Berkshire Area Rentals
From $327 per night (USD)VRBO
Cozy Winter Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our darling cottage is a lovely, quiet retreat just minutes from some of the most iconic spots in the Berkshires! The ...
From $327 per night (USD)VRBO
From $188 per night (USD)Expedia
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: You want to pop out of bed, walk down hall, and be right on the mountain This 1BR 1 BA off lobby Unit has som ...
From $188 per night (USD)Expedia
From $331 per night (USD)VRBO
A-Frame Cabin w/ Furnished Deck in Becket!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Built in 1974 | Private Acreage & Scenic Surroundings | Fireside Relaxation | EV Charger Embrace a slower pace of life ...
From $331 per night (USD)VRBO
From $200 per night (USD)VRBO
Great Place - 2 BD - Kitchen and Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick ...
From $200 per night (USD)VRBO
From $874 per night (USD)VRBO
Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Discover a unique getaway in the heart of Stockbridge, Massachusetts, at the historic rectory of St. Joseph's Church. Pe ...
From $874 per night (USD)VRBO
From $910 per night (USD)VRBO
2 Bedroom Deluxe Condo, Sleeps 8, Jiminy Peak Mountain Skiing, at Bentley Brook!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This spacious two-bedroom resort suite measures approximately 843 to 953 square feet. You will enjoy a king bed in the m ...
From $910 per night (USD)VRBO
From $241 per night (USD)VRBO
Mountainside Condo Ski In Ski Out
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Recently Renovated!! Nestled in the Berkshires, a getaway to Jiminy Peak offers everything you need, so close to home. J ...
From $241 per night (USD)VRBO
From $486 per night (USD)Expedia
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the breathtaking views of Mt. Everett from one of the oldest homes in the Berkshires. Our meticulously mainta ...
From $486 per night (USD)Expedia
From $551 per night (USD)VRBO
Guesthouse Cabin vacation rentals in Berkshire County
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Undermountain Lodge offers an escape to a serene cabin, nestled between pristine natural spring lakes with panoramic mou ...
From $551 per night (USD)VRBO
From $719 per night (USD)VRBO
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Family or couples getaway! 3 bedrooms plus library, Sleeps 6-8 A beautiful 3050 Sq. Ft., 2-Story Colonial and attached ...
From $719 per night (USD)VRBO
From $237 per night (USD)VRBO
Come to the Berkshires for outdoor enthusiast, or a relaxing couple retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come and spend a weekend relaxing by a fire or exploring the many restaurants and outdoor activities from this unique an ...
From $237 per night (USD)VRBO
From $352 per night (USD)Expedia
Luxe Log Cabin Minutes From Skiing, Hiking, & More
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Escape to the Berkshires in our newly-restored, cozy-luxe cabin, complete with fireplace, fully-stocked kitchen, high-sp ...
From $352 per night (USD)Expedia
From $619 per night (USD)VRBO
Butternut Ski Retreat - Fireplace, Views and close to town!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This contemporary, light-filled 3BR, 2.5BA home is less than a mile from Lake Mansfield and downtown Great Barrington, w ...
From $619 per night (USD)VRBO
From $580 per night (USD)Expedia
Family Lodge at Jiminy Peak - Pools & Adventure
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
<p>Escape to the Berkshires at Left Bank Lodge! Spacious 4BR/3BA townhome at Jiminy Peak sleeps 13 with 2 living rooms, ...
From $580 per night (USD)Expedia
From $566 per night (USD)VRBO
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Enjoy the last days before the Resort closes for good! Welcome to Wyndham Bentley Brook, your gateway to the ultimate s ...
From $566 per night (USD)VRBO
From $622 per night (USD)Expedia
Brick Patio + Firepit + Hammock | Clawfoot Tub + Cottage Charm | Cordelia
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Cordelia is a cottage in the best sense of the word: chic where it counts, unfussy everywhere else, and built around out ...
From $622 per night (USD)Expedia
From $588 per night (USD)VRBO
Cozy Lakeside Cottage Oasis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to our charming lakeside cottage on Brewer Pond, the tranquil extension of Lake Garfield! If you're seeking a se ...
From $588 per night (USD)VRBO
From $507 per night (USD)Expedia
Perfect Family Gateway Spot for the Berkshires, Jiminy Peak Skiing, MASS MoCA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Discover the Ultimate Berkshires Retreat: The Berkshire Apple House 🌟 Luxurious Comfort in the Heart of Berkshires N ...
From $507 per night (USD)Expedia
From $309 per night (USD)VRBO
The Blue Elm - A Historic Berkshire Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to The Blue Elm - a cozy and historic Berkshire getaway located in Ashley Falls, MA. Set on 3.5 tranquil acres, ...
From $309 per night (USD)VRBO
From $186 per night (USD)Expedia
Remodeled Unit #2, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in history and nature, The Historic Kellogg House, built in 1739, is the third oldest house in the Berkshires. R ...
From $186 per night (USD)Expedia
From $658 per night (USD)VRBO
Sunsets On Blue Hill, Newly Renovated Farmhouse
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: Welcome to Great Barrington! The heartbeat of the Berkshires! This newly remodeled home is conveniently loc ...
From $658 per night (USD)VRBO
From $563 per night (USD)Expedia
Great Barrington Lakeside Getaway w/ Kayak & Grill
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy stunning water views and lakeside fun at this 4-bedroom + den, 4-bath vacation rental in the Berkshires. A mixture ...
From $563 per night (USD)Expedia
From $303 per night (USD)VRBO
2-Bdr Apt In Town, By the Water
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
★ New to Williamstown? Explore our interactive guidebook. A flight of steps takes you to this stunning 2BDR on the 2nd ...
From $303 per night (USD)VRBO
From $280 per night (USD)Expedia
Downtown | Waterfront | Walk to Shops
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
★ New to Williamstown? Explore our interactive guidebook. One bedroom with all the bells and whistles! Meticulously upg ...
From $280 per night (USD)Expedia
From $574 per night (USD)VRBO
Refined Berkshires Haven. Between Stockbridge & Lenox. Nature, Arts & Wellness
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This stylish Berkshires retreat is ideally located between downtown Stockbridge and Lenox, just minutes from Great Barri ...
From $574 per night (USD)VRBO
From $798 per night (USD)VRBO
Ray of Sunshine Berkshire Home on Pontoosuc Lake
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Brand new construction directly on Lake Pontoosuc. This home sleeps 14 guests. There is a brand new chef’s kitchen! Th ...
From $798 per night (USD)VRBO
From $371 per night (USD)VRBO
Lakeshore cabin with beach and dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
A classic Berkshire cabin nestled under maple trees, on the shore of the Stockbridge Bowl cove, next to a waterfall. Ser ...
From $371 per night (USD)VRBO
From $1094 per night (USD)VRBO
Luxury Retreat Minutes from Great Barrington & Ski Slopes
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Set on 10 private acres in the quiet town of Alford, less than 10 minutes from downtown Great Barrington, this beautiful ...
From $1094 per night (USD)VRBO
From $319 per night (USD)VRBO
Sweet Cozy Victorian in Housatonic. Close to everything.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newl ...
From $319 per night (USD)VRBO
From $846 per night (USD)Expedia
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Located near Lenox, Stockbridge, and Lee, this private and peaceful country house with modern amenities offers a relaxin ...
From $846 per night (USD)Expedia
From $978 per night (USD)VRBO
Mountain Blossom Retreat by Evergreen Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Evergreen Home Vacation Rentals invites you to this luxury haven at the base of Mount Greylock. Nestled on 60 private ac ...
From $978 per night (USD)VRBO
From $1184 per night (USD)VRBO
Berkshire 6BR Estate • Pool, Hot Tub, Game Room
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 14
Welcome to your own Berkshire's retreat! Our 6 bedroom estate on 4 acres is perfect for large families and groups to gat ...
From $1184 per night (USD)VRBO
From $561 per night (USD)VRBO
Autumn in Stockbridge
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
One of TWO lovely dwellings for rent on nearly four private acres. See VRBO 3529604 to learn more about our Charming Ber ...
From $561 per night (USD)VRBO
From $378 per night (USD)Expedia
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A perfect stay in the Berkshires! Just 1.5 miles from downtown Great Barrington and 1 mile from Butternut Ski Area, our ...
From $378 per night (USD)Expedia
From $735 per night (USD)VRBO
LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Enjoy this very private, super comfortable, 1925 lake cottage, waterfront boathouse and dock for an entire Berkshire Sum ...
From $735 per night (USD)VRBO
From $432 per night (USD)Expedia
Waterfront Cottage 10 Min From Great Barrington
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A couple's getaway for the books awaits you at this Lake Buel vacation rental. Just 6 miles from Great Barrington's shop ...
From $432 per night (USD)Expedia
From $368 per night (USD)VRBO
house with view in the berkshires
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the charm of this newly renovated home with a wrap-around deck with seasonal vistas of a lake and mountains. ...
From $368 per night (USD)VRBO
From $444 per night (USD)VRBO
Light-Filled Family Home in the Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Light-filled modern 4 bedroom, 3.5 bath home in the Berkshires. This lovely two story home features a master bedroom on ...
From $444 per night (USD)VRBO
From $256 per night (USD)VRBO
Gateway to the Berkshires - Renovated downtown apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Completely renovated downtown second floor apartment with open floor plan, located in historical downtown Lee. This apar ...
From $256 per night (USD)VRBO
From $729 per night (USD)VRBO
Luxury Cabin with Views & Deck besides Kennedy Park, Walk to Lenox.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Elegant, light-filled cabin blending modern comfort with rustic charm, nestled beside Kennedy Park. Enjoy mesmerizing ...
From $729 per night (USD)VRBO
From $393 per night (USD)VRBO
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
720 Sq. Ft, 2 Bed, 1 Bath cottage with HOT TUB amongst the forest located in a private, dirt road, lake community with n ...
From $393 per night (USD)VRBO
From $2395 per night (USD)VRBO
Spacious 4 bedroom, big pool & outdoor space. Close for local summer activities!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Less than 2 miles from Williams College, this a great homebase for the upcoming Williams events or other summer events i ...
From $2395 per night (USD)VRBO
From $461 per night (USD)VRBO
Berkshires Lakefront Gem
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is the perfect getaway for people who want to unwind from the grind of everyday life. This house is lakefront. A ...
From $461 per night (USD)VRBO
From $368 per night (USD)VRBO
Luxury on the River near Tanglewood w/220 EV Charge
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax with the entire family in this beautiful new home built on the Farmington River. Enjoy luxurious, natural open spa ...
From $368 per night (USD)VRBO
From $311 per night (USD)VRBO
Berkshires' best! Tanglewood, Jacob's Pillow and 400 feet from a pristine lake
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This newly renovated house in the woods on a private road in Lee is an ideal summer or fall retreat. Our little communit ...
From $311 per night (USD)VRBO
From $610 per night (USD)Expedia
Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to Tranquility Glade, a newly renovated modern chalet set on 5.5 private forested acres in West Stockbridge, Mass ...
From $610 per night (USD)Expedia
From $646 per night (USD)VRBO
Lake Haven with new dock and amazing views of Lake Garfield
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax with the whole family at this peaceful lakeside home. Enjoy the lake-facing deck for dining and drinks. Swim/boat/ ...
From $646 per night (USD)VRBO
From $226 per night (USD)VRBO
Two 2BR Villas l From Sauna to Sports Courts – Comfort & Fun for Everyone
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Escape to the Berkshires! Experience hiking, boating, and skiing at our doorstep. Nearby, enjoy the Norman Rockwell Muse ...
From $226 per night (USD)VRBO
From $403 per night (USD)VRBO
Jiminy Peak Resort Townhome, Sleeps 10, Pool, Hot Tubs, Sauna & Deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Stay directly on the grounds of Jiminy Peak Mountain Resort in a spacious four-level townhome designed for families and ...
From $403 per night (USD)VRBO
From $110 per night (USD)VRBO
Resort Stay with Arcade, Heated Pool, Sports Courts & Family Perks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to the Berkshires! Experience hiking, boating, and skiing at our doorstep. Nearby, enjoy the Norman Rockwell Muse ...
From $110 per night (USD)VRBO
From $550 per night (USD)VRBO
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Conveniently located near a lake, off of Route 7 on the way to attractions in both North Berkshire County and Southern B ...
From $550 per night (USD)VRBO
From $558 per night (USD)Expedia
Urban Peak Escape, Lenox, MA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover Urban Peak Escapes in Lenox, MA—a charming New England town in the Berkshires. Just 1 mile from Tanglewood and ...
From $558 per night (USD)Expedia
From $244 per night (USD)VRBO
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dreaming of waking up, heading downstairs, and being right on the mountain? This is the place for you. Conveniently loca ...
From $244 per night (USD)VRBO
From $608 per night (USD)Expedia
Perfect Nature Haven In Great Barrington
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to your home for the week in Great Barrington—a spacious, nature-surrounded retreat. Just a 2-minute d ...
From $608 per night (USD)Expedia
From $197 per night (USD)VRBO
Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
After a day of mountain adventures, our Resort in the Berkshires is the perfect New England-y place to unwind and kick o ...
From $197 per night (USD)VRBO
From $309 per night (USD)Expedia
Becket Home w/ 3-Season Porch: Walk to Lake Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Unwind and embrace nature at this charming Becket vacation rental! With views of Lake Robinhood and a screened porch for ...
From $309 per night (USD)Expedia
From $393 per night (USD)VRBO
Berkshire Holiday Home - A+ Amenities& Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Book your next vacation at our special Berkshire Holiday home set on several acres in the beautiful Berkshire Mountains ...
From $393 per night (USD)VRBO
From $610 per night (USD)Expedia
Berkshires Lakefront Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Catch your breath…and let nature take it away again... Private and serene, our beautiful lakefront home is your idylli ...
From $610 per night (USD)Expedia
From $216 per night (USD)VRBO
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Historic home Nestled on a quiet street in downdown Great Barrington, just steps from the River Walk path, this enchanti ...
From $216 per night (USD)VRBO
From $323 per night (USD)Expedia
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Just bring your clothes and food! Everything else is here. Everything to cook with clean, shower, extra linens and blank ...
From $323 per night (USD)Expedia
From $626 per night (USD)VRBO
Lakefront Home on Pontoosuc Lake, the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stunning Lakehouse: Lakefront property & house on 1-acre on Pontsoosuc Lake in western MA, 2600 sq.ft., 3 bedrooms / 2 ...
From $626 per night (USD)VRBO
From $615 per night (USD)Expedia
Beautiful Berkshire family home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
This is a beautiful 5 bedroom Berkshire, post and beam private house nestled in the woods just off the Appalachian trail ...
From $615 per night (USD)Expedia
From $481 per night (USD)VRBO
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled on picturesque grounds, this modern and updated 3-bedroom home offers the perfect blend of comfort and luxury. E ...
From $481 per night (USD)VRBO
From $497 per night (USD)VRBO
Charming 3-bedroom Salt Box house in quaint Williamstown Mass with WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 2
WILLIAMSTOWN MASSACHUSETTS RENTAL 18 THORNLIEBANK ROAD FURNISHED 3 BEDROOM 2 CAR GARAGE ...
From $497 per night (USD)VRBO
From $1306 per night (USD)VRBO
Serene 5-BR Retreat 9-Min to Catamount
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Gather your friends and family at this a luxurious 5-BR retreat. Nestled in the serene woodlands of the Berksh ...
From $1306 per night (USD)VRBO
From $407 per night (USD)Expedia
Cozy Condo Near MASS MoCA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Your Modern Bohemian Retreat in North Adams Experience a blend of contemporary comfort and bohemian charm in ...
From $407 per night (USD)Expedia
From $721 per night (USD)VRBO
Steepletop - Nature Lovers Paradise with Rec Room
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to Steepletop Lodge, a beautiful 4 bed/ 2 bath modern retreat with endless opportunities to unplug and ...
From $721 per night (USD)VRBO
From $541 per night (USD)VRBO
Meadow Top Cottage: Countryside Cottage on 72 Acres
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Meadow Top Cottage is charming and cozy 3-bed, 2-bath cottage in the quiet hamlet of Mill River, MA. The 72-ac ...
From $541 per night (USD)VRBO
From $468 per night (USD)VRBO
Solomon Ely Homestead - Charming Pittsfield Stay
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Enjoy your stay at this 1847 New England farmhouse located just steps from downtown Pittsfield. Make yourself at home wi ...
From $468 per night (USD)VRBO
Click For PricingExpedia
Cozy Home in Lenox
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Enjoy a stylish experience at this cozy newly renovated two-bedroom mobile home in the Berkshires of Lenox, Massachusett ...
Click For PricingExpedia
From $861 per night (USD)VRBO
The Race Mountain House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
High on the slopes of Race Mountain, this spacious 4-bedroom villa offers sweeping east-facing views. In the early hours ...
From $861 per night (USD)VRBO
From $478 per night (USD)VRBO
Serene rustic cabin in the Berkshires!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Need a break from city life? Escape to our enchanting private cabin nestled in the woods, where romance and seclusion aw ...
From $478 per night (USD)VRBO
From $546 per night (USD)VRBO
Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to this superb fully equipped house on our 220 acre lake estate. With 4 bedrooms including 1 queen bed, 3 twin be ...
From $546 per night (USD)VRBO
From $504 per night (USD)Expedia
Sun Filled Lenox Retreat - Minutes to Tanglewood!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy all the Berkshires has to offer from this charming 3BR/2BA home base for up to 10 people just 5 minutes from downt ...
From $504 per night (USD)Expedia
From $437 per night (USD)VRBO
Stockbridge house 17 minutes from Tanglewood. Four bedroom, three bathroom.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Recently built 4-bedroom, 3-bathroom Cape Cod style house set apart from neighbors. Very close to Norman Rockwell museu ...
From $437 per night (USD)VRBO
From $552 per night (USD)Expedia
Lake Views & Dock Access - Pittsfield Cottage!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Waterfront Yard | Furnished Sunroom | Boat Dock | Beach Gear Provided Nestled in the serene town of Pittsfield, 'Pontoo ...
From $552 per night (USD)Expedia
From $381 per night (USD)VRBO
Zen Riverfront studio w/ Spa steam shower, wood stove, SKI Catamount /Butternut
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in Great Barrington, this marvelous, newly renovated, sunny studio features a well equipped kitchenette, a c ...
From $381 per night (USD)VRBO
From $2213 per night (USD)VRBO
Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Moose Lodge – A 7,500 Sq. Ft. Berkshires Luxury Retreat Experience the pinnacle of comfort and entertainment ...
From $2213 per night (USD)VRBO
From $570 per night (USD)VRBO
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Located in Lanesborough, guests love this Cozy Cottage aka “Polly’s Place” for its warmth, central location and accessib ...
From $570 per night (USD)VRBO
From $456 per night (USD)VRBO
Cheever Hollow Farm an essential retreat central to Lenox and the Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to Cheeverhollowfarm in picturesque Richmond/Lenox. Please Contact me for specific details or requests. We are ...
From $456 per night (USD)VRBO
From $596 per night (USD)VRBO
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
<p>Welcome to the Mt. Williams Retreat—a centrally located guesthouse just two blocks from Williams College. Designed fo ...
From $596 per night (USD)VRBO
From $551 per night (USD)VRBO
NEW! Berkshire Bliss. Cheery & comfortable private home in Williamstown Center
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
NEW to VRBO! Absolutely adorable private house in Williamstown just 3 minutes from Spring St,, Clark Art and Williams Co ...
From $551 per night (USD)VRBO
From $183 per night (USD)VRBO
Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- Home Away From Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The most unique Suite in the Berkshires - This gorgeous redone Hotel=like Suite will make your summer retreat ...
From $183 per night (USD)VRBO
From $260 per night (USD)Expedia
Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This private Luxurious Guest house will Amaze you, with full kitchen, living area and large bedroom with Luxurious Queen ...
From $260 per night (USD)Expedia
From $495 per night (USD)VRBO
The Hideaway: Berkshire Home - Village of Egremont
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our home in the village of Egremont (part of Great Barrington). Both the house and property are open and inv ...
From $495 per night (USD)VRBO
From $801 per night (USD)VRBO
The Maple House - Modern Retreat Near Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: You will enjoy your stay at The Maple House, a beautifully restored mid-century modern retreat in the Berkshire ...
From $801 per night (USD)VRBO
From $6261 per night (USD)VRBO
Winthrop Estate – An Elegant Home
- Bedrooms:
- 10
- Bathrooms:
- 12
- Sleeps:
- 24
Summary: I’m Jamie, the proud steward of the timeless, beautiful Winthrop Estate, a restored 1920s mansion that blends ...
From $6261 per night (USD)VRBO
From $1356 per night (USD)Expedia
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Stunning 5BR/5.5BA 4,500 sq ft home with soaring 25-ft ceilings, modern finishes, pearched in the trees with sparkeling ...
From $1356 per night (USD)Expedia
From $1633 per night (USD)VRBO
Spacious Luxury Berkshire's Estate on 21 acres
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
The Fox Hollow Estate is a private 1940s estate home, renovated to modern-day luxury, located in gorgeous Berkshire Coun ...
From $1633 per night (USD)VRBO
From $323 per night (USD)Expedia
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: You want to bring your whole family to Jiminy and be in ONE CONDO, with gorgeous views, a deck, BBQ, Backyard, ...
From $323 per night (USD)Expedia
From $249 per night (USD)VRBO
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Experience the Magic of the Berkshires in this charming 1BR 1 BA Suite which Sleeps 4 comfortably with its King ...
From $249 per night (USD)VRBO
From $245 per night (USD)Expedia
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The most fun Suite in the Berkshires - This gorgeous Gamers Suite will bring Families together Like No Other! N ...
From $245 per night (USD)Expedia
From $242 per night (USD)VRBO
A First floor 2-bedroom apartment in North Adams. Plenty of off-street parking.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in North Adams, this delightful first floor apartment boasts 2 cozy bedrooms - one with a queen bed and the othe ...
From $242 per night (USD)VRBO
From $533 per night (USD)Expedia
Bidwell Landing | Lakefront • Spacious
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy this spacious 4 bed, 4 bath home nestled on Lake Garfield in the beautiful Berkshires. Well-curated, clean, and pe ...
From $533 per night (USD)Expedia
From $528 per night (USD)VRBO
Pet Friendly Oasis on 5 Private Acres, 10 min to Tanglewood
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Escape to this peaceful retreat on 5 private acres. Large picture windows envelope you in the gorgeous surroundings, and ...
From $528 per night (USD)VRBO
From $606 per night (USD)Expedia
Available February 17-21 2025. Sleep 8 - 2-bed apt on Jiminy Peak. Ski in/out!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Available February 17-21 - President’s week 2025! Condo Resort at Jiminy Peak Ski Mountain's Base Enjoy ski retreat at ...
From $606 per night (USD)Expedia
From $245 per night (USD)VRBO
Charming Lakeview Cottage in Heart of the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Relax in your island cottage overlooking beautiful Onota Lake in the heart of the Berkshires. Take in 180 degree pristin ...
From $245 per night (USD)VRBO
From $1047 per night (USD)Expedia
Contemporary Berkshire Home with Views of Taconic Golf Course
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Discover peace and beauty at this one of a kind Berkshire home designed by Maya Lin (Vietnam Memorial Wall Architect). ...
From $1047 per night (USD)Expedia
From $125 per night (USD)VRBO
family friendly retreat condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to this adorable apartment in Pittsfield. This cozy space features 1 bedroom with a comfortable queen bed, a ful ...
From $125 per night (USD)VRBO
From $472 per night (USD)Expedia
Secluded 3-BR Cabin Near Jacob's Pillow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to a peaceful 3-bedroom cabin surrounded by the forests of the Berkshires. Designed for families and fr ...
From $472 per night (USD)Expedia