Berkshire Area Rentals
From $973 per night (USD)VRBO
Architectural Lenox Retreat with Pool and Sauna, minutes to Tanglewood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our Lenox home in the heart of the Berkshires, designed for guests who want beauty, comfort, privacy, and a s ...
From $973 per night (USD)VRBO
From $333 per night (USD)VRBO
Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This 2BR home can sleep up to ...
From $333 per night (USD)VRBO
From $281 per night (USD)VRBO
Unique Condo, Quiet Neighborhood, Walk to Town.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Two bedroom, two bathroom condominium in a two family house located in one of Lenox’s most convenient and quiet neighbor ...
From $281 per night (USD)VRBO
From $332 per night (USD)VRBO
Quiet Lake house with beautiful water views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Massachusetts lake house on beautiful Ashmere lake in the Berkshires. Living room and porch provide beautiful views of t ...
From $332 per night (USD)VRBO
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Retreat In The Woods
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This lovely home is located in a quiet corner of the northern Berkshires. It is located just over a mile from beautiful ...
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From $627 per night (USD)VRBO
Beautiful, peaceful modern home in a wooded area with town beach lake access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Supremely relaxing modern home in wooded setting with screened in outdoor porch as well as a firepit, patio and gas gri ...
From $627 per night (USD)VRBO
From $429 per night (USD)VRBO
Timberdoodle-a mountainside retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
CATAMOUNT SKI RESORT IS SEVEN MINUTES AWAY. 11 MILES TO SKI BUTTERNUT. HIGH SPEED FIBER OPTIC INTERNET Our vacation h ...
From $429 per night (USD)VRBO
From $407 per night (USD)VRBO
Converted Berkshire schoolhouse on a quiet river
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Renovated schoolhouse on a quiet river in the Berkshires. This is the perfect place to unwind. Great for families and fr ...
From $407 per night (USD)VRBO
From $584 per night (USD)VRBO
Secluded Family Home in Serene Stockbridge Woods
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
***WE ALSO HAVE 55 5-STAR REVIEWS ON AIRBNB*** ***NEW SUMMER DATES NOW OPEN*** Private Forest Retreat | Heart of the B ...
From $584 per night (USD)VRBO
From $455 per night (USD)VRBO
Renovated Colonial on the River! Fantastic Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Blue House on the Bend Built around 1820, the Blue House on the Bend, an historic eyebrow colonial located on an idyl ...
From $455 per night (USD)VRBO
From $515 per night (USD)VRBO
Cheerful 3-bedroom cottage with woodstove
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20 ...
From $515 per night (USD)VRBO
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Large duplex near MASSMoCA, MCLA (21)
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This gorgeous late 19th century Victorian duplex recently under went a complete renovation. Situated on a lovely quiet s ...
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From $331 per night (USD)VRBO
Stockbridge Village in Summer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This 1900 farmhouse in the village of Stockbridge offers all the convenience of walking to restaurants, shops, the Red L ...
From $331 per night (USD)VRBO
From $265 per night (USD)VRBO
Cozy Accommodations w/ Fireplace, Full Kitchen & More!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located on the resort property: At Mountainside, Village Center, Country Village, or Beaver Pond. Ideal for larger famil ...
From $265 per night (USD)VRBO
From $340 per night (USD)VRBO
Spacious, Family-Friendly Getaway w/ Full Kitchen & Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located on the resort property: At Mountainside, Village Center, or Country Village, Ideal for larger families and grou ...
From $340 per night (USD)VRBO
From $199 per night (USD)VRBO
Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
So much, So Close - Nestled in the Berkshires, a getaway to Jiminy Peak offers everything you need, so close to home. Sp ...
From $199 per night (USD)VRBO
Click For PricingVRBO
Private Island - Largest Fresh Water Reservoir in Mass
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Rustic.. Not fancy... It's a cabin... 2 bedroom, one with a Queen the other with twin bunkbeds... 2 couches could sleep ...
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From $309 per night (USD)Expedia
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Brand new log cabin. Charming, quiet with privacy. If peace and tranquility are one of your vacation objectives, then th ...
From $309 per night (USD)Expedia
From $546 per night (USD)VRBO
Twin Maple Farm: Charming Modern Farmhouse
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This updated 1920s farmhouse centrally located in the Berkshires is great for family vacations with a large backyard for ...
From $546 per night (USD)VRBO
From $292 per night (USD)VRBO
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Swiss chalet type house with exposed douglas fir beams. Back of home has all windows opening to deck and forest. 2 bedro ...
From $292 per night (USD)VRBO
From $211 per night (USD)VRBO
Ashmere Lakefront Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Second floor one bedroom/ one bathroom apartment overlooking Lake Ashmere Docks and Lake . Enjoy kayaking or paddle boar ...
From $211 per night (USD)VRBO
From $1780 per night (USD)VRBO
Swim All Day. Stroll to Dinner. Repeat.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Bring the family, we've got the pool, the hot tub, and the table. Plenty of room to cook, or not, as it's a short stroll ...
From $1780 per night (USD)VRBO
From $443 per night (USD)VRBO
Lovely Townhouse In Heart Of Lenox, 2 Bedroom, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Just steps from our historical town, enjoy a special location in our quiet family neighborhood. Lenox offers gourmet res ...
From $443 per night (USD)VRBO
From $278 per night (USD)VRBO
Garfield Townhouse in the Berkshires on Main St
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy Townhouse on Main St in Lee , the entrance to the Berkshires. The townhouse is two stories with 2 Bedrooms, 1 1/2 ...
From $278 per night (USD)VRBO
From $652 per night (USD)VRBO
The Freckled Hen's Berkshire Nest
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
My home is a sweet, cozy, private, and very clean farmhouse style Cape in the safe, and quiet neighborhood of Abbey Cour ...
From $652 per night (USD)VRBO
From $584 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 $584 per night (USD)VRBO
From $638 per night (USD)VRBO
Beautiful Home in AMAZING Berkshire Location
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Come nestle in the woods at this beautiful retreat in a PRIME location - 5 minutes to both downtown Lee and Stockbridge, ...
From $638 per night (USD)VRBO
From $1595 per night (USD)Expedia
Stunning Renovated Victorian
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Located in the beautiful Berkshires, MA, the 5000 sqf home is located in a desired neighborhood known as "the Hill.” The ...
From $1595 per night (USD)Expedia
From $431 per night (USD)VRBO
Bershire Home Rental: Enjoy Berkshire Fall Foliage
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful house in rural northern Berkshire County. Property sits on 8 acres of land, 4 acres mowed and maintained. Tw ...
From $431 per night (USD)VRBO
From $1620 per night (USD)VRBO
Historic (updated)1812 Federal brick house well situated in Berkshires with pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Historic fully updated brick house originally built in 1812 in the Berkshires in Western Massachusetts on one of the pre ...
From $1620 per night (USD)VRBO
From $559 per night (USD)VRBO
Stockbridge Village Cottage With Mountain View’s and walk to town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Old meets new in this lovely cottage, a short walk to the Red Lion Inn. Lots of light, comfortable furniture, beautiful, ...
From $559 per night (USD)VRBO
From $723 per night (USD)VRBO
Berkshire Lake Beauty-Modern Amenities On The Lake
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
This home has been 100% remodeled! With a beautiful spot directly on Lake Pontoosuc, the new kitchen, bathrooms, firepla ...
From $723 per night (USD)VRBO
From $308 per night (USD)VRBO
Rustic Waterfront Retreat With Private Dock, 2 kayaks & canoe. Air conditioner!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This A-frame cottage has private waterfront access with two single kayaks and a canoe. A new 12,000 btu air conditoner k ...
From $308 per night (USD)VRBO
From $589 per night (USD)VRBO
Beautiful four season lakeside log home close to all Berkshires attractions.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Very comfortable and private log home on a non motor lake. West facing (beautiful sunsets over the lake). Three bedrooms ...
From $589 per night (USD)VRBO
From $889 per night (USD)VRBO
*Winter Special* Lovely Home on Golden Hill
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: "We are located in the heart of America's cultural epicenter known as the Berkshires. Known as the "Gatehouse" ...
From $889 per night (USD)VRBO
From $312 per night (USD)VRBO
Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful gem has been lovingly cared for by our family for almost 20 years—and has served as a relaxing retreat al ...
From $312 per night (USD)VRBO
From $677 per night (USD)VRBO
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
One of a kind must see getaway. Berkshire Glamour meets Hollywood Rennaisance and Town & Country. This well-lit, newly r ...
From $677 per night (USD)VRBO
From $823 per night (USD)Expedia
Berkshires / Great Barrington Chic & Cozy, Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
*20% month-long and 10% week-long discount automatically applied. If you don't see it applied, please feel free to reach ...
From $823 per night (USD)Expedia
From $504 per night (USD)VRBO
In town 2 bedroom, one bath carriage barn. Sleeps 5.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Beautiful two bedroom, one bath carriage barn with balcony. Features a living room with cathedral ceilings, dining area ...
From $504 per night (USD)VRBO
From $367 per night (USD)VRBO
Romantic Berkshires Cottage - Stunning Views, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This unique cottage--30' away from our home on a fenced, three-acre property--has its own entrance and its own parking s ...
From $367 per night (USD)VRBO
From $471 per night (USD)VRBO
Vacation in a Berkshire Farmhouse
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our idyllic farmhouse in the beautiful Berkshires, where you’ll enjoy the tranquility and comfort of country ...
From $471 per night (USD)VRBO
From $481 per night (USD)Expedia
A roomy remodeled retreat close to MassMoCA
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Large Victorian house within walking distance to MassMOCA and downtown North Adams. Sleeps eight comfortably with two ba ...
From $481 per night (USD)Expedia
From $1403 per night (USD)VRBO
A Grand property in Historic Stockbridge
- Bedrooms:
- 7
- 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 $1403 per night (USD)VRBO
From $636 per night (USD)VRBO
Modern 4 bedroom lakefront house in The Berkshires.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
4 Bedroom lakefront house on beautiful Richmond Pond. All new kitchen appliances and bathrooms. Just steps from our bran ...
From $636 per night (USD)VRBO
From $277 per night (USD)VRBO
Woods & Windows - Treehouse for Adults - Near a Lake, Waterfall and Tanglewood!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Your Treehouse in the Berkshires A cozy, all-wood year round retreat - tucked away close to a waterfall — amidst fully ...
From $277 per night (USD)VRBO
From $487 per night (USD)VRBO
Berkshire lake house on lake Garfield, Monterey MA; private, 5 BR, sleeps 12
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Family vacation lake house on lake Garfield, Monterey MA. Beautiful lake location nestled in the hills of the Berkshires ...
From $487 per night (USD)VRBO
From $296 per night (USD)VRBO
Charming Cottage, New Marlborough Village Green in the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Cottage apartment is located in the Village of New Marlborough, Ma. We are on the Village Green. Across the road fro ...
From $296 per night (USD)VRBO
From $975 per night (USD)Expedia
Jaw dropping mountain & lake views in this stylish mountain home….
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, h ...
From $975 per night (USD)Expedia
From $702 per night (USD)VRBO
Enjoy comfortable elegance in this secluded grand home located in town
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Ideally located in the heart of the Berkshires on one acre of lovely private land, this five bedroom home offers a peace ...
From $702 per night (USD)VRBO
From $913 per night (USD)VRBO
Beautiful Farm House Near Family Ski Mountains And Other Fun Winter Activities
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This gorgeous farmhouse has four bedrooms each with a private full bathroom. There are six steps leading to the front do ...
From $913 per night (USD)VRBO
From $744 per night (USD)VRBO
Dock on Lake Garfield, 10 min to Butternut, Wifi, So Fun!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
RENOVATED Charm: 1920's cottage with 3 acres of natural surroundings. A short, 5 minute walk via nature trail and stai ...
From $744 per night (USD)VRBO
From $3901 per night (USD)Expedia
The Kemble- Built by a US Secretary of State in Lenox
- Bedrooms:
- 13
- 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 $3901 per night (USD)Expedia
From $1044 per night (USD)VRBO
Renovated Lenox Haus close to downtown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Summer 2027 - July or August - This Dutch colonial home with 3 bedrooms and 3 bathrooms is located in Schermerhorn Park ...
From $1044 per night (USD)VRBO
From $468 per night (USD)Expedia
Completely Renovated Historic Home in the Heart of the Berkshires
- Bedrooms:
- 2
- 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 $468 per night (USD)Expedia
From $403 per night (USD)VRBO
Farmhouse with views nestled among nature reserve
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This preserved 18th century farmhouse is situated on a picturesque 24 acre estate boasting southerly views of rolling hi ...
From $403 per night (USD)VRBO
From $712 per night (USD)VRBO
Large, family-friendly farmhouse located in the beautiful Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 7
- Sleeps:
- 14
Historical country farmhouse in the beautiful Berkshires Mountains of Western MA Rustic, traditional family home with an ...
From $712 per night (USD)VRBO
From $452 per night (USD)VRBO
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our beautiful property is a great place to relax and enjoy the company of friends and family. It has a large living room ...
From $452 per night (USD)VRBO
From $429 per night (USD)Expedia
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $429 per night (USD)Expedia
From $500 per night (USD)VRBO
Family vacation home in Great Barrington
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious house in excellent condition on 3 secluded acres in Great Barrington, the heart of the Southern Berkshires, ava ...
From $500 per night (USD)VRBO
From $438 per night (USD)VRBO
Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. NOW WITH SUPER HIGH SPEED INTERNET ...
From $438 per night (USD)VRBO
From $994 per night (USD)VRBO
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Feel at home in Williamstown in this Williams College legend! After housing generations of Williams students, Jake House ...
From $994 per night (USD)VRBO
From $880 per night (USD)VRBO
Custom Home on 9 scenic acres near small lake, Sleeps up to 16.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
The House - Set privately within the heart of the Berkshires, this sky lit, bright and immaculate year round home, will ...
From $880 per night (USD)VRBO
From $1627 per night (USD)VRBO
Gracious Williamstown Home with Pool
- Bedrooms:
- 3
- 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 $1627 per night (USD)VRBO
From $298 per night (USD)Expedia
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $298 per night (USD)Expedia
From $205 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 $205 per night (USD)VRBO
From $230 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 $230 per night (USD)Expedia
From $324 per night (USD)VRBO
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 $324 per night (USD)VRBO
From $598 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 $598 per night (USD)VRBO
From $346 per night (USD)VRBO
3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious living/kitchen area, located on a quiet street and central location walkable to campus and restaurants, museums ...
From $346 per night (USD)VRBO
From $416 per night (USD)Expedia
Stockbridge Home: Walk to Town Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to a lake retreat with this 3-bedroom, 2-bathroom vacation rental home in Stockbridge. Stockbridge Bowl's grassy ...
From $416 per night (USD)Expedia
From $867 per night (USD)VRBO
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 $867 per night (USD)VRBO
From $416 per night (USD)Expedia
Tranquil 3 BR Stockbridge House w/ Private Deck!
- Bedrooms:
- 1
- 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 $416 per night (USD)Expedia
From $426 per night (USD)VRBO
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 $426 per night (USD)VRBO
From $286 per night (USD)VRBO
Riverhouse on Rising Pond!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located between the villages of Stockbridge, Housatonic and Great Barrington. Most unique Riverhouse property located on ...
From $286 per night (USD)VRBO
From $494 per night (USD)VRBO
Serene Berkshire Artist's House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful, comfortable artist's house, that is tastefully furnished. Located on a very quiet 5 acre property abutting Mt ...
From $494 per night (USD)VRBO
From $643 per night (USD)Expedia
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 do ...
From $643 per night (USD)Expedia
From $464 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 $464 per night (USD)VRBO
From $308 per night (USD)Expedia
Home in Great Barrington
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
{STAND ALONE UNIT}. Central and Private!! Just steps away from historic downtown Great Barrington and ...
From $308 per night (USD)Expedia
From $370 per night (USD)VRBO
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
2 MIN TO JIMINY PEAK - right down the road and next door to RAMBLEWILD- #1 AERIAL ADVENTURE PARK IN THE BERKSHIRES! Clo ...
From $370 per night (USD)VRBO
From $585 per night (USD)VRBO
5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
NOTE: Our street name has changed to Woodland Hill (from Squaw Peak). Same house, same house number - different street ...
From $585 per night (USD)VRBO
From $461 per night (USD)VRBO
Beautiful Waterfront home with deep water dock on Onota Lake. Huge covered deck.
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $461 per night (USD)VRBO
From $328 per night (USD)VRBO
Spacious Victorian duplex near MASSMoCA, MCLA (19)
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This gorgeous late 19th century Victorian duplex recently under went a complete renovation. Situated on a lovely quiet s ...
From $328 per night (USD)VRBO
From $539 per night (USD)VRBO
Restful pastoral, kids-friendly house w/ gardens, views, swimming pool, sauna
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Contemporary house in a beautiful pastoral setting. Viking stove, wood-burning fireplace, gunite heated saltwater pool, ...
From $539 per night (USD)VRBO
From $641 per night (USD)VRBO
Elegant & private light-filled privacy
- Bedrooms:
- 2
- 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 $641 per night (USD)VRBO
From $428 per night (USD)VRBO
Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA
- Bedrooms:
- 1
- 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 $428 per night (USD)VRBO
From $1167 per night (USD)VRBO
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 13
Our 6BR home is super comfortable, designed for multiple families to share (beds for max 13 guests), up to date, and jus ...
From $1167 per night (USD)VRBO
From $848 per night (USD)VRBO
In the heart of the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This meticulously cared for home is just ideal for year-round or vacation living. Enjoy the private screen porch on sum ...
From $848 per night (USD)VRBO
From $1156 per night (USD)Expedia
Beautiful Berkshire Farm House on 160+ Acres
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 16
Don't hesitate reach out about availability even if dates look unavailable. We are happy to review avails with you. A w ...
From $1156 per night (USD)Expedia
From $646 per night (USD)VRBO
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 $646 per night (USD)VRBO
From $718 per night (USD)Expedia
Massachusetts Lake House w/ Dock - Pets Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
150’ Lakefront | Renovated | Flotilla of Watercraft for Adults and Children | Fenced-In Yard Waterfront on Lake Buel — ...
From $718 per night (USD)Expedia
From $294 per night (USD)VRBO
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 $294 per night (USD)VRBO
From $284 per night (USD)VRBO
COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Cool off in the awesome clean water at our lake and get away during the heat? We have the first week in August availabl ...
From $284 per night (USD)VRBO
From $874 per night (USD)VRBO
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 $874 per night (USD)VRBO
From $370 per night (USD)VRBO
Serene, Private Waterfront House --Perfect Summer Retreat!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy everything the Berkshires has to offer from this beautiful, secluded, nicely renovated waterfront house set on two ...
From $370 per night (USD)VRBO
From $502 per night (USD)VRBO
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
New 3 BR rustic-yet-elegantly modern 2300 sq ft country castle set on on 3.5 secluded acres in Manor Lane, a private com ...
From $502 per night (USD)VRBO
From $537 per night (USD)VRBO
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 ...
From $537 per night (USD)VRBO
From $401 per night (USD)VRBO
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 $401 per night (USD)VRBO
From $723 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 $723 per night (USD)VRBO
From $10587 per night (USD)VRBO
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 $10587 per night (USD)VRBO
From $861 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 right on the water. In the summer the whole family can swim, kayak, paddleboa ...
From $861 per night (USD)Expedia