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

From $582 per night (USD)
VRBO
Lakeshore cabin with private beach and dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
A classic Berkshire cabin nestled under maple trees, on the shore of the Stockbridge Bowl cove. Serene, peaceful and pri ...
From $582 per night (USD)
VRBO
$Cozy 3BR Home w\/ Yard & Patio 5 min to Tanglewood$
From $399 per night (USD)
Expedia
Cozy 3BR Home w\/ Yard & Patio 5 min to Tanglewood
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Step back in time within this striking 1900s Colonial-style home, a mere 7-10 minute walk from Lenox’s charming downtown ...
From $399 per night (USD)
Expedia
$4BR Home w\/ Yard & BBQ, 5 min walk to downtown Lee$
From $386 per night (USD)
VRBO
4BR Home w\/ Yard & BBQ, 5 min walk to downtown Lee
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Nestled on an expansive and well-manicured 0.46-acre lot, this pet-friendly, 4-bedroom home presents a tantalizing mix o ...
From $386 per night (USD)
VRBO
$Colonial House, w\/Yard,7min walk to Downtown Lenox$
From $424 per night (USD)
Expedia
Colonial House, w\/Yard,7min walk to Downtown Lenox
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A peaceful retreat with a timeless aura, this revamped 19th-century home is brimming with old-school charm–combining col ...
From $424 per night (USD)
Expedia
$Private Lake Cottage on 3 acres w\/350 sq. ft. deck\n$
From $395 per night (USD)
VRBO
Private Lake Cottage on 3 acres w\/350 sq. ft. deck\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Surround yourself in the natural beauty of the historic Berkshires at our 1504 sq. ft. gem, nestled on an expansive 3-ac ...
From $395 per night (USD)
VRBO
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Expedia
Stylish Berkshire Apartment conveniently located in the center of town
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Enjoy a stylish, all inclusive experience at this centrally-located apartment. Located in downtown Pittsfield, Ma. A q ...
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Expedia
From $486 per night (USD)
VRBO
Stay Lakeside This Summer!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Summary: Secluded lakefront bliss, retreat in Great Barrington! Sleeps six with modern amenities, scenic views, and outd ...
From $486 per night (USD)
VRBO
From $725 per night (USD)
Expedia
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
At the base of Jiminy Peak Ski Mountain, an exceptional choice for mountainside play with access to ski lifts and equipm ...
From $725 per night (USD)
Expedia
From $725 per night (USD)
VRBO
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
At the base of Jiminy Peak Ski Mountain, an exceptional choice for mountainside play with access to ski lifts and equipm ...
From $725 per night (USD)
VRBO
From $794 per night (USD)
Expedia
Lakeside 5-BR Home in Idyllic Berkshires
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: Come enjoy time with friends and family in this newly renovated 5-BR home located along Long Bow Lake in the Be ...
From $794 per night (USD)
Expedia
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VRBO
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Set amid a mountain haven, Bentley Brook Ski Oasis delivers an unmatched winter sanctuary. With seamless ski access, thi ...
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VRBO
$Bentley Brook Alpine Haven: Premier Ski-In\/Ski-Out$
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Expedia
Bentley Brook Alpine Haven: Premier Ski-In\/Ski-Out
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Set amid a mountain haven, Bentley Brook Ski Oasis delivers an unmatched winter sanctuary. With seamless ski access, thi ...
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Expedia
From $463 per night (USD)
VRBO
Cozy Lakeside Cottage Oasis
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Welcome to our charming lakeside cottage on Brewer Pond, the tranquil extension of Lake Garfield, with a neighboring sta ...
From $463 per night (USD)
VRBO
From $473 per night (USD)
Expedia
Lovely Home for Your Berkshires Trip, Clark Museum or MASS MoCA Visit
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Discover the Ultimate Berkshires Retreat: The Berkshire Apple House 🌟 Luxurious Comfort in the Heart of Berkshires Ne ...
From $473 per night (USD)
Expedia
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VRBO
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Bentley Brook Resort stands as a winter haven, providing unmatched ski-in, ski-out grandeur. Immerse yourself in the enc ...
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VRBO
From $404 per night (USD)
Expedia
The Blue Elm - A Historic Berkshire Cottage
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Welcome to The Blue Elm - a cozy and historic Berkshire getaway located in Ashley Falls, MA. Set on 3.5 tranquil acres, ...
From $404 per night (USD)
Expedia
From $210 per night (USD)
VRBO
Remodeled Unit #2, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled in history and nature, The Historic Kellogg House, built in 1739, is the third oldest house in the Berkshires. R ...
From $210 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Beautiful Renovated Home, Close to Multiple Ski Mountains.
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Great, recently renovated Berkshire Escape. Set on 6 acres with plenty of outdoor space and trails to enjoy in the warme ...
From $339 per night (USD)
Expedia
From $237 per night (USD)
VRBO
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: You want to pop out of bed, walk downstairs, and be right on the mountain - this is the place for you. This 1B ...
From $237 per night (USD)
VRBO
From $851 per night (USD)
Expedia
Sunsets On Blue Hill, Newly Renovated Farmhouse
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Summary: Welcome to Great Barrington! The heartbeat of the Berkshires! This newly remodeled home is conveniently locate ...
From $851 per night (USD)
Expedia
$Great Barrington Lakeside Getaway w\/ Kayak & Grill$
From $358 per night (USD)
VRBO
Great Barrington Lakeside Getaway w\/ Kayak & Grill
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Enjoy stunning water views and lakeside fun at this 4-bedroom + den, 4-bath vacation rental in the Berkshires. A mixture ...
From $358 per night (USD)
VRBO
$Monterey Home w\/ Hot Tub, Pool & Game Room!$
From $1654 per night (USD)
Expedia
Monterey Home w\/ Hot Tub, Pool & Game Room!
Bedrooms:
6
Bathrooms:
9
Sleeps:
16
Gather up your friends and family for the ultimate group getaway at this Monterey vacation rental! The home has nearly 4 ...
From $1654 per night (USD)
Expedia
$Jiminy Premier Ski-In\/Ski-Out Resort Bentley B$
From $472 per night (USD)
VRBO
Jiminy Premier Ski-In\/Ski-Out Resort Bentley B
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to the enchanting world of Wyndham Bentley Brook, an exclusive ski-in/ski-out retreat cradled in the breathtakin ...
From $472 per night (USD)
VRBO
$Chambery Inn \/ 7,000 Sqft Luxury Historic Berkshire landmark on Main Street$
From $6367 per night (USD)
Expedia
Chambery Inn \/ 7,000 Sqft Luxury Historic Berkshire landmark on Main Street
Bedrooms:
10
Bathrooms:
9
Sleeps:
24
***Location, Location, Location!*** The Berkshires is world-renowned for its natural beauty, artistic heritage, and c ...
From $6367 per night (USD)
Expedia
$Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In\/Ski-Out Bliss$
From $613 per night (USD)
VRBO
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In\/Ski-Out Bliss
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Embark on an Alpine Odyssey at Bentley Brook Ski-In/Ski-Out Resort, a haven for both seasoned skiers and first-time adve ...
From $613 per night (USD)
VRBO
From $1466 per night (USD)
Expedia
Forget-Me-Not by AvantStay | Bold Lakefront Escape
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Bold, modern design perched right above the shores of Lake Garfield. Forget-Me-Not is a vast, three-story Berkshires ret ...
From $1466 per night (USD)
Expedia
From $628 per night (USD)
VRBO
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Experience the beauty of the Berkshires from Cordelia, your charming Massachusetts home with a chic cottage style and ro ...
From $628 per night (USD)
VRBO
$Ski-In\/Ski-Out Bliss: Bentley Brook Resort\ ⛷️🏔️✨ #SlopeSideLuxury\n\n\n\n\n\n$
From $329 per night (USD)
Expedia
Ski-In\/Ski-Out Bliss: Bentley Brook Resort\" ⛷️🏔️✨ #SlopeSideLuxury\n\n\n\n\n\n
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Whether you're a seasoned skier or a first-time adventurer, our resort caters to all, providing access to pristine slope ...
From $329 per night (USD)
Expedia
From $126 per night (USD)
VRBO
Private Guest Suite in 1771 Farmhouse - 5 minutes to Jiminy Peak
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience the best of the Berkshires in this cozy guest suite on a circa 1771 farm. Originally a summer kitchen and sto ...
From $126 per night (USD)
VRBO
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Expedia
Mountain Lodge Apt!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A full kitchen, sofa bed and flat-screen cable TV are included in each guest room. The private bathrooms are equipped wi ...
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Expedia
From $567 per night (USD)
VRBO
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This hotel/resort is at the base of the ski lift for Jiminy Mountain. And, when you are not on the slopes, it features a ...
From $567 per night (USD)
VRBO
From $243 per night (USD)
VRBO
Light-filled Carpenter's Cottage in Stockbridge
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This adorable wooden cottage feels bright, open, and spacious. It has modern amenities alongside its rustic charm. While ...
From $243 per night (USD)
VRBO
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VRBO
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Bentley Brook Resort offers an unparalleled getaway at the base of Jiminy Peak. Nestled in the picturesque Berkshires, ...
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VRBO
$Berkshire Ski House on Lake Garfield w\/HT By Great Barrington$
From $1013 per night (USD)
Expedia
Berkshire Ski House on Lake Garfield w\/HT By Great Barrington
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Location and Design - Newly renovated by the owners, Interior Designer & Architect, 5 min from Butternut Ski mountain a ...
From $1013 per night (USD)
Expedia
From $856 per night (USD)
VRBO
Summertime at Left Bank Lodge
Bedrooms:
3
Bathrooms:
4
Sleeps:
13
Welcome to the Berkshires and all that Jiminy Peak Mountain Resort has to offer. This spacious townhome has all that you ...
From $856 per night (USD)
VRBO
From $759 per night (USD)
Expedia
Renovated 9-BR 1800s Inn 8-Min to Catamount
Bedrooms:
9
Bathrooms:
9
Sleeps:
18
Summary: Enjoy the tranquility and history of the Berkshires in this 9-bedroom, renovated 1800s inn. Property features b ...
From $759 per night (USD)
Expedia
From $307 per night (USD)
VRBO
Fabulous In-town Stockbridge Pied-á-Terre, pet friendly!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Light filled brand new stand alone home steps from quintessential Main Street Stockbridge. Large open great room, 2nd f ...
From $307 per night (USD)
VRBO
From $889 per night (USD)
Expedia
2 Bedroom Deluxe Condo, Sleeps 8, Jiminy Peak Mountain Skiing, at Bentley Brook!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This spacious two-bedroom resort suite measures approximately 843 to 953 square feet. You will enjoy a king bed in the m ...
From $889 per night (USD)
Expedia
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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 & ...
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VRBO
From $190 per night (USD)
Expedia
Mountainside Condo Ski In Ski Out
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled in the Berkshires, a getaway to Jiminy Peak offers everything you need, so close to home. Just a short walk back ...
From $190 per night (USD)
Expedia
From $402 per night (USD)
VRBO
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience the breathtaking views of Mt. Everett from one of the oldest homes in the Berkshires. Our meticulously mainta ...
From $402 per night (USD)
VRBO
From $466 per night (USD)
VRBO
Ski Relax Enjoy the Berkshires! Sparkling, New, Open and Spacious!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Sparkling, New, Open and Spacious! Beautiful Country Colonial has the charm of a traditional New England home paired wit ...
From $466 per night (USD)
VRBO
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VRBO
Cozy house Beam
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
Spacious, Cozy 1838 Post & Beam Home located within walking distance to West Stockbridge Village. Two bedrooms with poss ...
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VRBO
From $401 per night (USD)
Expedia
Luxe Log Cabin Minutes From Skiing, Hiking, & More
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Escape to the Berkshires in our newly-restored, cozy-luxe cabin, complete with fireplace, fully-stocked kitchen, high-sp ...
From $401 per night (USD)
Expedia
From $613 per night (USD)
VRBO
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
At the base of Jiminy Peak Ski Mountain, an exceptional choice for mountainside play with access to ski lifts and equipm ...
From $613 per night (USD)
VRBO
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Expedia
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
A stay at Bentley Brook Resort is a cozy, mountain retreat. Enjoy ski-in, ski-out access, spacious accommodations, and o ...
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Expedia
From $4021 per night (USD)
VRBO
Magical Country Retreat in the Berkshires, 10min from ski slopes.
Bedrooms:
10
Bathrooms:
10
Sleeps:
16
A breathtaking estate nestled on a mountain slope of granite in the Berkshires. Immerse yourself in 120 acres of natural ...
From $4021 per night (USD)
VRBO
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Expedia
Beautiful Berkshires Colonial on 7 acres
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Maison Berkshires, a nature immersion! This beautiful historic house and red barn are nestled on 7 wooded acr ...
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Expedia
$Woodland Haven w\/ Heated Pool by Evergreen Home$
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VRBO
Woodland Haven w\/ Heated Pool by Evergreen Home
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
Recently renovated, this gorgeous 2BR-3BA home features vaulted ceilings, beautiful wood beams, gorgeous stone fireplace ...
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VRBO
From $273 per night (USD)
Expedia
Guest House Sanctuary by Evergreen Home
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Beautiful haven in the woods. The 2BR guest house is currently available for up to 5 guests. Surrounded by nature, this ...
From $273 per night (USD)
Expedia
$Berkshires Estate w\/ Heated Pool by Evergreen Home$
From $1326 per night (USD)
VRBO
Berkshires Estate w\/ Heated Pool by Evergreen Home
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Welcome to your own private Berkshires paradise. Located 10 min from downtown Great Barrington or Stockbridge, and 20 mi ...
From $1326 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Located in Lanesborough, guests love this Cozy Cottage aka “Polly’s Place” for its warmth, central location and accessib ...
From $385 per night (USD)
Expedia
From $388 per night (USD)
VRBO
Cheever Hollow Farm an essential retreat central to Lenox and the Berkshires
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Welcome to Cheeverhollowfarm in picturesque Richmond/Lenox. Please Contact me for specific details or requests. We are ...
From $388 per night (USD)
VRBO
From $207 per night (USD)
Expedia
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!
Bedrooms:
1
Bathrooms:
4
Sleeps:
5
Fenced Backyard | 4 Mi to Downtown Pittsfield | Near Trails & Lakes Experience the natural beauty of the Berkshires whe ...
From $207 per night (USD)
Expedia
From $221 per night (USD)
VRBO
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Bedrooms:
2
Bathrooms:
1
Sleeps:
3
Welcome to the Mt. Williams Retreat—a centrally located guesthouse just two blocks from Williams College. Designed for g ...
From $221 per night (USD)
VRBO
From $340 per night (USD)
Expedia
Berkshire Blue House - sleeps 6!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Berkshire getaway! This 3-bedroom house sleeps 6. It has 2 bathrooms and a large deck. Two of the spacious bedrooms h ...
From $340 per night (USD)
Expedia
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Expedia
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in the wooded hills of the Berkshire Mountains, this outdoor-oriented resort offers year-round fun. Miles of be ...
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Expedia
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Expedia
Cozy 1-bedroom at a New England style resort in the Berkshire mountains
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This amazing 1-bedroom resort in Hancock is perfect for your mountain escape. With a king bed, fireplace, a convenient s ...
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Expedia
From $798 per night (USD)
VRBO
Fabulous modern home with pool & separate guest house . Pet-friendly!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Sunny modern home with separate luxury guest house. 3 lovely bedrooms in main house, 2 with en-suite bathrooms, tasteful ...
From $798 per night (USD)
VRBO
$Berkshires Lakefront Retreat\n$
From $618 per night (USD)
Expedia
Berkshires Lakefront Retreat\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Catch your breath…and let nature take it away again... Private and serene, our beautiful lakefront home is your idylli ...
From $618 per night (USD)
Expedia
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VRBO
Charming Victorian walking distance to Mass MoCa
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The Heron is a spacious 4 bedroom home with 2 full baths and a small, private, fenced-in yard. It was fully redesigned i ...
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VRBO
From $291 per night (USD)
Expedia
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Welcome to your mountain retreat, perfectly situated in Hancock's premier ski resort, Jiminy Peak. This beautifully appo ...
From $291 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Spacious Farmhouse with Stunning Views
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
The Eugene House was built in 1940 on the grounds of Abby Lodge farm, a historic summer estate across from Herman Melvil ...
From $436 per night (USD)
VRBO
From $643 per night (USD)
Expedia
New Home - Heart of Williamstown 183
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Your Dream Home in Williamstown, MA! Nestled in the heart of picturesque Williamstown, this brand-new, modern ...
From $643 per night (USD)
Expedia
From $348 per night (USD)
VRBO
Club Wyndham Bentley Brook Resort - 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
*** Sanitation/Cleaning Update *** Wyndham resorts have always met the highest standards of cleanliness, and now we are ...
From $348 per night (USD)
VRBO
From $263 per night (USD)
Expedia
Peaceful Mountain Cabin in the Berkshires
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
ENJOY A MOUNTAIN ADVENTURE! You will fall in love with this magic cottage nestled within 2 acres of old growth forest. B ...
From $263 per night (USD)
Expedia
$Pretty Farmhouse 4 bed\/3.5 ba with Gorgeous Kitchen and Big Porch - close to GB!$
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VRBO
Pretty Farmhouse 4 bed\/3.5 ba with Gorgeous Kitchen and Big Porch - close to GB!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This house is perfect for family getaways. The gourmet kitchen boasts a *gorgeous* 4-oven AGA, the king of British count ...
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VRBO
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Expedia
Beautiful 2 Bedroom in the Berkshires at Oak N Spruce Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2-bedroom villa in The Berkshires, Massachusetts! This unit is located in the perfect position for day trips to Albany, ...
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Expedia
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VRBO
Berkshire Mountain Lodge
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Berkshire Mountain Lodge The Berkshires is a cultural art haven that is home to attractions like American author Edith W ...
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VRBO
From $98 per night (USD)
Expedia
family friendly retreat condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to this adorable apartment in Pittsfield. This cozy space features 1 bedroom with a comfortable queen bed, a ful ...
From $98 per night (USD)
Expedia
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VRBO
Club Wyndham Bentley Brook Resort - 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
*** Sanitation/Cleaning Update *** Wyndham resorts have always met the highest standards of cleanliness, and now we are ...
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VRBO
From $261 per night (USD)
Expedia
Artistic Nature Cottage
Bedrooms:
2
Bathrooms:
1
Sleeps:
5
Kalarama Cottage is a newly renovated space in the middle of nature! Make yourself right at home at this quiet, private ...
From $261 per night (USD)
Expedia
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VRBO
Light-filled Carpenter's Cottage in Stockbridge
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This adorable wooden cottage feels bright, open, and spacious. It has modern amenities alongside its rustic charm. While ...
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VRBO
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Expedia
Modern Dairy Barn with Ample Natural Light and 2 Living Rooms!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to our home – where the sprawling layout of a former dairy barn is elevated through tasteful modern design. Equ ...
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Expedia
From $223 per night (USD)
VRBO
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Come and spend a weekend relaxing by a fire or exploring the many restaurants and outdoor activities from this unique an ...
From $223 per night (USD)
VRBO
From $655 per night (USD)
Expedia
Contemporary 3-bedroom home with views, fireplace & close to Butternut Ski area
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Guests can take in the view from the front porch, and the house has plenty of space, including the basement game room an ...
From $655 per night (USD)
Expedia
From $274 per night (USD)
VRBO
Great Place - 2 BD - Kitchen - Pool 
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick ...
From $274 per night (USD)
VRBO
From $274 per night (USD)
Expedia
Great Place - 2 BD - Kitchen and Pool 
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick ...
From $274 per night (USD)
Expedia
$Berkshire Summer Retreat - 3 bed\/2 bath$
From $347 per night (USD)
VRBO
Berkshire Summer Retreat - 3 bed\/2 bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Perfect Berkshire getaway. Minutes from downtown Great Barrington and Stockbridge, Tanglewood, Rockwell Museum, multipl ...
From $347 per night (USD)
VRBO
From $852 per night (USD)
Expedia
Ray of Sunshine Berkshire Home on Pontoosuc Lake
Bedrooms:
5
Bathrooms:
5
Sleeps:
14
Brand new construction directly on Lake Pontoosuc. This home sleeps 14 guests. There is a brand new chef’s kitchen! Th ...
From $852 per night (USD)
Expedia
From $564 per night (USD)
VRBO
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Family or couples getaway! 3 bedrooms plus library, Sleeps 6-8 A beautiful 3050 Sq. Ft., 2-Story Colonial and attached ...
From $564 per night (USD)
VRBO
From $334 per night (USD)
Expedia
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)
Expedia
From $295 per night (USD)
VRBO
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)
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
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 $426 per night (USD)
Expedia
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)
Expedia
From $465 per night (USD)
VRBO
Designer Berkshire Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This is what ‘Tiny Home’ Dreams are made of! Our Renovated Designer Cottage located in rural Richmond Massachusetts is c ...
From $465 per night (USD)
VRBO
From $742 per night (USD)
Expedia
Lake Buel Lakefront - 4 Bedrooms with private dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Idyllic Berkshire lakeside 4 bedroom cottage offering swimming, fishing, water sports and hiking. Located directly on t ...
From $742 per night (USD)
Expedia
From $1106 per night (USD)
VRBO
Panoramic Views, Indoor Pool by Evergreen Home
Bedrooms:
5
Bathrooms:
5
Sleeps:
11
An ideal retreat nestled in the Berkshires with vast, expansive panoramic views. With 4 BR, 4.5 BA, a brand new gorgeous ...
From $1106 per night (USD)
VRBO
From $201 per night (USD)
Expedia
Stay at Beaver Lodge!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This secluded and private one-bedroom cottage has two gas stoves to keep you toasty in winter and A/C to keep you cool i ...
From $201 per night (USD)
Expedia
From $1162 per night (USD)
VRBO
The Brookman: Renovated 6000 SF Estate On 40 Acres
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
Summary: Previously owned by one of Hollywood’s most iconic actors, this 6,000 SF estate sits on 40 secluded acres with ...
From $1162 per night (USD)
VRBO
From $604 per night (USD)
Expedia
Serene Berkshires Home On 5+ Acres, Rustic & Chic
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Summary: Enjoy the beauty of the Berkshires in our tranquil retreat! The home, with rustic charm and modern touches, fea ...
From $604 per night (USD)
Expedia
$Pres day weekend! STUDIO Sleeps 4 Ski in\/out Wyndham Bentley Brook JIminy$
From $382 per night (USD)
VRBO
Pres day weekend! STUDIO Sleeps 4 Ski in\/out Wyndham Bentley Brook JIminy
Bedrooms:
1
Bathrooms:
1
Sleeps:
8
I pre-reserved President and MLK weekend Friday to Monday for your family. Luxury Room is right on Jiminy Peak's learni ...
From $382 per night (USD)
VRBO
From $519 per night (USD)
Expedia
Family Friendly in Sheffield, private yet close to everything!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Your perfect country escape. Clean, spacious, light and airy home set in the middle of a meadow on 20 acres. Complete pr ...
From $519 per night (USD)
Expedia
From $547 per night (USD)
VRBO
An In-Town Beauty with Late Checkout
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Berkshires and all its attractions are at your doorstep in this newly renovated, well-insulated 1900 Victorian, situ ...
From $547 per night (USD)
VRBO
From $1289 per night (USD)
Expedia
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)
Expedia
From $288 per night (USD)
VRBO
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)
VRBO
From $187 per night (USD)
Expedia
Summer in the BERKSHIRES!
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Spend the SUMMER in the HEART of the BERKSHIRES! JUST minutes from both the Lenox and Stockbridge Town Beach with access ...
From $187 per night (USD)
Expedia
From $464 per night (USD)
VRBO
Wyndham Bentley Brook Condo Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
8
Nestled in the Berkshire Mountains at the base of Jiminy Peak Ski Mountain, Wyndham Bentley Brook takes "weekend getaway ...
From $464 per night (USD)
VRBO
From $421 per night (USD)
Expedia
Modern Retreat on Goose Pond
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A modern 3-bedroom, 2-bathroom idyllic getaway surrounded by the Berkshires’ lush forests, mountain vistas and culture. ...
From $421 per night (USD)
Expedia

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