Berkshire Area Rentals
From $331 per night (USD)VRBO
Cozy Monterey Home w\/ Porch: Walk to Lake Garfield
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Discover historic attractions and unbeatable outdoor recreation at this Monterey vacation rental featuring a stone patio ...
From $331 per night (USD)VRBO
From $438 per night (USD)Expedia
Cheerful 3-bedroom cottage with woodstove
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20 ...
From $438 per night (USD)Expedia
From $508 per night (USD)VRBO
Spacious Victorian in N. Adams-walk to Mass MoCA
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 9
Built in 1881, this historic, grand Victorian home is located in the heart of the Berkshires in North Adams, Massachuset ...
From $508 per night (USD)VRBO
From $351 per night (USD)Expedia
Charming Apartment In Berkshire Victorian Home
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
3rd Floor Penthouse Unit (3 bed/ 1.5 bath). This charming apartment is located in the heart of Pittsfield's Historical D ...
From $351 per night (USD)Expedia
From $460 per night (USD)VRBO
Berkshires Home on 11 Acres w\/ Pond & 2 Fire Pits!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
A beautiful retreat awaits you at this 3-bedroom, 3-bathroom vacation rental in the Berkshires! This Becket home is situ ...
From $460 per night (USD)VRBO
From $472 per night (USD)Expedia
The Freckled Hen's Berkshire Nest
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
My home is a sweet, cozy, private, and very clean farmhouse style Cape in the safe, and quiet neighborhood of Abbey Cour ...
From $472 per night (USD)Expedia
From $369 per night (USD)VRBO
Restored 1881 Farm House
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Beautifully renovated 1881 farm house minutes from down town Lenox. The Space: Quintessential Lenox Farmhouse ...
From $369 per night (USD)VRBO
From $301 per night (USD)VRBO
Romantic weekend getaway for two! featuring a fireplace and hot tub,
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
A romantic weekend away! featuring a fire place and hot tub. Enjoy our charming, king sized, super comfy 1-bedroom g ...
From $301 per night (USD)VRBO
From $754 per night (USD)VRBO
* Private Berkshire Escape* Monthly Pricing Avail
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Private home offering relaxation with a beautiful property. This cozy home will give you the comfort you need ...
From $754 per night (USD)VRBO
From $571 per night (USD)VRBO
Enjoy Spring in the Berkshires at this Lovely Home
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: "We are located in the heart of America's cultural epicenter known as the Berkshires. Known as the "Gatehouse" ...
From $571 per night (USD)VRBO
From $1443 per night (USD)VRBO
A Grand property in Historic Stockbridge
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 12
The Taggart House is an grand estate in the heart of The Berkshires. The property is a 5-minute walk to the center of St ...
From $1443 per night (USD)VRBO
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One block from Main St Stockbridge
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
2 Bedroom 2 Bath fully furnished home steps from Main St. This charming house has been totally renovated and has an open ...
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From $2143 per night (USD)VRBO
The Kemble- Built by a US Secretary of State in Lenox
- Bedrooms:
- 14
- Bathrooms:
- 13
- Sleeps:
- 35
The Kemble Berkshires is a registered Great Estatebuilt in the 1880s for a U.S. Secretary of State and New Jersey State ...
From $2143 per night (USD)VRBO
From $357 per night (USD)Expedia
Completely Renovated Historic Home in the Heart of the Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Our home was completely renovated in 2017. The fully equipped kitchen opens to the dining area where the table seats 6, ...
From $357 per night (USD)Expedia
From $549 per night (USD)VRBO
Gorgeous 3BR 3BA Sleeps 10 Ski On \/ Off Jiminy Peak-2000 Sq Ft Mountainside Con
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Right on the mountain, this spacious 2000 sq. ft. retreat Condo is your home away from home. It's the best way ...
From $549 per night (USD)VRBO
From $1403 per night (USD)Expedia
LAKE FRONT LAKE BUEL Monterey 10 M GREAT BARRINGTON HOUSE VIEWS PRIVATE DOCK
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
SATURDAY TO SATURDAYS 10 MINUTES TO GREAT BARRINGTON. A SLICE OF HEAVEN. PRIVATE CUL DE SAC LAKEFRONT INCREDIBLE VIEWS. ...
From $1403 per night (USD)Expedia
From $228 per night (USD)VRBO
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 $228 per night (USD)VRBO
From $441 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 $441 per night (USD)Expedia
From $224 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 $224 per night (USD)VRBO
From $305 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 $305 per night (USD)Expedia
From $335 per night (USD)VRBO
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 $335 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 $556 per night (USD)VRBO
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 $556 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 $414 per night (USD)VRBO
19th c. Barn in the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 4
- 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 $474 per night (USD)Expedia
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 ...
From $474 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 $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 $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
From $124 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 $124 per night (USD)VRBO
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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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From $349 per night (USD)Expedia
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 $349 per night (USD)Expedia
From $339 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 $339 per night (USD)VRBO
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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 $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 $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 $695 per night (USD)Expedia
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)Expedia
From $429 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 $429 per night (USD)VRBO
From $373 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 $373 per night (USD)Expedia
From $237 per night (USD)VRBO
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: You want to pop out of bed, walk outside, and be right on the mountain This 1BR 1 BA Ground Floor Unit Charmin ...
From $237 per night (USD)VRBO
From $405 per night (USD)Expedia
Berkshire Lake at the Pillow, and EV!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
At the intersection of New York. CT and MA, enjoy a newly finished Four Season Home with your own boat dock. Included 2 ...
From $405 per night (USD)Expedia
From $484 per night (USD)VRBO
Perfect Holiday Retreat, Completely Renovated, Central Location
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Our completely renovated farmhouse is set upon a hilltop overlooking downtown Lee. It is a perfect spot for culture, sp ...
From $484 per night (USD)VRBO
From $227 per night (USD)Expedia
Charming historic cottage on scenic road to Mt. Greylock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room scho ...
From $227 per night (USD)Expedia
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Cottage Retreat in Heart of the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
LIVING ROOM: Bright light and high ceilings with new couch, chairs, Sonos speakers, and more. KITCHEN: Fully-outfitted k ...
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From $79 per night (USD)Expedia
Apartment Newly Remodeled Super Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Large 2nd floor fully furnished apartment in 2 story corner house with plenty of parking and separate back entrance/stai ...
From $79 per night (USD)Expedia
From $192 per night (USD)VRBO
Apartment in Gorgeous Stonybrook Farm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This apartment is located in a renovated barn on a large private estate, centrally located in the heart of the Berkshire ...
From $192 per night (USD)VRBO
From $823 per night (USD)Expedia
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Bright and airy, cathedral ceiling, Post & Beam home situated in the heart of the Berkshires, minutes from Lenox, Tangle ...
From $823 per night (USD)Expedia
From $307 per night (USD)VRBO
North Getaway Cottage
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
A great place for vacationers and those seeking a remote work or school location with three work areas and a guest print ...
From $307 per night (USD)VRBO
From $335 per night (USD)Expedia
Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Our home is nestled on 2.6 acres in the heart of the Berkshires! We are within 2 miles to Tanglewood & Kripalu while ju ...
From $335 per night (USD)Expedia
From $220 per night (USD)VRBO
Bright Boho Apt in 18th c Berkshire Farmhouse
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Bright and clean apartment on flower farm in the mountains This bright 1BR/1BA is located at the base of Mount Greylock ...
From $220 per night (USD)VRBO
From $1221 per night (USD)Expedia
Premiere Berkshire Country Estate w\/ Private Pool & Tennis Court - 5 mins to GB!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
In 2016 Smithsonian Magazine deemed Great Barrington, "The Best Small Town in America." Manor Lane is a private French C ...
From $1221 per night (USD)Expedia
From $599 per night (USD)VRBO
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
The lakeside house is built on a 1.1 acre lot with view of Lake Garfield. It is only a few minutes walk to the town's b ...
From $599 per night (USD)VRBO
From $384 per night (USD)Expedia
IN\/OUT SKIING CONDO , POOL, MOVIE THEATER\/ KIDS ACTIVITIES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
2BEDROOM and 2 BATH CONDO. Master Bath has large whirlpool tub. also has full sized pull out couch and portable cribs a ...
From $384 per night (USD)Expedia
From $208 per night (USD)VRBO
Cozy Rustic Apt in 18th c Berkshire Farmhouse
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This cozy rustic studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built ...
From $208 per night (USD)VRBO
From $214 per night (USD)Expedia
Lovely two bedroom river-view rental unit
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Comfortable, contemporary-styled, second-floor apartment with a view of the river. You'll have a great time relaxing ins ...
From $214 per night (USD)Expedia
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Berkshires Apt w\/ Deck & Mtn Views!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Stream On-Site | Fire Pit | 6 Mi to Tanglewood Perfect for music enthusiasts, outdoorsy friends, or families seeking th ...
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From $532 per night (USD)Expedia
Private Berkshires Getaway Minutes to Ski Butternut
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Newly renovated 4 bedroom and 2 full bath home set back from the road is a peaceful oasis. 2 minute drive to Ski Buttern ...
From $532 per night (USD)Expedia
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Berkshire Get away
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Beautiful old home in Lee Massachusetts. Two bedrooms one bath on a quiet street in Lee Massachusetts. A front porch to ...
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From $175 per night (USD)Expedia
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring ...
From $175 per night (USD)Expedia
From $233 per night (USD)VRBO
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On\/Off at Mountain Base
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: You want to pop out of bed, walk downstairs, and be right on the mountain - this is the place for you. This 1B ...
From $233 per night (USD)VRBO
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Great mountain getaway
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 8
Berkshire getaway, close to all activites. Easily accessible first floor. Master on main floor. Fully furnished two base ...
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From $124 per night (USD)VRBO
Wyndham Bentley Brook-Ski In\/Out, Pool, Next to Jiminy Peak - Only 25% Deposit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
WHAT YOU’LL LOVE: Nestled among the Berkshire Mountains, you will find a true New England treasure; Wyndham Bentley B ...
From $124 per night (USD)VRBO
From $441 per night (USD)Expedia
Beautiful N. Adams-Williamstown Lake House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Windsor Cottage is a relaxing, lakeside retreat located on Windsor Lake in North Adams, MA where you can enjoy your own ...
From $441 per night (USD)Expedia
From $349 per night (USD)VRBO
Berkshires Getaway! Family-friendly retreat near hiking, museums, and more!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
<b>Your Cozy Berkshires Getaway Awaits!</b> Escape to the serene beauty of the Berkshires! Nestled in a peaceful, fami ...
From $349 per night (USD)VRBO
From $241 per night (USD)Expedia
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: You want to pop out of bed, walk downstairs, and be right on the mountain This 1BR 1 BA Ground Floor Unit righ ...
From $241 per night (USD)Expedia
From $281 per night (USD)VRBO
Hearts Desire is a furnished whole house in a small, colorful garden center.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated, one level house with 2 rooms with king sized beds, 1 queen size sleeper sofa. Fully furnished kitchen ...
From $281 per night (USD)VRBO
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Great house in Stockbridge
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Three bedroom house, one en suite on first floor(can be twin or king), two (both queen) on second floor sharing a bathro ...
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From $680 per night (USD)VRBO
Ski on ski off 1 Br loft condo in the village center with private gated parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Completely remodeled 1 Br loft condo with pull out sleeper sofa located steps from everything Jiminy has to offer.Unit f ...
From $680 per night (USD)VRBO
From $503 per night (USD)Expedia
Country Living just minutes from Everything!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
2 minutes to Bartlett's Apple Orchard, Richmond 5 minutes to Bousquet Ski Area, Pittsfield 6 minutes to Balderdash Cella ...
From $503 per night (USD)Expedia
From $278 per night (USD)VRBO
5 Minutes from Catamount Ski Area
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Cozy house conveniently located in a quiet area near the village of South Egremont. Fresh air, natures beauty all togeth ...
From $278 per night (USD)VRBO
From $124 per night (USD)VRBO
Wyndham Bentley Brook-Ski In\/Out, Indoor + Outdoor Pools - Only 25% Deposit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
WHAT YOU’LL LOVE: Nestled among the Berkshire Mountains, you will find a true New England treasure; Wyndham Bentley B ...
From $124 per night (USD)VRBO
From $357 per night (USD)VRBO
Peaceful and Private Setting
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Summary: Beautiful home with private yard and heated pool. Exquisite summer setting and breathtaking fall foliage in th ...
From $357 per night (USD)VRBO
From $151 per night (USD)Expedia
UNIQUE - 1BR Country Condo @ Jiminy Peak
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Come and enjoy this increditable country decor. Soak up this country cottage charm while sipping your coffee or tea with ...
From $151 per night (USD)Expedia
From $414 per night (USD)VRBO
Heart of Lenox Walk to Town Cozy Cottage!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
***WE HAVE 180+, 5-STAR REVIEWS ON AIRBNB*** The cottage is a 2-minute walk to Church St., right in the heart of Lenox. ...
From $414 per night (USD)VRBO
From $120 per night (USD)Expedia
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Newly renovated unit with fireplace in main room, bathroom, bedroom (queen) and kitchenette.The unit also has a futon th ...
From $120 per night (USD)Expedia
From $209 per night (USD)VRBO
2 Bedroom newly renovated townehouse, beautifully decorated at Garfield House
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Garfield House Vacation living for short or longer stays in a newly renovated townhouse is in close proximity to all Ber ...
From $209 per night (USD)VRBO
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2 Bedroom\/2 Bath Vacation Rental in the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the tranquility and comfort of a four-season country getaway. This newly renovated luxury vacation rental is house ...
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From $293 per night (USD)VRBO
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come and enjoy the many adventures and activities that The Berkshires in Massachusetts has to offer. This cute 2 bedroo ...
From $293 per night (USD)VRBO
From $387 per night (USD)VRBO
Two Blocks from the Red Lion Inn & next to Berkshire Theater
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
My place is close to Stockbridge center, Berkshire Theaters, Great Barrington, Lenox, and the Berkshires in general - gr ...
From $387 per night (USD)VRBO
From $289 per night (USD)VRBO
Cozy Berkshire cottage with fireplace.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Relax at this unique, tranquil getaway. Minutes from all the Berkshires' offer; Tanglewood, Bousquet and Jiminy Peak sk ...
From $289 per night (USD)VRBO
From $362 per night (USD)Expedia
Spacious waterfront Berkshire home family private get-away
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
This renovated waterfront home offers incredible views. Big Pond is surrounded by dense forests and abuts state park lan ...
From $362 per night (USD)Expedia
From $209 per night (USD)VRBO
Elegant 19th Century New England 2BR vacation rental at Garfield House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This super comfortable and spacious Berkshires getaway is located on Main St. in Lee, Massachusetts. The main level has ...
From $209 per night (USD)VRBO
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Two Bedroom house in the heart of the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Two bedrooms, living room-dinning room combo, and full kitchen with all you need for your stay. There is a full-sized be ...
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From $427 per night (USD)VRBO
Picturesque Cottage with Sunroom on Ashmere Lake!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Dive into the rich culture, adventure, and beauty of the Berkshires with this Lake Ashmere vacation rental cottage! Insi ...
From $427 per night (USD)VRBO
From $330 per night (USD)Expedia
Mountainside Condo @ Jiminy Peak in the Berkshires, Massachusetts Lodging Tax
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 6
Treat yourself and be our guest atour terrific mountainside getaway, a private condo nestled at the base of Jiminy Peak ...
From $330 per night (USD)Expedia
From $134 per night (USD)VRBO
Black Bear Mountain Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Black Bear Mountain Cottage is located in 2 acres of land surrounded by beautiful trees, fresh air and that amazing ...
From $134 per night (USD)VRBO
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Large hilltop villa with hot tub!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Escape to this spacious hilltop villa boasting breathtaking views of North Adams, Massachusetts. This stylish single fam ...
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From $564 per night (USD)VRBO
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Your Home Away from Home: Ski-In/Ski-Out Luxury at Jiminy Peak Welcome to our family’s cozy retreat at Jiminy Peak Ski ...
From $564 per night (USD)VRBO
From $611 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 $611 per night (USD)Expedia
From $463 per night (USD)VRBO
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $463 per night (USD)VRBO
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Beautiful Berkshire classic home nestled in a quiet peaceful area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Beautiful secluded house to rent for Berkshire getaway. Located near York Lake National Park and many other lakes. Equip ...
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From $370 per night (USD)VRBO
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 $370 per night (USD)VRBO
From $292 per night (USD)Expedia
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 $292 per night (USD)Expedia
From $280 per night (USD)VRBO
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 $280 per night (USD)VRBO
From $611 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 $611 per night (USD)Expedia
Click For PricingVRBO
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 ...
Click For PricingVRBO
From $547 per night (USD)Expedia
Modern Victorian Walk to Town \/ Close to 2 Ski Resorts!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Lovely 4 bedroom, sleeps 10. 3-story classic Victorian home in family-friendly neighborhood. Clean modern interiors and ...
From $547 per night (USD)Expedia
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Secluded 19th century Farmhouse with mountain views
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 15
Mayunsook Farm has been cherished by our family for seven generations. Once a working dairy farm, providing our family w ...
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Park Model Single Family double lofted private heaven on a pond
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
You can't beat this place for location. It is close to all things Berkshires - Tanglewood, Close to Apalachian trail, L ...
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