Berkshire Area Rentals
From $1117 per night (USD)VRBO
Gracious Williamstown Home with Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
This lovely home is located less than two miles from the Williams campus and has been fully updated, maintaining the bea ...
From $1117 per night (USD)VRBO
From $449 per night (USD)Expedia
Cabin w\/ 3 Acres, Tennis Courts: By 4 Ski Mtns
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 10
Take a trip to this 4-bed, 3-bath vacation rental in Sandisfield, MA! Hidden between the Sandisfield and Otis State Fore ...
From $449 per night (USD)Expedia
From $221 per night (USD)VRBO
Rustic Berkshires Cottage at Lake Buel w\/ Kayaks!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Bring your loved one or best friend along on a Berkshires getaway to this rustic 1-bedroom, 1-bath vacation rental in Ne ...
From $221 per night (USD)VRBO
From $273 per night (USD)Expedia
'The Mill River Cabin’ w\/ Fireplace & River View!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 5
Reconnect with Mother Nature at this 2-bedroom, 1-bath cabin loaded with character! Minutes from the Historic Mill River ...
From $273 per night (USD)Expedia
From $185 per night (USD)VRBO
The Perfect Escape; Log Cabin situated on 40 Secluded Acres of Wilderness
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
https://www.partridgehillberkshires.com/ Under 3 hours from New York City and Boston, find yourself immersed in a four ...
From $185 per night (USD)VRBO
From $220 per night (USD)Expedia
Berkshire Village Carriage House - Super Private!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Private, unique getaway in the center of the Berkshires. We're a 3 minute walk to the Ashuwillticock rail trail. Situat ...
From $220 per night (USD)Expedia
From $432 per night (USD)VRBO
Log style home 4 miles to Catamount with fitness room
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
In the summer spend time on the large screened porch and decks. Great room has sliding doors leading to deck facing eas ...
From $432 per night (USD)VRBO
From $234 per night (USD)Expedia
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up ...
From $234 per night (USD)Expedia
From $593 per night (USD)VRBO
The best of both worlds, Country and Culture
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
5 bed rooms, 3 full baths, large kitchen with a prep pantry. Master bedroom on the 1st floor, another master on the 2nd ...
From $593 per night (USD)VRBO
From $388 per night (USD)Expedia
4 BR home w\/ beautiful gardens on pond in Berkshires. Walking distance to town.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This house is close to Everything!! Tanglewood (3 miles), Kripalu (3 miles), theaters, Jacob's Pillow, Lee Outlets, etc ...
From $388 per night (USD)Expedia
From $303 per night (USD)VRBO
3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Spacious living/kitchen area, located on a quiet street and central location walkable to campus and restaurants, museums ...
From $303 per night (USD)VRBO
From $274 per night (USD)Expedia
Stockbridge Home: Walk to Town Beach!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Escape to a lake retreat with this 3-bedroom, 1-bathroom vacation rental home in Stockbridge. Stockbridge Bowl's grassy ...
From $274 per night (USD)Expedia
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Home in The Berkshires - Becket
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
New house in Becket. The house is located in the heart of Berkshire where all the cultural activities are around: Jacob' ...
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From $702 per night (USD)Expedia
Tranquil Lake House Getaway on Onota Lake
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Beautiful lake front house on 1.7 wooded acres on a very quiet end of Onota Lake. A long driveway takes you to this lo ...
From $702 per night (USD)Expedia
From $216 per night (USD)VRBO
Beautifully decorated & immaculate log chalet on 3 acres, winter views.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private and secluded log cabin chalet is situated on three picturesque acres overlooking tall pines and forests with he ...
From $216 per night (USD)VRBO
From $337 per night (USD)Expedia
Tranquil 3 BR Stockbridge House w\/ Private Deck!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house! Boasting a private dec ...
From $337 per night (USD)Expedia
From $203 per night (USD)VRBO
Monthly\/Yearly, All Season Vacation Rental, Minutes from Jimney Peak, MA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fully funished charming openspace house with kitchen dining and living areas, modern wood stove , contemporary master b ...
From $203 per night (USD)VRBO
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The Freeman - Newly Renovated 14K SF Estate on 40 Acres
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 30
The Freeman Berkshires sits on 40 acres of manicured landscape with a tennis court, a four-acre vineyard, a myriad of am ...
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From $412 per night (USD)VRBO
The Lenox House. In the center of Lenox and the Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Beautifully restored and renovated downtown Lenox House. 4 Bedrooms and common area equipped with mini split heating / ...
From $412 per night (USD)VRBO
From $764 per night (USD)Expedia
Gorgeous Sheffield Home in Heart of Berkshires
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Our home is a beautiful mountain-style home (exposed beams, wood floors, all new appliances) on a quiet rural road with ...
From $764 per night (USD)Expedia
From $546 per night (USD)VRBO
Luxurious, modernist barn in peaceful northwestern Connecticut - private swim!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
OPEN for Memorial Day! Our Connecticut retreat is equidistant from NYC and Boston and sits on 23 wooded acres with a ser ...
From $546 per night (USD)VRBO
From $348 per night (USD)Expedia
Beautiful Period Home in the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Situated on 26 acres in the heart of the Berkshires in the small town of South Egremont, MA, this early 19th c. house co ...
From $348 per night (USD)Expedia
From $201 per night (USD)VRBO
2 bedroom Riverhouse in the Heart of the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located between the villages of Stockbridge, Housatonic and Great Barrington. Most unique Riverhouse property located on ...
From $201 per night (USD)VRBO
From $281 per night (USD)Expedia
Simply Elegant Log Home Only 3 Minutes From Butternut! Recently renovated!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
Comfortably sleeping 8 to 10 people, this sunny log cabin has a fireplace on each of its three levels, making it especia ...
From $281 per night (USD)Expedia
From $337 per night (USD)VRBO
Serene Berkshire Artist's House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful, comfortable artist's house, that is tastefully furnished. Located on a very quiet 5 acre property abutting Mt ...
From $337 per night (USD)VRBO
From $503 per night (USD)Expedia
Great Barrington Walkable to Lake and Town!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
Summary: Easy & comfortable living on “The Hill” of Great Barrington. Our welcoming space has lots of personal touches, ...
From $503 per night (USD)Expedia
From $785 per night (USD)VRBO
Great Barrington, Cabin Sleeps 14, Walk To Town
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: You and your family cannot beat this PRIME location in downtown Great Barrington while still feeling remote and ...
From $785 per night (USD)VRBO
From $470 per night (USD)Expedia
Home in the Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
We are renting our 4 bedroom vacation house on 3 acres in the Berkshires for the summer/fall/winter. It has 2 master sui ...
From $470 per night (USD)Expedia
From $630 per night (USD)VRBO
Renovated Downtown Great Barrington House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Newly renovated three bedroom “on the hill” in Great Barrington awaits your next family stay. Short walk to dow ...
From $630 per night (USD)VRBO
From $1097 per night (USD)Expedia
ONTARA....
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
ONTARA, Place of the New Light...in the Berkshires...on the mountainside, with the back of the property on the New York ...
From $1097 per night (USD)Expedia
From $414 per night (USD)VRBO
19th c. Barn in the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Mason Hill Farm is a celebration of everything we love about the Berkshires. Mountain views, a rushing swimmable brook, ...
From $414 per night (USD)VRBO
From $339 per night (USD)Expedia
Home in Great Barrington
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Central and Private!! Just steps away from historic downtown Great Barrington and East Mountain Hiking trails. Enjoy su ...
From $339 per night (USD)Expedia
From $393 per night (USD)VRBO
Huge Beautiful House-fits 2 families-16 Acres -Low rates- 2 min from Jiminy Peak
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
2 MIN TO JIMINY PEAK - right down the road! Close to Lenox and Williamstown! Reduced rates. Great for 2 families (max 8 ...
From $393 per night (USD)VRBO
From $523 per night (USD)Expedia
5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
NOTE: Our street name has changed to Woodland Hill (from Squaw Peak). Same house, same house number - different street ...
From $523 per night (USD)Expedia
From $346 per night (USD)VRBO
Beautiful Waterfront home with deep water dock on Onota Lake
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Our 3 bedroom, 2 bath home has a huge 3 season sun room on the second floor with an even bigger covered deck below. The ...
From $346 per night (USD)VRBO
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Stockbridge Bowl Lake Community
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Charming new construction home located in neighborhood community that has a private beach on the Stockbridge Bowl. Just ...
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From $297 per night (USD)VRBO
Spacious Victorian duplex near MASSMoCA, MCLA (19)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This gorgeous late 19th century Victorian duplex recently under went a complete renovation. Situated on a lovely quiet s ...
From $297 per night (USD)VRBO
From $619 per night (USD)Expedia
Restful pastoral, kids-friendly home w\/ gardens, views, swimming pool, sauna
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Contemporary dwelling in a beautiful pastoral setting. Viking stove, wood-burning fireplace, gunite heated saltwater poo ...
From $619 per night (USD)Expedia
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Mountain View Retreat w\/ Hot Tub by Evergreen Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
12 MINUTES FROM BOUSQUET SKI AREA Exceptional VIEWS!! Take in the sunrise sipping coffee on the front porch & the sunset ...
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From $197 per night (USD)Expedia
Cozy and quaint country cottage, walk to downtown Williamstown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to charming duplex in-law home in a family friendly neighborhood. This private and nicely decorated apartment, w ...
From $197 per night (USD)Expedia
From $589 per night (USD)VRBO
Elegant & private light-filled 1 level, available Sept. 1 - Oct. 31- disc. 20%
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
With soaring cathedral ceilings and light filled tranquility, off a quiet cul de sac road, this is the perfect place for ...
From $589 per night (USD)VRBO
From $369 per night (USD)Expedia
Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Booking for the 2022 Fall Season. For more photos and information go to our website at www.lenoxmarental.com. Enjoy the ...
From $369 per night (USD)Expedia
From $909 per night (USD)VRBO
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Our 6BR home is super comfortable, designed for multiple families to share (max 14 guests), up to date, and just minutes ...
From $909 per night (USD)VRBO
From $535 per night (USD)Expedia
In the heart of the Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This meticulously cared for home is just ideal for year-round or vacation living. Enjoy the private screen porch on sum ...
From $535 per night (USD)Expedia
From $291 per night (USD)VRBO
Becket Contemporary Cottage in the Woods Overlooking a Private Spring Fed Pond
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our Tree House in the Berkshires has a view of the forest out every window. Our home overlooks a spring fed pond and is ...
From $291 per night (USD)VRBO
From $1034 per night (USD)Expedia
Beautiful Berkshire Farm House on 160+ Acres
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
This is a unique property located on more than 1000 feet of the Green River. Over a hundred and sixty acres of beautiful ...
From $1034 per night (USD)Expedia
From $137 per night (USD)VRBO
Hancock, MA: Studio w\/Valley Views at All-Seasons Resort: Skiing, Hiking & More!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Complete your Berkshires retreat with a stay in the spacious Studios, perfect for romantic couples and small families. S ...
From $137 per night (USD)VRBO
From $574 per night (USD)Expedia
Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Tastefully appointed farmhouse getaway set high in the picturesque Tyringham Valley with access to a tennis/pickle ball ...
From $574 per night (USD)Expedia
From $675 per night (USD)VRBO
Renovated Lakefront House w\/ Dock: Pets Welcome!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
With 150 feet of lakefront property on Lake Buel - a 192-acre mountain lake - this 4-bedroom, 2.5-bath vacation rental i ...
From $675 per night (USD)VRBO
From $298 per night (USD)Expedia
Berkshire Lake access
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Our beautiful offshore lake house is walking distance to a private HOA beach. Bring friends or family to our four bedro ...
From $298 per night (USD)Expedia
From $226 per night (USD)VRBO
COZY LOFT w\/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
The LOFT is a unique private large 690 s.f. modern cabin like structure with great forest and garden views and access ...
From $226 per night (USD)VRBO
From $758 per night (USD)Expedia
Stunning Lakefront Berkshire Rental, Lake Garfield: private dock, boats, more
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, paddleboard, sunbat ...
From $758 per night (USD)Expedia
From $268 per night (USD)VRBO
In the Heart of Everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Lee Massachusettes! Located in the heart of the Berkshires, just 15 minutes to Tanglewood, 15 minutes to Jaco ...
From $268 per night (USD)VRBO
From $754 per night (USD)VRBO
Classic Antique Berkshire Farmhouse with heated pool and modern amenities.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 11
Our antique farmhouse is minutes from town, hiking, and swimming. The large fenced in yard has a private pool, treehouse ...
From $754 per night (USD)VRBO
From $395 per night (USD)VRBO
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
New 3 BR rustic-yet-elegantly modern 2300 sq ft country castle on 3+ secluded acres in Manor Lane, part of a private com ...
From $395 per night (USD)VRBO
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Charming cottage in Norman Rockwell's Stockbridge with two decks!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Light, sunny, charming 3-4 bedroom cottage built in 1832 in Norman Rockwell's Stockbridge, a five minute walk to the Red ...
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From $120 per night (USD)VRBO
Wyndham Bentley Brook-Ski In\/Out, Pool, Next to Jiminy Peak - Only 25% Deposit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
*Vrbo is currently experiencing technical issues related to displaying accurate information under “Rooms & beds.” The co ...
From $120 per night (USD)VRBO
From $287 per night (USD)Expedia
Featured in a Home & Garden TV Special 30 South Mountain Road
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Comfortable, quiet home in Pittsfield minutes from Tanglewood, Berkshire Theater Festivals and other year round attracti ...
From $287 per night (USD)Expedia
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Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sited in the original Ice House of the estate and grandly expanded, The Ice House Cottage is a delightful duplex, 2 bedr ...
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sweet dreams retreat
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Located near York Lake National Park and many other lakes. Equipped with everything you need for leisure or work. Includ ...
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From $493 per night (USD)VRBO
Best of the Berkshires & Hudson Valley
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Canaan, NY, less than a mile from the Massachusetts border, this wonderful 1700s post and beam farmhouse has ...
From $493 per night (USD)VRBO
From $727 per night (USD)Expedia
Lake House In The Heart Of The Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy a beautiful, serene getaway nestled in the heart of the Berkshires. Waking up steps to a clean, clear, spring fed ...
From $727 per night (USD)Expedia
From $620 per night (USD)VRBO
Renovated 1860's Farmhouse, across from the Miraval! Fenced in yard for dogs.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Ideally located just two minutes from the center of Lenox and across the street from the Miraval Resort and Spa. This e ...
From $620 per night (USD)VRBO
From $7446 per night (USD)Expedia
Charming Cabin On Scenic Road
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
One bedroom, one bathroom cottage on beautiful rural road. Wood burning stove and recently renovated kitchen makes it id ...
From $7446 per night (USD)Expedia
From $461 per night (USD)VRBO
Relaxing Getaway in the Beautiful Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A wonderful family country escape with all the accommodations of home! Set on two sprawling acres in the beautiful Berks ...
From $461 per night (USD)VRBO
From $708 per night (USD)Expedia
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Lakefront Home for Rent. Amazing location close to skiing, hiking, restaurants, Tanglewood and everything the Berkshires ...
From $708 per night (USD)Expedia
From $363 per night (USD)VRBO
Secluded Mountaintop Retreat in the Heart of the Berkshires
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
This secluded 6 acre property is just a 3 minute drive to the village of West Stockbridge. The house is set back from th ...
From $363 per night (USD)VRBO
From $302 per night (USD)Expedia
Spring\/Summer Mountain Spa Nature Retreat with 15 Acre Trail System
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This quiet ground floor residence located on 15 acres offers a modern rustic appeal. It includes a hot tub, dry sauna, a ...
From $302 per night (USD)Expedia
From $2286 per night (USD)VRBO
Iconic Cabin in the Berkshires
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 12
It’s hard to narrow down what is so special about this place. For each guest, it's likely something different. Maybe it’ ...
From $2286 per night (USD)VRBO
From $333 per night (USD)Expedia
Peaceful, Post and Beam Loft, Sleeps 9
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
Summary: Enjoy our lovely home for your next stay in the Berkshires! The list goes on but this house is the total packa ...
From $333 per night (USD)Expedia
From $438 per night (USD)VRBO
Best of the Berkshires + Hot Tub by Evergreen Home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Ski, hike, shop, and dine with this beautiful 2-bed, 1-bath Berkshires cottage as your home base. 7 minutes to downtown ...
From $438 per night (USD)VRBO
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Charming, Quiet, River Front
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
A cozy modern log cabin nestled in the hills of the Berkshires in a large wooded area with landscaped yard and fishpond. ...
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From $376 per night (USD)VRBO
Wildlife Lakeside Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Light and bright defines the newly renovated cabin boasting spectacular wood throughout and freshly decorated rooms. Ra ...
From $376 per night (USD)VRBO
From $267 per night (USD)Expedia
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: You want to pop out of bed, walk downstairs and be right on the mountain - this is the place to be. This Styli ...
From $267 per night (USD)Expedia
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One Bedroom Luxury Cottage at Blantyre, Relais & Châteaux
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Country chic in design, the Old Bath House is decorated in shades of coral, bisque and turquoise. A spacious living room ...
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Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located down a peaceful path lies a secluded two-bedroom cottage with period American furnishings and modern amenities o ...
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From $589 per night (USD)VRBO
Fox Hollow Luxury Ranch Laurel Lake
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 11
Awesome Berkshire Location. 1000 feet of Laurel Lake frontage shared with private dock , 2 canoes and 2 kayaks. Large o ...
From $589 per night (USD)VRBO
From $262 per night (USD)Expedia
Quiet & private small horse farm only 1.5 miles to Jiminy Peak. Pet friendly.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The entire second floor of our horse barn is 1000+ square feet of cozy enjoyment, featuring a queen bed in the bedroom, ...
From $262 per night (USD)Expedia
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The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This hotel/resort is at the base of the ski lift for Jiminy Mountain. And, when you are not on the slopes, it features a ...
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From $548 per night (USD)Expedia
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This hotel/resort is at the base of the ski lift for Jiminy Mountain. And, when you are not on the slopes, it features a ...
From $548 per night (USD)Expedia
From $280 per night (USD)VRBO
Berkshires 4br\/2ba, FALL, WINTER SKI JIMINY PK OR Long Term '25
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
BERKSHIRES - 4 BR/2BA - CHARMING, BEAUTIFULLY DECORATED (CHECK PHOTOS PLEASE) 1,800 sq. ft New England "farmhouse,'" 4 b ...
From $280 per night (USD)VRBO
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Beautiful farmhouse for perfect country escape - close to skiing, 5 fireplaces.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy upscale yet cozy accommodations in this 1734 farmhouse nestled in the northwest corner of Connecticut in the Litch ...
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From $292 per night (USD)VRBO
Lovely ranch home getaway in The Berkshires- just 6 miles to Tanglewood
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
This ranch home is in the heart of The Berkshires of Western Massachusetts, in the small town of Richmond. (West Stockbr ...
From $292 per night (USD)VRBO
From $869 per night (USD)Expedia
Stunning Berkshire custom luxury home in private wooded community- walk to lake
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 4
*******Perfect Home for 1 to 12 People******* 5 BR's with 2 King Beds + 2 Queen Beds + 4 Twin Beds ...
From $869 per night (USD)Expedia
From $419 per night (USD)VRBO
Little Gem On Baldwin Hill In South Egremont
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Shingled farmhouse with modern interior. Spacious & sunny kitchen that connects to the large outdoor patio with fireplac ...
From $419 per night (USD)VRBO
From $251 per night (USD)Expedia
Peace and quiet on the lake
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
OPEN FOR ALL THE WONDERFUL SEASONS! You will love the peaceful and private lake and have plenty of other great things t ...
From $251 per night (USD)Expedia
From $345 per night (USD)VRBO
Peaceful Woodland Home in the Heart of the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Residence is a beautiful, secluded home in the Berkshire foothills. The 14-acre property includes hiking trails thro ...
From $345 per night (USD)VRBO
From $239 per night (USD)VRBO
Comfortable, renovated 2 bedroom apartment in historic grist mill.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Renovated 2 bedroom (1 queen, 1 full) 2 bath 2nd floor apartment (stairs). Small kitchen w/refrigerator, 2 burner hotpla ...
From $239 per night (USD)VRBO
From $1260 per night (USD)VRBO
5Bdrm\/6Bath estate on Lenox - Stockbridge border, near BSO Tanglewood
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 20
Historic, elegant, recently renovated estate on 7 acres. BBQ grills outdoors. Near Jacob's Pillow Dance Festival, BSO ...
From $1260 per night (USD)VRBO
From $547 per night (USD)Expedia
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Prior guests of this charming house next to the forest trails have already reserved their return stay for next year to e ...
From $547 per night (USD)Expedia
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A four-season forest cabin
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
This home is the perfect answer to fit your vacationing needs at any time of year. Ski, snowboard, snowshoe, or other o ...
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From $578 per night (USD)Expedia
Water front log cabin next to Tanglewood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Log cabin in a very private setting on the water with a dock and access to the Stockbridge bowl. Waterfront property clo ...
From $578 per night (USD)Expedia
From $695 per night (USD)VRBO
Lakeside Berkshires Home Near Hiking & Skiing!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Escape to the Berkshires for a peaceful mountain respite at this charming, rustic 3-bedroom, 2-bath lakeside home. Choos ...
From $695 per night (USD)VRBO
From $386 per night (USD)Expedia
Spacious Comfortable Charming Family Farmhouse Great Location
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
ABOUT OUR PROPERTY: Experience a little of old New England. Our VRBO is a charming historic family farmhouse apartment( ...
From $386 per night (USD)Expedia
From $422 per night (USD)VRBO
Cozy Great Barrington Home ~ 1 Mi to Ski Resort!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Art and history meet breezy mountain adventures at this Great Barrington vacation rental! This 4-bedroom, 2-bathroom hou ...
From $422 per night (USD)VRBO
From $615 per night (USD)VRBO
Great Barrington 4BR home on 3 wooded acres walking distance to town!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
Bring the whole family to our Great Barrington home on 'The Hill'. With 4 bedrooms, 4 bathrooms, outdoor deck, screened ...
From $615 per night (USD)VRBO
From $166 per night (USD)VRBO
East Otis, MA, Waterfront Summer Cottage, Big Pond,
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Rental is weekly; Sunday to Sunday This charming waterfront cottage is approximately 110 feet from the water. It is loca ...
From $166 per night (USD)VRBO
From $358 per night (USD)Expedia
Cozy Log Cabin Retreat with Pool on 4 Acres
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gather at the log cabin in the woods and enjoy the private pool (Memorial Day - Sept). Updated with all the essentials l ...
From $358 per night (USD)Expedia
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Beautiful Berkshires Farmhouse with game room and plenty of room
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Our home offers families a place to come together and unwind. This home offers 4 bedrooms, 3 baths (1 with the most AMAZ ...
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From $350 per night (USD)Expedia
Walk to Dining: Downtown Lenox Guest House!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
2 Mi to Tanglewood | Private Yard w/ Grill | Dedicated Workspace This fully private 3-bedroom, 2.5-bath vacation rental ...
From $350 per night (USD)Expedia