Berkshire Area, Massachusetts Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Berkshire Area, Massachusetts on RentalSaver.com!

Berkshire Area Rentals

$Cozy Monterey Home w\/ Porch: Walk to Lake Garfield$
From $276 per night (USD)
VRBO
Cozy Monterey Home w\/ Porch: Walk to Lake Garfield
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Discover historic attractions and unbeatable outdoor recreation at this Monterey vacation rental featuring a stone patio ...
From $276 per night (USD)
VRBO
From $508 per night (USD)
Expedia
Elegant house nestled in the scenic hills of Northern Berkshire County.
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
TRAVELER REVIEWS: On January 2, 2018 Jill Staffin became the new property manager for the Manor. We wanted to make sure ...
From $508 per night (USD)
Expedia
From $420 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 $420 per night (USD)
VRBO
From $206 per night (USD)
Expedia
The Pocumtuck Cabin @ The Wigwam Western Summit
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Get outside! Romantic and private cabin for two located at the highest point of the western summit and just a few miles ...
From $206 per night (USD)
Expedia
From $206 per night (USD)
VRBO
The Mohawk Cabin @ Wigwam Western Summit
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Own the sunset while you stay in the Mohawk cabin. Enjoy the incredible view from your window and wake up with clouds un ...
From $206 per night (USD)
VRBO
From $197 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 $197 per night (USD)
Expedia
$Berkshires Home on 11 Acres w\/ Pond & 2 Fire Pits!$
From $447 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 $447 per night (USD)
VRBO
From $479 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, very quiet and sweet neighborhood of ...
From $479 per night (USD)
Expedia
From $349 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 $349 per night (USD)
VRBO
From $299 per night (USD)
Expedia
Charming Apartment In Berkshire Victorian Home
Bedrooms:
2
Bathrooms:
3
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 $299 per night (USD)
Expedia
From $393 per night (USD)
VRBO
Sun Filled Lenox Retreat-Minutes to Tanglewood
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Enjoy all the Berkshires has to offer from this charming 3BR/2BA home-base in Lenox. Drive 5 minutes to downtown Lenox & ...
From $393 per night (USD)
VRBO
From $269 per night (USD)
Expedia
Sweet Dreams Retreat
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Sandisfeild is a quiet peaceful place nestled in lush forest surrounded by wildlife. It's a beautiful place ...
From $269 per night (USD)
Expedia
From $499 per night (USD)
VRBO
* Private Berkshire Escape* Monthly Pricing Avail
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: Private home offering relaxation with a beautiful property. This cozy home will give you the comfort you need ...
From $499 per night (USD)
VRBO
From $960 per night (USD)
Expedia
Private mountain top Chalet, a short walk to Mass Moca. .
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Enjoy the privacy and spaciousness of the whole house. Each room uniquely decorated and super comfortable, with its own ...
From $960 per night (USD)
Expedia
From $642 per night (USD)
VRBO
The Gatehouse 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 $642 per night (USD)
VRBO
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Expedia
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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Expedia
From $999 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 $999 per night (USD)
VRBO
From $3550 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 Estate built in the 1880s for a U.S. Secretary of State and New Jersey State ...
From $3550 per night (USD)
Expedia
From $295 per night (USD)
VRBO
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 $295 per night (USD)
VRBO
$Gorgeous 3BR 3BA Sleeps 8 Ski On \/ Off Jiminy Peak-2000 Sq Ft Mountainside Condo$
From $499 per night (USD)
Expedia
Gorgeous 3BR 3BA Sleeps 8 Ski On \/ Off Jiminy Peak-2000 Sq Ft Mountainside Condo
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Right on the mountain, this spacious 1900 sq. ft. retreat Condo is your home away from home. It's the best way ...
From $499 per night (USD)
Expedia
From $1513 per night (USD)
VRBO
LAKE FRONT LAKE BUEL10 MIN GREAT BARRINGTON HOUSE VIEWS PRIVATE SWIM KAYAKING
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
SATURDAY TO SATURDAYS 5 MINUTES TO GREAT BARRINGTON. A SLICE OF HEAVEN. PRIVATE CUL DE SAC LAKEFRONT INCREDIBLE VIEWS. ...
From $1513 per night (USD)
VRBO
From $200 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 $200 per night (USD)
Expedia
$Cabin w\/3 Acres, Tennis+BBall Courts by 4 Ski Mtns$
From $349 per night (USD)
VRBO
Cabin w\/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Bedrooms:
3
Bathrooms:
4
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 $349 per night (USD)
VRBO
$Rustic Berkshires Cottage at Lake Buel w\/ Kayaks!$
From $165 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 $165 per night (USD)
Expedia
$'The Mill River Cabin’ w\/ Fireplace & River View!$
From $277 per night (USD)
VRBO
'The Mill River Cabin’ w\/ Fireplace & River View!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Reconnect with Mother Nature at this 2-bedroom, 1-bath cabin loaded with character! Minutes from the Historic Mill River ...
From $277 per night (USD)
VRBO
From $260 per night (USD)
Expedia
Waterfront Cottage: 10 Min to Great Barrington!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
A couple's getaway for the books awaits you at this Lake Buel vacation rental. Just 6 miles from Great Barrington's shop ...
From $260 per night (USD)
Expedia
From $1610 per night (USD)
VRBO
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 ...
From $1610 per night (USD)
VRBO
$Tranquil 3 BR Stockbridge House w\/ Private Deck!$
From $404 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 $404 per night (USD)
Expedia
From $338 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 $338 per night (USD)
VRBO
From $400 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 $400 per night (USD)
Expedia
From $395 per night (USD)
VRBO
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 $395 per night (USD)
VRBO
From $360 per night (USD)
VRBO
Historic 4-bedroom riverside home in Berkshires
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Elsewhere in the Berkshires was built in 1900 and thoughtfully redesigned in 2022. Tucked back from the road, t ...
From $360 per night (USD)
VRBO
From $867 per night (USD)
VRBO
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 $867 per night (USD)
VRBO
$Renovated Lakefront House w\/ Dock: Pets Welcome!$
From $731 per night (USD)
Expedia
Renovated Lakefront House w\/ Dock: Pets Welcome!
Bedrooms:
3
Bathrooms:
4
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 $731 per night (USD)
Expedia
From $375 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 $375 per night (USD)
VRBO
From $495 per night (USD)
Expedia
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
New 3 BR rustic-yet-elegantly modern 2150 sq ft country castle on 3+ secluded acres in Manor Lane, part of a private com ...
From $495 per night (USD)
Expedia
$Wyndham Bentley Brook-Ski In\/Out, Pool, Next to Jiminy Peak - Only 25% Deposit!$
From $149 per night (USD)
VRBO
Wyndham Bentley Brook-Ski In\/Out, Pool, Next to Jiminy Peak - Only 25% Deposit!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
*Vrbo is currently experiencing technical issues related to displaying accurate information under “Rooms & beds.” The co ...
From $149 per night (USD)
VRBO
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Expedia
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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Expedia
From $305 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 $305 per night (USD)
VRBO
From $256 per night (USD)
Expedia
Wildlife Cottage by the Lake
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Light and bright defines the newly renovated cabin boasting spectacular wood throughout and freshly decorated rooms. Ra ...
From $256 per night (USD)
Expedia
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VRBO
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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VRBO
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Expedia
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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Expedia
From $249 per night (USD)
VRBO
Berkshires Jiminy Peak Mountainside Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful two bedroom two bath fully furnished condominium style unit at Jiminy Peak. Home away from home! Fully furnis ...
From $249 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Lovely ranch home getaway in Berkshire County
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summer in The Berkshires is a beautiful time to rent this 2 bedroom, 2 bathroom ranch home in Richmond, Massachusetts. ...
From $270 per night (USD)
VRBO
From $300 per night (USD)
VRBO
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 $300 per night (USD)
VRBO
$Peaceful Family Home w\/ Fire Pit & Large Yard$
From $339 per night (USD)
Expedia
Peaceful Family Home w\/ Fire Pit & Large Yard
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Pack your cameras and prepare to experience the beauty of the Berkshires firsthand at this idyllic Williamstown vacation ...
From $339 per night (USD)
Expedia
From $379 per night (USD)
VRBO
Lakeside Berkshires Home Near Hiking & Skiing!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Escape to the Berkshires for a peaceful mountain respite at this charming, rustic 3-bedroom, 2-bath lakeside home. Choos ...
From $379 per night (USD)
VRBO
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Expedia
Cozy Great Barrington Home ~ 1 Mi to Ski Resort!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Art and history meet breezy mountain adventures at this Great Barrington vacation rental! This 4-bedroom, 2-bathroom hou ...
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Expedia
From $99 per night (USD)
VRBO
Morgan's Millhouse (Front)
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Morgan’s Millhouse! Located in the heart of Housatonic village, indulge the exquisitely serene atmosphere of ...
From $99 per night (USD)
VRBO
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Expedia
Entire home hosted by Morgan
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Welcome to Morgan’s Millhouse! Located in the heart of Housatonic village, indulge the exquisitely serene atmosphere of ...
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Expedia
From $317 per night (USD)
VRBO
Private Guest House in Dtwn Lenox, Walk to Dining!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This fully private 3-bedroom, 2.5-bath house is nestled in the heart of historic downtown Lenox - central to all the att ...
From $317 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Bedrooms:
1
Bathrooms:
1
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 $249 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Berkshire Lake at the Pillow
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. A front an ...
From $333 per night (USD)
VRBO
From $400 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 $400 per night (USD)
VRBO
From $217 per night (USD)
VRBO
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 $217 per night (USD)
VRBO
From $125 per night (USD)
Expedia
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 ...
From $125 per night (USD)
Expedia
From $75 per night (USD)
VRBO
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 $75 per night (USD)
VRBO
From $175 per night (USD)
Expedia
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 $175 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Beautiful, secluded, private resort in the heart of the Berkshires in Lenox, MA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A secluded resort nestled in the heart of the Berkshire Mountains, located in a scenic area where there is a wide variet ...
From $250 per night (USD)
VRBO
From $795 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 $795 per night (USD)
Expedia
From $225 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 $225 per night (USD)
VRBO
From $292 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 $292 per night (USD)
Expedia
From $149 per night (USD)
VRBO
Bright Boho Apt. in 18th c. Berkshire Farmhouse near Mt.Greylock & Jiminy Peak
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This bright 1BR/1BA is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in ...
From $149 per night (USD)
VRBO
$Private Estate w\/ Private Pool and Private Tennis Court - 5 mins to town!$
From $1346 per night (USD)
Expedia
Private Estate w\/ Private Pool and Private Tennis Court - 5 mins to town!
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 $1346 per night (USD)
Expedia
From $500 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 $500 per night (USD)
VRBO
$IN\/OUT SKIING CONDO , POOL, MOVIE THEATER\/ KIDS ACTIVITIES$
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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 ...
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Expedia
From $380 per night (USD)
VRBO
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 $380 per night (USD)
VRBO
From $129 per night (USD)
VRBO
Cozy Rustic Apt. in 18th c. Berkshire Farmhouse near Mt.Greylock & Jiminy Peak
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 $129 per night (USD)
VRBO
From $150 per night (USD)
VRBO
Lovely two bedroom river-view rental unit
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Comfortable, contemporary-styled, second-floor apartment with a view of the river. You'll have a great time relaxing ins ...
From $150 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Simple and Elegant 19th Century Williamstown Home
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Bring the whole family to this great place with lots of room inside and outside for fun. Enjoy a spacious living room wi ...
From $250 per night (USD)
Expedia
$Berkshires Getaway w\/ Deck & Mountain Views!$
From $276 per night (USD)
VRBO
Berkshires Getaway w\/ Deck & Mountain Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to this tranquil 2-bedroom, 1-bath Richmond apartment situated in the foothills of the Berkshires. Complete with ...
From $276 per night (USD)
VRBO
$Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On\/Off at Mountain Base$
From $162 per night (USD)
Expedia
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On\/Off at Mountain Base
Bedrooms:
1
Bathrooms:
1
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 $162 per night (USD)
Expedia
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VRBO
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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VRBO
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Expedia
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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Expedia
From $149 per night (USD)
VRBO
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 $149 per night (USD)
VRBO
$Wyndham Bentley Brook-Ski In\/Out, Pool, Next to Jiminy Peak - Only 25% Deposit!$
From $167 per night (USD)
VRBO
Wyndham Bentley Brook-Ski In\/Out, Pool, Next to Jiminy Peak - Only 25% Deposit!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
WHAT YOU’LL LOVE: Nestled among the Berkshire Mountains, you will find a true New England treasure; Wyndham Bentley B ...
From $167 per night (USD)
VRBO
From $395 per night (USD)
VRBO
Beautiful N. Adams-Williamstown Lake House-With Sat.-Sat. Stays in July & Aug
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 $395 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Mountain views & family fun! Spacious home two blocks from charming main street!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Experience the best of the Berkshires' natural beauty and small-town charm at Greylock Gables, our 4-bed / 2-bath coloni ...
From $280 per night (USD)
Expedia
From $267 per night (USD)
VRBO
Country Living just minutes from Everything! Now offering Seasonal Discounts!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
2 minutes to Bartlett's Apple Orchard, Richmond 5 minutes to Bousquet Ski Area, Pittsfield 6 minutes to Balderdash Cella ...
From $267 per night (USD)
VRBO
From $177 per night (USD)
Expedia
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Bedrooms:
1
Bathrooms:
1
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 $177 per night (USD)
Expedia
From $207 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 $207 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $613 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 $613 per night (USD)
VRBO
From $226 per night (USD)
Expedia
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 $226 per night (USD)
Expedia
$Wyndham Bentley Brook-Ski In\/Out, Indoor + Outdoor Pools - Only 25% Deposit!$
From $167 per night (USD)
VRBO
Wyndham Bentley Brook-Ski In\/Out, Indoor + Outdoor Pools - Only 25% Deposit!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
WHAT YOU’LL LOVE: Nestled among the Berkshire Mountains, you will find a true New England treasure; Wyndham Bentley B ...
From $167 per night (USD)
VRBO
From $208 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 $208 per night (USD)
Expedia
From $449 per night (USD)
VRBO
Private Berkshire County Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Beautiful home with private yard and heated pool. Exquisite summer setting and breathtaking fall foliage in th ...
From $449 per night (USD)
VRBO
From $399 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 $399 per night (USD)
VRBO
From $125 per night (USD)
VRBO
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Newly renovated unit with fireplace in main room, bathroom, bedroom (queen) and kitchenette.The unit also has a futon th ...
From $125 per night (USD)
VRBO
From $175 per night (USD)
Expedia
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 $175 per night (USD)
Expedia
$2 Bedroom\/2 Bath Vacation Rental in the Berkshires$
From $165 per night (USD)
VRBO
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 ...
From $165 per night (USD)
VRBO
From $212 per night (USD)
Expedia
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Come and enjoy the many adventures and activities that The Berkshires in Massachusetts has to offer. This cute 2 bedroo ...
From $212 per night (USD)
Expedia
From $299 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 $299 per night (USD)
VRBO
From $250 per night (USD)
Expedia
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 $250 per night (USD)
Expedia
From $249 per night (USD)
VRBO
Spacious waterfront Berkshire home family private get-away
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This renovated waterfront home offers incredible views. Big Pond is surrounded by dense forests and abuts state park lan ...
From $249 per night (USD)
VRBO
From $200 per night (USD)
Expedia
Elegant 19th Century New England 2BR vacation rental at Garfield House
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This super comfortable and spacious Berkshires getaway is located on Main St. in Lee, Massachusetts. The main level has ...
From $200 per night (USD)
Expedia
Click For Pricing
VRBO
Two Bedroom house in the heart of the Berkshires
Bedrooms:
1
Bathrooms:
2
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 ...
Click For Pricing
VRBO
From $280 per night (USD)
Expedia
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 $280 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Mountainside Condo @ Jiminy Peak in the Berkshires
Bedrooms:
4
Bathrooms:
2
Sleeps:
6
Treat yourself and be our guest at our terrific mountainside getaway, a private condo nestled at the base of Jiminy Peak ...
From $295 per night (USD)
VRBO
From $125 per night (USD)
Expedia
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 $125 per night (USD)
Expedia

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Results: 936 Rentals