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

$Wyndham Bentley Brook-Ski In\/Out, Indoor + Outdoor Pools - Only 25% Deposit!$
From $199 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 $199 per night (USD)
VRBO
From $363 per night (USD)
Expedia
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Come enjoy a quiet getaway in Western Massachusetts. 2 bedrooms, (3 beds, 1 Queen, 1 Double and 1 twin) 1 bath, open ki ...
From $363 per night (USD)
Expedia
From $327 per night (USD)
VRBO
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Greetings from John at the American House! This is the perfect getaway to destress and relax! This is an original Lincol ...
From $327 per night (USD)
VRBO
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Expedia
Stylish cottage close to great hiking trails and great art museums
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The cabin on Florida Mountain has a covered porch and a south facing terrace providing ample outdoor space in complete p ...
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Expedia
From $489 per night (USD)
VRBO
PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
I JUST purchased my dream house! I have been searching for a lake house in the Berkshires for years & when this came on ...
From $489 per night (USD)
VRBO
From $296 per night (USD)
Expedia
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
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 $296 per night (USD)
Expedia
From $642 per night (USD)
VRBO
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Open and bright retreat in beautiful setting with privacy and stunning lake views. Centrally located between Lenox and S ...
From $642 per night (USD)
VRBO
From $339 per night (USD)
Expedia
COZY CABIN IN BERKSHIRES RESORT
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
PERFECT COZY MOUNTAIN CABIN for a couple's getaway, a fun little trip with friends or with family to enjoy all offered b ...
From $339 per night (USD)
Expedia
From $427 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 $427 per night (USD)
VRBO
From $300 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 $300 per night (USD)
Expedia
From $360 per night (USD)
VRBO
Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Please enjoy our little slice of paradise! Perched just up the hill from Lake Garfield, The Hupi House offers a truly ma ...
From $360 per night (USD)
VRBO
$Half Moon by AvantStay | 4BR Cabin w\/ Large Deck & Yard$
From $513 per night (USD)
Expedia
Half Moon by AvantStay | 4BR Cabin w\/ Large Deck & Yard
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Kick back among the wooded hills of the Berkshires at Half Moon. The rustic exterior of this log cabin gives way to natu ...
From $513 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: The most unique Suite in the Berkshires - This gorgeous Disney Themed Hotel Room will bring Mickey Magic to our ...
From $250 per night (USD)
VRBO
From $509 per night (USD)
Expedia
Winterberry Lodge: NEWLY RENOVATED Spacious Berkshire Getaway at Jiminy Peak
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
FULLY RENOVATED FALL 2023. Beautiful Berkshire home with modern furnishings. This fabulous multi-level 3 bedroom house ...
From $509 per night (USD)
Expedia
From $434 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 $434 per night (USD)
VRBO
$Williamstown Rustic & Spacious Estate w\/ 4 Master Suites in Berkshire County$
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Expedia
Williamstown Rustic & Spacious Estate w\/ 4 Master Suites in Berkshire County
Bedrooms:
5
Bathrooms:
4
Sleeps:
14
This historic 3300 sq/ft mountain home has 4 master suites and 4.5 baths. It is perfectly set up for 2-3 families or one ...
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Expedia
From $807 per night (USD)
VRBO
Family-Friendly Hancock Home: Walk to Slopes!
Bedrooms:
3
Bathrooms:
6
Sleeps:
15
Situated in the town of Hancock, 'Whistling Birches' offers guests 4 bedrooms, 3 bathrooms, a prime location just steps ...
From $807 per night (USD)
VRBO
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Expedia
Beautiful Berkshire rental, rustic elegance, August through fall
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
4.5 acres overlooking Juniper pond, private setting, 11 minutes to Gt.Barrington, 35 minutes to Tanglewood. Charming lar ...
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Expedia
From $184 per night (USD)
VRBO
Available for Healthcare and long term stays welcome 3 miles from Hospital
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
If you are coming to the area to help in one of our Hospitals or Healthcare facility please contact us for booking optio ...
From $184 per night (USD)
VRBO
From $1355 per night (USD)
Expedia
Exclusive Estate, Heated Yearround Outdoor Pool
Bedrooms:
5
Bathrooms:
7
Sleeps:
17
Summary: Awaiting your next trip in our former horse farm turned luxury vacation rental, recently upgraded and re-furnis ...
From $1355 per night (USD)
Expedia
From $156 per night (USD)
VRBO
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 $156 per night (USD)
VRBO
From $835 per night (USD)
Expedia
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
Bedrooms:
7
Bathrooms:
7
Sleeps:
15
This charming former tavern and stage coach inn makes the perfect four season getaway. You'll feel like you've taken ove ...
From $835 per night (USD)
Expedia
From $322 per night (USD)
VRBO
Cozy retreat in beautiful country setting
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled at the base of October Mountain, this cozy retreat has all the comforts of home. Sit out on the deck and sip you ...
From $322 per night (USD)
VRBO
From $776 per night (USD)
Expedia
Hidden Oasis in the Mountains by Evergreen Home
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Escape with family & friends to this hidden oasis in the heart of the Berkshires. Enjoy the beautiful perennial garden ...
From $776 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
$2 Bedroom\/2 Bath Vacation Rental in the Berkshires$
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Expedia
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 ...
Click For Pricing
Expedia
From $547 per night (USD)
VRBO
Fickle Fox Farm. Daffodils are popping their heads up, summer is coming!
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Newly renovated three bedroom, two and half bath home on 6 bucolic acres in Canaan Valley, CT. Spend lazy summer days i ...
From $547 per night (USD)
VRBO
From $293 per night (USD)
Expedia
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)
Expedia
From $150 per night (USD)
VRBO
Vacation Village In The Berkshires 5 Star Resort - Suite B
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Gold Crown Resort! Spectacular mountain views, clubhouse, indoor pool, outdoor pool, game room, playground, kiddy pool, ...
From $150 per night (USD)
VRBO
From $179 per night (USD)
Expedia
Upstairs on Main with private bathroom
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This is our newest and most exciting unit. Before, it was a one bedroom with two small business offices on the same floo ...
From $179 per night (USD)
Expedia
From $393 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 $393 per night (USD)
VRBO
From $289 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 $289 per night (USD)
Expedia
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VRBO
Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Hi! Welcome to the Berkshires! Enjoy total privacy on a full acre property overlooking 200 acres of conservation land. W ...
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VRBO
From $739 per night (USD)
Expedia
Hip Renovated Mid Century 4 Bedroom on Long Bow Lake
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Drive down a lovely country dirt road to this recently renovated 4 bedroom, 2 bath mid century home on Long Bow Lake. Th ...
From $739 per night (USD)
Expedia
From $334 per night (USD)
VRBO
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 $334 per night (USD)
VRBO
From $237 per night (USD)
Expedia
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 $237 per night (USD)
Expedia
From $426 per night (USD)
VRBO
Quintessential 1860's Berkshire farmhouse with mountain views on 30 acres.
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Charming 1860's farmhouse with spectacular mountain & meadow views situated on more than 30 acres. Large, covered porch ...
From $426 per night (USD)
VRBO
From $582 per night (USD)
Expedia
Fantastic cottage in the Berkshire Mountains
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Our incredible 4 bedroom log cabin is situated on 2 beautiful secluded acres in picture perfect Monterey - the ultimate ...
From $582 per night (USD)
Expedia
From $377 per night (USD)
VRBO
Brooksong, the perfect Berkshires getaway
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
*All bookings are subject to COVID-19 regulations by the state of Massachusetts. *Until regulations change, all guests ...
From $377 per night (USD)
VRBO
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Expedia
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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Expedia
From $457 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 $457 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
From $295 per night (USD)
Expedia
Cozy Cottage on the Lake
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax in our rustic lake-front cottage for your next getaway in the Berkshires! Our small lake is perfect for kayaking, ...
From $295 per night (USD)
Expedia
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VRBO
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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VRBO
From $548 per night (USD)
Expedia
Jiminy Peak Mountainside Getaway in the Berkshires, Massachusetts Lodging Tax
Bedrooms:
6
Bathrooms:
3
Sleeps:
8
This beautiful 3 bedroom, 3 full bath condo nestled in a quiet cul-de-sac is a short hop to the bunny ski lift! Newly re ...
From $548 per night (USD)
Expedia
From $574 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 $574 per night (USD)
VRBO
From $706 per night (USD)
Expedia
Catamount, Zip Line, Private Setting, Book Now!
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Summary: Expertly renovated four bedroom house with views of Catamount, post and beam wood ceilings and a lovely centerp ...
From $706 per night (USD)
Expedia
$Beautiful 3BR river view, huge glass wall Log House -2200 sq\/ft$
From $328 per night (USD)
VRBO
Beautiful 3BR river view, huge glass wall Log House -2200 sq\/ft
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunny, specious log house on the river. The home has beautiful forest and river views through huge glass wall which is f ...
From $328 per night (USD)
VRBO
From $644 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 $644 per night (USD)
Expedia
From $288 per night (USD)
VRBO
Renovated Downtown 1bedroom
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The ...
From $288 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Historical Downtown 1bedroom
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The ...
From $315 per night (USD)
Expedia
From $756 per night (USD)
VRBO
Beautiful House In The Woods, Huge Yard, Hot Tub
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Come enjoy country living in all seasons – on 4+ acres on a private lane yet only minutes to Downtown Great Bar ...
From $756 per night (USD)
VRBO
From $469 per night (USD)
Expedia
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 $469 per night (USD)
Expedia
$Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On\/Off at Mtn$
From $250 per night (USD)
VRBO
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On\/Off at Mtn
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: This is the MOST UNIQUE suite in the Berkshires, specially designed for an incredible experience. The Master B ...
From $250 per night (USD)
VRBO
From $1135 per night (USD)
Expedia
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
Bedrooms:
5
Bathrooms:
6
Sleeps:
20
** Check out the Playhouse on the Netflix series The World's Most Amazing Vacation Rentals. It's included in the Gourmet ...
From $1135 per night (USD)
Expedia
$In the beautiful Berkshires, wheelchair-accessible home-20min toTanglewood \n\n\n$
From $568 per night (USD)
VRBO
In the beautiful Berkshires, wheelchair-accessible home-20min toTanglewood \n\n\n
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
A wonderful Berkshire vacation home for the entire family to enjoy! This charming and spotless home is fully wheelchair/ ...
From $568 per night (USD)
VRBO
From $597 per night (USD)
Expedia
Farmhouse-Loft -48 Main Street, Lenox, MA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located on Main Street in downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in ki ...
From $597 per night (USD)
Expedia
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VRBO
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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VRBO
From $616 per night (USD)
Expedia
Modern And Spacious Berkshires Retreat 5 bdrm 3 bath
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
This is a completely renovated 5 bedrooms and 3 baths house that is situated on a private street, 5 min drive to either ...
From $616 per night (USD)
Expedia
From $770 per night (USD)
VRBO
Waterfront Ashmere Lake House Near Berkshire Attractions
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Waterfront property on Ashmere Lake in Hinsdale, MA, with 4 bedrooms, an office, 3 bathrooms, screened in porch and a be ...
From $770 per night (USD)
VRBO
From $600 per night (USD)
Expedia
6 BR 'CAMP' House on Twin Lakes - Epic Historic Property
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
The perfect home for your big group or family, with a charming history! This beautiful, spacious vacation home was forme ...
From $600 per night (USD)
Expedia
From $647 per night (USD)
VRBO
Light, Airy And Fabulous
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
This is a special place and it’s 3 minutes to Lake Garfield and 12 minutes to Butternut Ski Area! It's a very pretty an ...
From $647 per night (USD)
VRBO
From $581 per night (USD)
Expedia
Spacious & Modern Berkshires Getaway
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
Absolutely stunning 2018 build less than 1 mile from downtown Stockbridge and an 8 minute drive to Ski Butternut and dow ...
From $581 per night (USD)
Expedia
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VRBO
Soulful, light-filled Berkshire home with gardens
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our beautifully renovated Victorian is located in Housatonic, a hamlet of Great Barrington and only 10 minutes to the ce ...
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VRBO
From $295 per night (USD)
Expedia
Central Haus (Group getaway on a quiet street)
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Beautifully designed house on a lovely, quiet street, with a view of Mt. Greylock. Three-minute drive to MassMoCA, six-m ...
From $295 per night (USD)
Expedia
$Lakefront Berkshires Retreat w\/ Deck, Dock & Boat!$
From $397 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 $397 per night (USD)
VRBO
From $315 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 $315 per night (USD)
Expedia
$WINTER\/SUMMER - ON 5 ACRES, PRIVATE LAKE GARFIELD DOCK, 5 MILES FROM BUTTERNUT$
From $740 per night (USD)
VRBO
WINTER\/SUMMER - ON 5 ACRES, PRIVATE LAKE GARFIELD DOCK, 5 MILES FROM BUTTERNUT
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
We have done all we can to think of everything to ensure a great stay. Please review and let us know if you have any qu ...
From $740 per night (USD)
VRBO
From $292 per night (USD)
Expedia
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 $292 per night (USD)
Expedia
From $334 per night (USD)
VRBO
51 Church Street, Lenox MA - One Bedroom Unit
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Refined getaway Newly renovated downtown space fully equipped for all your needs. The kitchen has an array of cooking es ...
From $334 per night (USD)
VRBO
From $395 per night (USD)
Expedia
Pristine Home In Becket Woods
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Summary: Peaceful home on two acres to come and enjoy nature and each other's company. The house features high ceilings, ...
From $395 per night (USD)
Expedia
From $622 per night (USD)
VRBO
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 $622 per night (USD)
VRBO
From $424 per night (USD)
Expedia
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 $424 per night (USD)
Expedia
From $582 per night (USD)
VRBO
Stockbridge Home, Come Experience The Berkshires!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Beautifully renovated three bedroom in Stockbridge with a great layout and energy throughout the home. In addi ...
From $582 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Modern Victorian Walk to Main Street
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 $408 per night (USD)
Expedia
Click For Pricing
VRBO
Berkshires Log Cabin by Evergreen Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The ultimate escape to peace & tranquility in the Berkshires! Set on 1.3 private acres, this cozy log cabin getaway is c ...
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VRBO
$The Studio\nmini home away from home in the Berkshires$
From $151 per night (USD)
Expedia
The Studio\nmini home away from home in the Berkshires
Bedrooms:
1
Bathrooms:
0
Sleeps:
0
The studio is in the front room of an historic house (circa 1830) on Main St, in Lee. convenient to all of the town's a ...
From $151 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.
Bedrooms:
3
Bathrooms:
5
Sleeps:
6
The Berkshire Gorge House is 15 minutes from Jiminy Peak Ski Area, 30 minutes to Bosquet’s Ski area in Pittsfield, an ho ...
From $250 per night (USD)
VRBO
$Ashley Falls Home w\/ Fire Pit: Hike & Ski!$
From $439 per night (USD)
Expedia
Ashley Falls Home w\/ Fire Pit: Hike & Ski!
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
Game Room | 2,734 Sq Ft | ~6 Mi to Campbell Falls State Park Whether you’re chasing waterfalls in the summer, leaf-peep ...
From $439 per night (USD)
Expedia
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VRBO
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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VRBO
From $288 per night (USD)
Expedia
Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful Berkshire condo within Jiminy Peak grounds. First Corner unit in Country Villages past the Country Inn with am ...
From $288 per night (USD)
Expedia
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VRBO
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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VRBO
From $390 per night (USD)
Expedia
Lenox - Walk to Town - Berkshire Home
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Come, enjoy the Berkshires! This cottage built in the 1950's has recently been completely renovated from stem to stern ...
From $390 per night (USD)
Expedia
From $1289 per night (USD)
VRBO
Renovated family friendly house close to everything and endless views
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Bright, comfortable house with pool and comfortable outdoor seating and eating areas, endless mountain views in front an ...
From $1289 per night (USD)
VRBO
From $663 per night (USD)
Expedia
Cozy escape in the trees of the Berkshires
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
We are thrilled to share our country escape with you and hope you enjoy it as much as we do. Set on 5 acres of land, wit ...
From $663 per night (USD)
Expedia
$4Br\/3bath Lakefront\/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi$
From $402 per night (USD)
VRBO
4Br\/3bath Lakefront\/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
Lakefront property with own dock on Otis Reservoir with beautiful views and garden. Great for fall foliage. For ski sea ...
From $402 per night (USD)
VRBO
From $184 per night (USD)
Expedia
Dancing Horse Lodge
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Dancing Horse Lodge is located on Horse Farm in the heart of the beautiful Berkshire Mountains with plenty of room for f ...
From $184 per night (USD)
Expedia
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VRBO
Full Week of Ski-in,Ski-out @ Jiminy Peak Club Whyndam Bently Brook in Berkshire
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Full week rental only, Feb. 18 (in at 3pm) to Feb 25(check out 11am) @ Club Whyndham Bently Brook Resort @ Jiminy Peak ...
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VRBO
From $357 per night (USD)
Expedia
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
Situated in the heart of the Berkshires, this 3-bed, 2-bath vacation rental offers a modern living space, a large yard a ...
From $357 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Houghton Hill: Style and History in the Berkshires
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Enjoy fresh air and warm sun at the top of Houghton Street. And it's an 8-minute walk to MASS MoCA and the town center. ...
From $357 per night (USD)
VRBO
From $1407 per night (USD)
Expedia
Lakeside Home With Pool-Completely Renovated
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
On beautiful Lake Pontoosuc, this 100% renovated home is complete with a heated outdoor pool! Every detail has been att ...
From $1407 per night (USD)
Expedia
From $641 per night (USD)
VRBO
Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Enjoy the Jiminy Peak Mountain Resort and explore the Berkshires during Spring, Summer, and Fall in this highly desirabl ...
From $641 per night (USD)
VRBO
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Expedia
Long term vacation rental. Quiet clean and comfortable all one level
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This is a all one level, 1st floor, 1bedroom & 1bathroom in a 2 family home. The property has been recently updated with ...
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Expedia
$East Otis Reservoir Cabin w\/ Porch - Walk to Lake!$
From $195 per night (USD)
VRBO
East Otis Reservoir Cabin w\/ Porch - Walk to Lake!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Fireplace | Grill | Board Games & Puzzles Nestled in the woods of East Otis, this 2-bedroom, 1-bathroom vacation rental ...
From $195 per night (USD)
VRBO
$Beautiful Two Bedroom, Ski In\/Out, Mountainside, Home away from Home!$
From $542 per night (USD)
Expedia
Beautiful Two Bedroom, Ski In\/Out, Mountainside, Home away from Home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Jiminy Peak - This beautiful and premium condo was just renovated for the 2016 ski season. It is fully equipped with eve ...
From $542 per night (USD)
Expedia
From $259 per night (USD)
VRBO
COME STAY AT THE SHEFFIELD CHALET!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Bring friends or the whole family to this cozy accessible Berkshire County Country getaway. Only 5 minutes to Great Barr ...
From $259 per night (USD)
VRBO
From $813 per night (USD)
Expedia
Perfect for Winter Skiing!!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Perfect family home for all Winter activities with 4 Bedrooms and 3.5 baths, plus it is central to all the cultural act ...
From $813 per night (USD)
Expedia
From $475 per night (USD)
VRBO
12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Beautiful country home with 3 bedrooms plus a kids loft, 6 minutes to Great Barrington with lots to discover. 12 minutes ...
From $475 per night (USD)
VRBO
$Beautiful Timber Frame Home in the Berkshires \/Available for Long Term$
From $475 per night (USD)
Expedia
Beautiful Timber Frame Home in the Berkshires \/Available for Long Term
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The house is a newly constructed cruck timber frame designed by Jack Soban made from naturally treated local pine with c ...
From $475 per night (USD)
Expedia

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