Berkshire Area Rentals
From $338 per night (USD)VRBO
Huge Designer House on 2 acres property, minutes to restaurants, museums
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Huge 3 bedroom 2 bath designer house sitting on 2 acres land in Lenox. Three hours from NYC and two from Boston. All mus ...
From $338 per night (USD)VRBO
From $375 per night (USD)Expedia
New Listing Contemporary Cottage in the Woods viewing 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 $375 per night (USD)Expedia
From $344 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 $344 per night (USD)VRBO
From $245 per night (USD)Expedia
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 $245 per night (USD)Expedia
From $1067 per night (USD)VRBO
Hollywood Hills in the Berkshires
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 5
Glamorous modern hilltop living. After a day laying by the pool, enjoy a bottle of wine by the fireplace, take a soak i ...
From $1067 per night (USD)VRBO
From $209 per night (USD)Expedia
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 $209 per night (USD)Expedia
From $255 per night (USD)VRBO
Quiet Lake house with beautiful water views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Massachusetts lake house on beautiful Ashmere lake in the Berkshires. Living room and porch provide beautiful views of t ...
From $255 per night (USD)VRBO
From $278 per night (USD)Expedia
Perfect Vacation Get Away - Historical New Marlborough
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Quaint cottage in Southern Berkshire nestled in the historic district of New Marlborough. Cottage sits on 3 acres all o ...
From $278 per night (USD)Expedia
From $550 per night (USD)VRBO
Wyndham Bentley Brook Jiminy Peak ski in\/out unit
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Jiminy Peak Ski in/ski out in Winter. Summer activities at Jiminy Peak in the Berkshires. Fully equipped kitchen, livin ...
From $550 per night (USD)VRBO
From $210 per night (USD)Expedia
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 ...
From $210 per night (USD)Expedia
From $508 per night (USD)VRBO
Beautiful, peaceful modern home in a wooded area with lake access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Supremely relaxing modern home in wooded setting with screened in outdoor porch as well as a firepit, patio and gas gri ...
From $508 per night (USD)VRBO
From $390 per night (USD)Expedia
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 6
A Writer’s Haven!!! 360-degree scenic PRIVACY. YET… just 1/2 mile off the Mass Pike and 15 minutes from Tanglewood, Len ...
From $390 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 $415 per night (USD)Expedia
Timberdoodle-a mountainside treehouse
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
CATAMOUNT SKI RESORT IS ON THE OTHER SIDE OF THE MOUNTAIN. 11 MILES TO SKI BUTTERNUT. HIGH SPEED FIBER OPTIC INTERNET ...
From $415 per night (USD)Expedia
From $259 per night (USD)VRBO
Converted Berkshire schoolhouse on a quiet river
- Bedrooms:
- 2
- 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 $259 per night (USD)VRBO
From $555 per night (USD)Expedia
Secluded Family Home in Serene Stockbridge Woods
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
***WE ALSO HAVE 31 5-STAR REVIEWS ON AIRBNB*** ***NEW SUMMER DATES NOW OPEN*** Private Forest Retreat | Heart of the B ...
From $555 per night (USD)Expedia
From $346 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 $346 per night (USD)VRBO
From $441 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 $441 per night (USD)Expedia
From $436 per night (USD)VRBO
Newly Renovated Home With All The Modern Amenities
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
The perfect spot for a Berkshire getaway! This renovated home has all the old charm while offering a comfortable modern ...
From $436 per night (USD)VRBO
From $353 per night (USD)Expedia
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 ...
From $353 per night (USD)Expedia
From $338 per night (USD)VRBO
Stockbridge Vacation by Norman Rockwell
- 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 $338 per night (USD)VRBO
From $318 per night (USD)Expedia
Cozy Accommodations w\/ Fireplace, Full Kitchen & More!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located on the resort property: At Mountainside, Village Center, Country Village, or Beaver Pond. Ideal for larger famil ...
From $318 per night (USD)Expedia
From $388 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 $388 per night (USD)VRBO
From $214 per night (USD)Expedia
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 $214 per night (USD)Expedia
From $674 per night (USD)VRBO
Private Island - Largest Fresh Water Reservoir in Mass....
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Rustic.. Not fancy... It's a cabin... 2 bedroom, one with Queen the other with twin bunkbeds... 2 couches could sleep ex ...
From $674 per night (USD)VRBO
From $247 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 $247 per night (USD)Expedia
From $506 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 $506 per night (USD)VRBO
From $264 per night (USD)Expedia
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 $264 per night (USD)Expedia
From $177 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 $177 per night (USD)VRBO
From $348 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 $348 per night (USD)Expedia
From $1165 per night (USD)VRBO
Hang By The Pool or Walk To Town
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Available Friday June 28th - Friday July 12th '24. Heated pool, gourmet kitchen and a short walk to town. Restored to i ...
From $1165 per night (USD)VRBO
From $508 per night (USD)Expedia
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 $508 per night (USD)Expedia
From $315 per night (USD)VRBO
Lovely Townhouse In Heart Of Lenox
- 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 $315 per night (USD)VRBO
From $209 per night (USD)Expedia
Garfield Townhouse in the Berkshires on Main St
- Bedrooms:
- 2
- 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 $209 per night (USD)Expedia
From $164 per night (USD)VRBO
Studio Loft in the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Loft-at-Sea is a 800 Sq. Ft open floor plan studio apartment with plenty of light from three skylights and a picture win ...
From $164 per night (USD)VRBO
From $514 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 $514 per night (USD)Expedia
From $384 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 $384 per night (USD)VRBO
Click For PricingExpedia
Cozy two-bedroom ranch 15 minutes from Butternut Ski Resort - 90-day minimum
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy our comfortable, cozy, fully furnished two-bedroom, two-bathroom ranch (1,500 square-feet) in the Berkshires (Mont ...
Click For PricingExpedia
Click For PricingVRBO
Berkshire Ski House \/ Pittsfield
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Close to several popular family friendly Berkshire ski areas. Theaters restaurants and shopping are all walking distan ...
Click For PricingVRBO
From $642 per night (USD)Expedia
Beautiful Home in AMAZING Berkshire Location
- Bedrooms:
- 3
- 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 $642 per night (USD)Expedia
From $469 per night (USD)VRBO
Rustic Getaway with Extraordinary Vista
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
With exceptional lighting, Sky House overlooks a gorgeous , sloping yard in peaceful Monterey. Close to Lake Garfield an ...
From $469 per night (USD)VRBO
From $298 per night (USD)Expedia
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 $298 per night (USD)Expedia
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 $1181 per night (USD)Expedia
Stunning Renovated Victorian
- Bedrooms:
- 5
- 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 $1181 per night (USD)Expedia
From $563 per night (USD)VRBO
Great Barrington Get Away
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming home steps away from downtown Great Barrington. Lots of modern amenities, close to all the fantastic cultural ...
From $563 per night (USD)VRBO
From $377 per night (USD)Expedia
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 $377 per night (USD)Expedia
From $1370 per night (USD)VRBO
Historic (updated)1812 Federal brick house well situated in Berkshires with pool
- Bedrooms:
- 4
- 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 $1370 per night (USD)VRBO
From $442 per night (USD)Expedia
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 $442 per night (USD)Expedia
From $225 per night (USD)VRBO
Charming Berkshire Getaway in a Modern Comfortable House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Beautiful 3 bedroom ranch style house decorated in mid century modern style. Kitchen and bathrooms are brand new along w ...
From $225 per night (USD)VRBO
From $745 per night (USD)Expedia
Berkshire Lake Beauty-Modern Amenities On The Lake
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
This home has been 100% remodeled! With a beautiful spot directly on Lake Pontoosuc, the new kitchen, bathrooms, firepla ...
From $745 per night (USD)Expedia
From $247 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 $247 per night (USD)VRBO
From $451 per night (USD)Expedia
Beautiful four season lakeside log home close to all Berkshires attractions.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Very comfortable and private log home on a non motor lake. West facing (beautiful sunsets over the lake). Three bedrooms ...
From $451 per night (USD)Expedia
From $703 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 $703 per night (USD)VRBO
From $247 per night (USD)Expedia
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 $247 per night (USD)Expedia
From $558 per night (USD)VRBO
Art House! Spacious Getaway By Mass Moca
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 10
This newly renovated Victorian curated by the local Grant Larkin Design Team is a great space for large groups, with eas ...
From $558 per night (USD)VRBO
From $516 per night (USD)Expedia
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
One of a kind must see getaway. Berkshire Glamour meets Hollywood Rennaisance and Town & Country. This well-lit, newly r ...
From $516 per night (USD)Expedia
From $205 per night (USD)VRBO
Lake Community - Near Town, Attractions
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A short drive from New York City or Boston, or a flight into Hartford or Albany and you're in a new world of peacefulnes ...
From $205 per night (USD)VRBO
From $662 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* An inspiring renovated historic home with chic and th ...
From $662 per night (USD)Expedia
From $397 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 $397 per night (USD)VRBO
From $419 per night (USD)Expedia
Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This two bedroom condo in the Mountainside area is one of the most luxurious and appealing places to stay at Jiminy Peak ...
From $419 per night (USD)Expedia
From $292 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 $292 per night (USD)VRBO
From $403 per night (USD)Expedia
Vacation in a Berkshire Farmhouse
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 10
Welcome to our idyllic farmhouse in the beautiful Berkshires, where you’ll enjoy the tranquility and comfort of country ...
From $403 per night (USD)Expedia
From $391 per night (USD)VRBO
A Charming Mid 1800's Stockbridge Farmhouse.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Transform yourself in to the middle of a Norman Rockwell painting. It is easy to see how so many of his paintings were i ...
From $391 per night (USD)VRBO
From $790 per night (USD)Expedia
Lenox, private setting, close to Tanglewood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautifully furnished, well-located Lenox home has a brand new kitchen ! Central Air Conditioning, a King bed in b ...
From $790 per night (USD)Expedia
From $350 per night (USD)VRBO
A roomy remodeled retreat close to MassMoCA
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Large Victorian house within walking distance to MassMOCA and downtown North Adams. Sleeps eight comfortably with two ba ...
From $350 per night (USD)VRBO
From $1443 per night (USD)Expedia
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)Expedia
From $676 per night (USD)VRBO
Modern 4 bedroom lakefront house in The Berkshires.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
4 Bedroom lakefront house on beautiful Richmond Pond. All new kitchen appliances and bathrooms. Just steps from our bran ...
From $676 per night (USD)VRBO
From $285 per night (USD)VRBO
Berkshires Living!! Beautiful Location, Breathtaking Sunsets, Fully Reno Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy your own private summer mountaintop in the Berkshires - Two story, completely renovated air conditioned home on ...
From $285 per night (USD)VRBO
From $417 per night (USD)VRBO
Berkshire lake house on lake Garfield, Monterey MA; private, 5 BR, sleeps 12
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Family vacation lake house on lake Garfield, Monterey MA. Beautiful lake location nestled in the hills of the Berkshires ...
From $417 per night (USD)VRBO
From $349 per night (USD)Expedia
Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to the Berkshires and step back in time with a stay in our charming historic home, conveniently located near the ...
From $349 per night (USD)Expedia
From $263 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 $263 per night (USD)VRBO
From $814 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 $814 per night (USD)Expedia
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $693 per night (USD)Expedia
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 $693 per night (USD)Expedia
From $770 per night (USD)VRBO
'Village View'- Elegant, Comfortable, Historic Home in Downtown Lenox
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
"Village View", our 140 year old house, is at the end of a quiet street in downtown Lenox. The shops, restaurants, galle ...
From $770 per night (USD)VRBO
From $775 per night (USD)Expedia
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. Each bedroom has a queen size bed, sitting ...
From $775 per night (USD)Expedia
From $495 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 $495 per night (USD)VRBO
From $2779 per night (USD)Expedia
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 $2779 per night (USD)Expedia
From $784 per night (USD)VRBO
Renovated Lenox Haus close to downtown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
This Dutch colonial home with 3 or 4 bedrooms is located in Schermerhorn Park in a quiet neighborhood setting on a dead ...
From $784 per night (USD)VRBO
From $713 per night (USD)Expedia
Renovated Pittsfield Colonial by Evergreen Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This charming, newly remodeled Colonial home, nestled in the heart of the Berkshires, is perfect for your next family re ...
From $713 per night (USD)Expedia
From $516 per night (USD)VRBO
LUXURY BERKSHIRES RETREAT - Family Compound! - 2 separate but attached homes!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
5 bedrooms plus Queen sleeper- sleeps 12! Step away from the insanity of the modern world here in our oasis. Just minut ...
From $516 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 $367 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 $367 per night (USD)VRBO
From $535 per night (USD)Expedia
Large, family-friendly farmhouse located in the beautiful Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 14
Historical country farmhouse in the beautiful Berkshires Mountains of Western MA Rustic, traditional family home with an ...
From $535 per night (USD)Expedia
From $233 per night (USD)VRBO
mountain refuge
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Extended stays are welcome! Stay in our little Mobile Home, clean, sweet and unique. The house is adjacent to Breakshir ...
From $233 per night (USD)VRBO
From $326 per night (USD)Expedia
Beautiful Mountainside House with nearby Lake and Hiking Trails
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our secluded property is a great place to relax and enjoy the company of your friends and family. The house has all the ...
From $326 per night (USD)Expedia
From $535 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 $535 per night (USD)VRBO
From $415 per night (USD)Expedia
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 $415 per night (USD)Expedia
From $1403 per night (USD)VRBO
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)VRBO
From $181 per night (USD)Expedia
East Otis, MA, Waterfront Summer Cottage, Big Pond,
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Rental is weekly: Sunday to Sunday. This charming waterfront cottage is located on the pristine 333 acre lake known as B ...
From $181 per night (USD)Expedia
From $242 per night (USD)VRBO
Lakefront Cottage In The Berkshires In Western Massachusetts
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
INSIDE 650-square foot charming cottage directly on 129-acre Center Pond in Becket, MA. One main bedroom upstairs with q ...
From $242 per night (USD)VRBO
From $1215 per night (USD)Expedia
Spectacular Private Hilltop Contemporary Estate (Pool\/Catamount\/Bash Bish Fall)
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
This fully renovated contemporary estate has it all to make it your place to escape all year round. Sitting on 11 pri ...
From $1215 per night (USD)Expedia
From $408 per night (USD)VRBO
Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!
- Bedrooms:
- 4
- 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 $408 per night (USD)VRBO
From $977 per night (USD)Expedia
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Feel at home in Williamstown in this Williams College legend! After housing generations of Williams students, Jake House ...
From $977 per night (USD)Expedia
From $642 per night (USD)VRBO
Custom Home In Scenic Wooded Area near small lake, Sleeps up to 16
- Bedrooms:
- 3
- 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 $642 per night (USD)VRBO
From $576 per night (USD)Expedia
Wyndham Bentley Brook Condo Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Enjoy great year round activities from white water rafting and hiking in the summer, to skiing at the famous Jiminy Peak ...
From $576 per night (USD)Expedia
From $1139 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 $1139 per night (USD)VRBO
From $399 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 $399 per night (USD)Expedia
From $227 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 $227 per night (USD)VRBO
From $333 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 $333 per night (USD)Expedia