting minutes from Stockbridge ...
From $589 per night (USD)VRBO
From $307 per night (USD)VRBO
Fun Filmmaker's Bungalow wPool & Pro Screening Room
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Hollywood Bungalow in the Berkshires is a cool cozy rustic country bungalow featuring a screening room with incredible ...
From $307 per night (USD)VRBO
From $814 per night (USD)VRBO
Romantic and Secluded Berkshire's Gem
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Beautiful log cabin in the middle of private 5 acres of woods with all of the 21st-century amenities. We are 5 minutes a ...
From $814 per night (USD)VRBO
From $656 per night (USD)VRBO
Ski season is here!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Clean and bright, this updated unit is located in the heart of Jiminy and offers impeccable comfort and convenience. Pa ...
From $656 per night (USD)VRBO
From $1372 per night (USD)Expedia
Amore Estate - beautiful room with many places to explore and relax in.
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Fully renovated and decor updated in 2024! 8 acre property, shared with one carriage house not rented, with amazing vie ...
From $1372 per night (USD)Expedia
From $250 per night (USD)VRBO
Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This updated vintage 1900 home in North Adams is just a 10 minute walk to MASS MoCA, one of the country's largest contem ...
From $250 per night (USD)VRBO
From $411 per night (USD)VRBO
Private Berkshire Cabin on 27acres near Jiminy Peak.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Secluded mountain home surrounded by 27 acres yet convenient to major attractions including Jiminy Peak, Williamstown, L ...
From $411 per night (USD)VRBO
From $695 per night (USD)VRBO
Luxury Vacation Rental in the Berkshires!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Known for its thriving art institutions, outdoor activities, fall foliage, world-class museums, and renowned annual fest ...
From $695 per night (USD)VRBO
From $831 per night (USD)VRBO
Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Jiminy Peak Mountain Resort in the Berkshire Mountains! Our newly-renovated mountain retreat "The Lazy Bear" ...
From $831 per night (USD)VRBO
From $767 per night (USD)VRBO
Private, family-friendly 5-bedroom chalet for 10 with sauna, lake access, firepit, pizza oven, games, fast Wi-Fi, office and EV charger
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Trade busy days for crisp Berkshire mornings at a stylish chalet set on 3 private wooded acres near Benton Pond. Designe ...
From $767 per night (USD)VRBO
From $646 per night (USD)Expedia
Hot Tub, Chic Sexy Style booking Summer 26!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Aberdeen: Sparkling contemporary, sitting on 6+ acres, one-level living + privacy. 2 bedrooms, 2 full baths, fiber inter ...
From $646 per night (USD)Expedia
From $405 per night (USD)VRBO
Clean & Modern space with a mix of original warmth and charming renovation.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "The Hideaway On Main " in Stockbridge Center. Our recently renovated 2 bedroom unit offers a clean mix of ...
From $405 per night (USD)VRBO
From $5026 per night (USD)Expedia
Sunset Falls: A Berkshire Mountain Luxury Retreat
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to Sunset Falls, where luxury meets nature in this modern architecturally significant home on 167 private acres. ...
From $5026 per night (USD)Expedia
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Family Home With Big Yard On The Hill, Short Walk To Downtown And Lake Mansfield
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Spread out in this spacious family home. The first floor has an easy flow from room to room and includes a sunny eat-in ...
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From $313 per night (USD)VRBO
Cozy Cabin in the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our cozy cabin rental is the perfect escape for those seeking tranquility and natural beauty. Truly a four season cabin, ...
From $313 per night (USD)VRBO
From $555 per night (USD)VRBO
1840 Village Farmhouse with Modern Comforts
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Three bedrooms (2 queen; 1 single) plus den/guest room with queen-size pull-out couch. Comfortable living/dining area w ...
From $555 per night (USD)VRBO
From $663 per night (USD)VRBO
Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
For 2023, a massive gut reno has been completed, adding a 24ft wide sunroom overlooking the lake, 2 new bedrooms and a b ...
From $663 per night (USD)VRBO
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Escape to The Berkshires w/Pool by Evergreen Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Evergreen Home Vacation Rentals invites you to this stylish 4-bedroom home, filled with cheeky pop art and comfortable s ...
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Click For PricingExpedia
Rosecliff: Ultra-Lux Pool, Big Views, Green River, Sleeps 15
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 15
Rosecliff Amenities: Main House, Heated Pool with Pool house, Sleeps 13 in beds or 15 max. high speed WIFI internet and ...
Click For PricingExpedia
From $451 per night (USD)VRBO
Historic Stone Church in The Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Hinterland Hall was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Plac ...
From $451 per night (USD)VRBO
From $722 per night (USD)Expedia
Cape Home In the Beautiful Berkshires - Near Lenox & Bousquet
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Cozy Cape Cod home in the beautiful Berkshires in desired neighborhood. Close to Bousquet Ski Resort, Wild Acres, Tangle ...
From $722 per night (USD)Expedia
From $330 per night (USD)VRBO
Berkshire Mountainside Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Fabulous 4 season Berkshire condo rental has room for 9 guests. Ski from this condo to Bousquet Ski Area; enjoy spring r ...
From $330 per night (USD)VRBO
From $1004 per night (USD)Expedia
Luxury Redo: Hot Tub, Playroom, Fire-pit, Sleeps 12
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
This was the nicest vacation rental I've ever stayed at... Thank you, James May 2025 Creamery: Fully Renovated 5 Bedroom ...
From $1004 per night (USD)Expedia
From $647 per night (USD)VRBO
Lake Buel Waterfront: with Sparkling Views, Fire Pit and Kayaks!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Laurel Banks Waterfront: Amenities include 4 bedrooms, 2 full baths, all new mattresses and linens, high-speed fiber opt ...
From $647 per night (USD)VRBO
From $667 per night (USD)Expedia
The Penthouse, Downtown Lenox by Evergreen Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Evergreen Home Vacation Rentals invites you to experience luxury in the heart of Lenox. Just 10 minutes from Bousquet M ...
From $667 per night (USD)Expedia
From $330 per night (USD)VRBO
Walk to campus; open concept kitchen/living;nature trail at end of this quiet st
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
A private townhouse w/ 3 bedrooms (1 with Queen on main floor, 2 on second floor -King bed and twin bed the two upstairs ...
From $330 per night (USD)VRBO
From $298 per night (USD)VRBO
Berkshire Mountain Cottage: in the Heart of the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Berkshire Mountain Cottage is a warm and cozy hideaway located in the Berkshire hills. Its located between North Egremon ...
From $298 per night (USD)VRBO
From $443 per night (USD)VRBO
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Recently renovated home in the exclusive Lake Buel community very close to the Appalachian Trail, Butternut Ski Area, Do ...
From $443 per night (USD)VRBO
From $298 per night (USD)Expedia
Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
New listing ! Looking for a centrally located place to stay? This Berkshires home is 5 minutes from Bousquet Ski Resort ...
From $298 per night (USD)Expedia
From $668 per night (USD)VRBO
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Renovations just finished on this unique home, that originally dates to the 1700s. Great for families and big groups, wi ...
From $668 per night (USD)VRBO
From $591 per night (USD)Expedia
Outdoor Sauna, Hot tub, Fire Pit, Dogs Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax with the whole family or escape with your partner for a romantic getaway to Lovers Lane. Surrounded by trees and s ...
From $591 per night (USD)Expedia
From $742 per night (USD)VRBO
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
**Adventure Awaits in Every Season. Hike. Ski. Swim. Relax. Repeat**** Combining the beauty and solitude of our 5+ acres ...
From $742 per night (USD)VRBO
From $815 per night (USD)VRBO
Serene Berkshires Cabin w/ Deck & Fire Pit!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the charm, beauty, and fun of the Berkshires from this 4-bedroom, 3-bath Otis cabin. Featuring a peaceful woode ...
From $815 per night (USD)VRBO
From $343 per night (USD)VRBO
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay at the heart of it all. Walk to lifts, restaurants, shopping and amenities right from your door. It doesn’t get an ...
From $343 per night (USD)VRBO
From $247 per night (USD)Expedia
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This ski-in, ski-out loft is located right at the base of the mountain in the Thatcher Lodge in the heart of the village ...
From $247 per night (USD)Expedia
From $453 per night (USD)VRBO
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Dublinshire Farm is a giant shaker barn that has three private apartments. This newest listing, #3, is a charming 2 sto ...
From $453 per night (USD)VRBO
From $557 per night (USD)Expedia
A cozy home nestled in the Green Mountains of Vermont!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Our cozy home is great in all seasons! Comfortably furnished, it is a great place to read in front of the fire, set out ...
From $557 per night (USD)Expedia
From $301 per night (USD)VRBO
Lenox Lakeside Condo, Minutes to Tanglewood
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Five bedroom condo on 223 acre manicured estate in the heart of the Berkshires. Laurel Lake views from most rooms and us ...
From $301 per night (USD)VRBO
From $381 per night (USD)Expedia
Quiet Cabin On Over 12 Acres Of Woods!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: This home features both modern finishes & New England charm. Large open great room, chef's kitchen & brick fir ...
From $381 per night (USD)Expedia
From $490 per night (USD)VRBO
Family Friendly Raised Cape in the Center of Lenox Village
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This renovated raised cape is in the center of historic Lenox, MA. 3 large bedrooms. 2 full bathrooms. Master bedroom ha ...
From $490 per night (USD)VRBO
From $183 per night (USD)Expedia
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Welcome to modern country comfort. This unique Suite lies right on Jiminy Peak Mountain within the Country Inn ...
From $183 per night (USD)Expedia