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 $638 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 $638 per night (USD)
VRBO
From $290 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 $290 per night (USD)
VRBO
From $477 per night (USD)
VRBO
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
Welcome to Wyndham Bentley Brook, your gateway to the ultimate ski-in, ski-out experience at the majestic Jiminy Peak! N ...
From $477 per night (USD)
VRBO
$Your Winter Escape: Wyndham Bentley Brook Ski-In, Ski-Out Bliss at Jiminy Peak!\$
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Expedia
Your Winter Escape: Wyndham Bentley Brook Ski-In, Ski-Out Bliss at Jiminy Peak!\"
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
Experience the ultimate ski-in, ski-out getaway at Wyndham Bentley Brook, nestled in the heart of the Berkshire Mountain ...
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Expedia
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
From $613 per night (USD)
Expedia
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)
Expedia
From $1002 per night (USD)
VRBO
Forget-Me-Not by AvantStay | Bold Lakefront Escape
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
★ Recognized as one of our best. This home was a finalist in the 2025 AvantStay Awards, our annual celebration of top-ti ...
From $1002 per night (USD)
VRBO
From $535 per night (USD)
Expedia
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 $535 per night (USD)
Expedia
$Ski-In/Ski-Out Bliss: Bentley Brook Resort\ ⛷️🏔️✨ #SlopeSideLuxury\n\n\n\n\n\n$
From $329 per night (USD)
VRBO
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)
VRBO
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Expedia
Fun on the slopes with pool @Vacation Village Berkshires1.0 miles to Jiminy Peak
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Bring your family at this private unit at the Vacation Village in the Berkshires. Views of the Jiminy Peak Ski Resort sl ...
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Expedia
From $494 per night (USD)
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 ...
From $494 per night (USD)
VRBO
From $614 per night (USD)
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 ...
From $614 per night (USD)
Expedia
From $455 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 $455 per night (USD)
VRBO
From $445 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 $445 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 $1085 per night (USD)
VRBO
Mountain Luxury Retreat-Amazing Views/Saltwater Pool/Family Friendly/Berkshires
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
Newly built in 2007, this home was designed with comfort, luxury and family fun in mind. The property is 12 acres in si ...
From $1085 per night (USD)
VRBO
From $404 per night (USD)
VRBO
The Blue Elm - A Historic Berkshire Cottage
Bedrooms:
1
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)
VRBO
From $170 per night (USD)
Expedia
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 $170 per night (USD)
Expedia
From $339 per night (USD)
VRBO
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)
VRBO
From $253 per night (USD)
Expedia
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
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 $253 per night (USD)
Expedia
From $650 per night (USD)
VRBO
Sunsets On Blue Hill, Newly Renovated Farmhouse
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: Welcome to Great Barrington! The heartbeat of the Berkshires! This newly remodeled home is conveniently locate ...
From $650 per night (USD)
VRBO
From $332 per night (USD)
Expedia
Great Barrington Lakeside Getaway w/ Kayak & Grill
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Enjoy stunning water views and lakeside fun at this 4-bedroom + den, 4-bath vacation rental in the Berkshires. A mixture ...
From $332 per night (USD)
Expedia
From $1057 per night (USD)
VRBO
Monterey Home w/ Hot Tub, Pool & Game Room!
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
Gather up your friends and family for the ultimate group getaway at this Monterey vacation rental! The home has nearly 4 ...
From $1057 per night (USD)
VRBO
From $270 per night (USD)
Expedia
2-Bdr Apt In Town, By the Water
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
★ New to Williamstown? Explore our interactive guidebook. A flight of steps takes you to this stunning 2BDR on the 2nd ...
From $270 per night (USD)
Expedia
From $257 per night (USD)
VRBO
New Studio In Town, By the Water
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
★ New to Williamstown? Explore our interactive guidebook. Charming studio just steps away from shops, restaurants & few ...
From $257 per night (USD)
VRBO
From $354 per night (USD)
Expedia
Stay Lakeside This Summer!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Secluded lakefront bliss, retreat in Great Barrington! Sleeps six with modern amenities, scenic views, and outd ...
From $354 per night (USD)
Expedia
From $277 per night (USD)
VRBO
Downtown | Waterfront | Walk to Shops
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
★ New to Williamstown? Explore our interactive guidebook. One bedroom with all the bells and whistles! Meticulously upg ...
From $277 per night (USD)
VRBO
From $716 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 $716 per night (USD)
Expedia
From $716 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 $716 per night (USD)
VRBO
From $594 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 $594 per night (USD)
Expedia
From $621 per night (USD)
VRBO
Prime Location and Charm – 5 Mins to Tanglewood & Best Berkshire Attractions
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Stylish Berkshires Retreat: This charming home, nestled in the heart of the Berkshires, awaits your next visit. With 4 b ...
From $621 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 $553 per night (USD)
VRBO
Berkshire House Stay
Bedrooms:
7
Bathrooms:
5
Sleeps:
10
Welcome to the Berkshires. BHS is in the center of it all. You can take a stroll to downtown Lee or a quick drive to Sto ...
From $553 per night (USD)
VRBO
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Expedia
Farmhouse on Otis Pond
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
A spacious farmhouse with room for 10 has a large porch with rocking chairs, access to the pond, large yard, fire pit. ...
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Expedia
From $257 per night (USD)
VRBO
Cozy Cottage in the Berkshires on 1.6 Acres
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to our Modern Rustic Cottage in the Berkshires! The Accommodations: Bedroom 1: A comfortable queen-sized bed. Be ...
From $257 per night (USD)
VRBO
From $659 per night (USD)
VRBO
Ray of Sunshine Berkshire Home on Pontoosuc Lake
Bedrooms:
4
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 $659 per night (USD)
VRBO
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VRBO
Cozy and large 2 Bedroom 2 Full Bath ski in, ski out condo Unit with balcony.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Family friendly resort with indoor/outdoor heated pool, 2 hot tubs, fitness gym, game room, ski/equip rentals, daily act ...
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VRBO
From $406 per night (USD)
Expedia
Lakeshore cabin with 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, next to a waterfall. Ser ...
From $406 per night (USD)
Expedia
From $373 per night (USD)
VRBO
Cozy 3BR Home w/ Yard & Patio 5 min to Tanglewood
Bedrooms:
1
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 $373 per night (USD)
VRBO
From $388 per night (USD)
Expedia
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 $388 per night (USD)
Expedia
From $444 per night (USD)
VRBO
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 $444 per night (USD)
VRBO
$Private Lake Cottage on 3 acres w/350 sq. ft. deck\n$
From $343 per night (USD)
Expedia
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 $343 per night (USD)
Expedia
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 $436 per night (USD)
Expedia
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: Nestled in the Berkshires, this 5-BR family home combines comfort and tranquility. The open floor plan connects ...
From $436 per night (USD)
Expedia
From $388 per night (USD)
VRBO
Hudson Valley and The Berkshires getaway
Bedrooms:
6
Bathrooms:
4
Sleeps:
9
Summary: Welcome to the Hudson Valley getaway. Located in the heart of the Hudson Valley in Hillsdale NY, sits our 4 be ...
From $388 per night (USD)
VRBO
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Expedia
Summer rental 4Br - Big views + Pond, 10 acres bwtn Hudson and Great Barrington
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
In the foothills of the Berkshire Mountains on a quiet country road halfway between Great Barrington (15Min) and Hudson ...
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Expedia
From $302 per night (USD)
VRBO
Hudson valley and The Berkshires Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to your luxury cottage escape. Located in the heart of the Hudson Valley in Hillsdale, NY sits a calm, ...
From $302 per night (USD)
VRBO
From $992 per night (USD)
VRBO
Luxury Retreat Minutes from Downtown Great Barrington & Ski Slopes
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to the perfect Berkshires getaway! Nestled on 10 private acres and just minutes from downtown Great Barrington, t ...
From $992 per night (USD)
VRBO
From $374 per night (USD)
VRBO
Lakeside 3-BR Berkshires Residence
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Enjoy this newly renovated 3-BR home nestled along the shores of Long Bow Lake, offering stunning views and dir ...
From $374 per night (USD)
VRBO
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Expedia
Overlooking the city in a quiet 7 unit building
Bedrooms:
2
Bathrooms:
1
Sleeps:
3
This is a quiet, 7 unit, newly renovated condominium building. We welcome quiet guests who will appreciate a relaxing st ...
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Expedia
From $245 per night (USD)
VRBO
Lakefront Cottage in the Berkshires
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
5 North Lake is a seasonal cottage situated yards from the shore. The property has panoramic views of the largest recrea ...
From $245 per night (USD)
VRBO
From $137 per night (USD)
Expedia
Entire home in Dalton, Massachusetts, United States
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. ...
From $137 per night (USD)
Expedia
From $741 per night (USD)
VRBO
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Located near Lenox, Stockbridge, and Lee, this private and peaceful country house with modern amenities offers a relaxin ...
From $741 per night (USD)
VRBO
From $780 per night (USD)
Expedia
Mountain Blossom Retreat by Evergreen Home
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This centrally located property at the base of Mount Greylock offers luxury and tranquility on 60 private acres with swe ...
From $780 per night (USD)
Expedia
From $166 per night (USD)
VRBO
Pet friendly, cozy, modest cape, two bedrooms
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
You, those in your party and your pet(s) will have this modest, quirky, cozy, cape style, home all to yourself. There ar ...
From $166 per night (USD)
VRBO
From $1040 per night (USD)
VRBO
6-BR Berkshires Estate w Pool
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
Expansive Berkshires family home situated on 4 pastoral acres. The home features post-and-beam primary with 6-BRs, lofte ...
From $1040 per night (USD)
VRBO
From $462 per night (USD)
VRBO
Tanglewood Treasure! A Gracious Retreat in the Heart of the Berkshires
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
One of TWO lovely dwellings for rent on nearly four private acres. See VRBO 3529604 to learn more about our Charming Ber ...
From $462 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A perfect stay in the Berkshires! Just 1.5 miles from downtown Great Barrington and 1 mile from Butternut Ski Area, our ...
From $304 per night (USD)
Expedia
From $578 per night (USD)
VRBO
LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Enjoy this very private, super comfortable, 1925 lake cottage, waterfront boathouse and dock for an entire Berkshire Sum ...
From $578 per night (USD)
VRBO
From $400 per night (USD)
Expedia
Waterfront Cottage 10 Min From Great Barrington
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A couple's getaway for the books awaits you at this Lake Buel vacation rental. Just 6 miles from Great Barrington's shop ...
From $400 per night (USD)
Expedia
$house with view in the berkshires\n$
From $339 per night (USD)
VRBO
house with view in the berkshires\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience the charm of this newly renovated home with a wrap-around deck with vistas of a lake and mountains. Airy ope ...
From $339 per night (USD)
VRBO
From $810 per night (USD)
VRBO
Saltbox-style residence in the Berkshires
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the allure of this enchanting Saltbox-style residence nestled in the picturesque town of Hillsdale, NY. With t ...
From $810 per night (USD)
VRBO
From $527 per night (USD)
VRBO
Elegant Mountain View Retreat By Evergreen Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Explore the best of the Berkshires at this private country retreat, minutes from the Williams campus, world-class museum ...
From $527 per night (USD)
VRBO
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Expedia
Renovated Berkshires Farmhouse - minutes from hiking, swimming, and Tanglewood
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Our airy, renovated farmhouse sits on a peaceful 8.5 acres on a quiet road, yet in close proximity to the towns of Lenox ...
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Expedia
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VRBO
Berkshire apartment on Green River; in ground pool; walking trail - pet friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to tranquility at this country home nestled among the picturesque Berkshires of Massachusetts. Located in North E ...
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VRBO
From $767 per night (USD)
Expedia
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Great Barrington 3BR / 3BA retreat nestled on 4.7 acres of park-like grounds. Relax in the inviting hot tub under the st ...
From $767 per night (USD)
Expedia
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VRBO
Spectacular views and close to Great Barrington.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Main floor bedroom with private bath, 2 car garage, electric vehicle charging, screened porch, pool, and Koi pond with v ...
Click For Pricing
VRBO
From $396 per night (USD)
VRBO
Light-filled family home. Book now for the summer!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Light-filled modern 4 bedroom, 3.5 bath home in the Berkshires. This lovely two story home features a master bedroom on ...
From $396 per night (USD)
VRBO
From $221 per night (USD)
VRBO
Gateway to the Berkshires - Renovated downtown apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Completely renovated downtown second floor apartment with open floor plan, located in historical downtown Lee. This apar ...
From $221 per night (USD)
VRBO
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Expedia
Adorable Berkshires Loft on Quiet Dirt Road. Close to Tanglewood.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sweet loft on quiet dirt road. First floor has kitchen, eating area, living room, bathroom with laundry, three season p ...
Click For Pricing
Expedia
From $298 per night (USD)
VRBO
Quiet 3BR Home, Near Tanglewood in Stockbridge
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Modern family home moments from Tanglewood, the Stockbridge Bowl, the Norman Rockwell and Chesterwood Museums. Just a 10 ...
From $298 per night (USD)
VRBO
From $446 per night (USD)
VRBO
Luxury Cabin Fall Views & Deck besides Kennedy Park, Walk to Lenox.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Elegant, light-filled cabin blending modern comfort with rustic charm, nestled beside Kennedy Park. Enjoy mesmerizing ...
From $446 per night (USD)
VRBO
From $558 per night (USD)
VRBO
18th century Berkshires farmhouse on 12 acres, impeccably updated.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Woods, stone walls, a wet bar, a swimming pool with chaise lounges, a wood burning stove, all 15-ish minutes from Great ...
From $558 per night (USD)
VRBO
From $524 per night (USD)
Expedia
Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Introducing Woodland Zen: where modern luxury meets secluded tranquility in the heart of the Berkshires. This sleek, co ...
From $524 per night (USD)
Expedia
From $1942 per night (USD)
VRBO
***Your Own B&B*** Su
Bedrooms:
12
Bathrooms:
13
Sleeps:
36
Summary: **Please message us prior to booking and talking with your group to confirm pricing and availability** Interio ...
From $1942 per night (USD)
VRBO
From $387 per night (USD)
Expedia
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
720 Sq. Ft, 2 Bed, 1 Bath cottage with HOT TUB amongst the forest located in a private, dirt road, lake community with n ...
From $387 per night (USD)
Expedia
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VRBO
Spacious 4 bedroom, big pool & outdoor space. Close for local summer activities!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Less than 2 miles from Williams College, this a great homebase for the upcoming Williams events or other summer events i ...
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VRBO
From $263 per night (USD)
Expedia
Luxury 2 Bedroom 2 Bathroom Loft Apartment In Williamstown With Great Amenities!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Luxury two-bedroom loft apartment for in the prestigious Cable Mills building in Williamstown, Massachusetts. A five-min ...
From $263 per night (USD)
Expedia
From $150 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $150 per night (USD)
VRBO
From $150 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $150 per night (USD)
VRBO
From $150 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $150 per night (USD)
VRBO
From $150 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $150 per night (USD)
VRBO
From $274 per night (USD)
VRBO
Golf House by Mt Greylock - Walkable Adventures!
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Relax in our spacious 4-bedroom, 3-bath home, nestled at the end of a quiet dead-end road with a large yard and cozy spo ...
From $274 per night (USD)
VRBO
From $274 per night (USD)
Expedia
Stylish Newly Renovated 2-Bedroom Apartment Steps from Otis Reservoir
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our stylish, newly renovated 2-bedroom apartment, just steps from the beautiful Otis Reservoir! Located only ...
From $274 per night (USD)
Expedia
$Berkshires Lakefront Gem. Cozy home w/ hiking, swimming & all things cultural!\n$
From $315 per night (USD)
VRBO
Berkshires Lakefront Gem. Cozy home w/ hiking, swimming & all things cultural!\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The perfect getaway for people who want to unwind from the grind of everyday life. Little Robin Lake is located right in ...
From $315 per night (USD)
VRBO
Click For Pricing
Expedia
Bygone era Lake Buel cottage with access to shared dock and canoe
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Re-introducing a wonderful cottage built in the early 1900’s, one of the first privately owned constructions near the la ...
Click For Pricing
Expedia
From $268 per night (USD)
VRBO
Luxury on the River@Fish Camp-Close to Tanglewood
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Relax with the entire family in this beautiful new home built on the Farmington River. Enjoy luxurious, natural open spa ...
From $268 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Berkshires' best! Tanglewood, Jacob's Pillow and 400 feet from a pristine lake
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This newly renovated house in the woods on a private road in Lee is an ideal summer or fall retreat. Our little communit ...
From $321 per night (USD)
Expedia
From $447 per night (USD)
VRBO
Baldwin Hill Retreat Guest House
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
In one of the most sought after destinations in New England, located just outside Great Barrington near the top of Baldw ...
From $447 per night (USD)
VRBO
From $722 per night (USD)
VRBO
Berkshires Summer Chalet w/ Pool + Private Hiking Trails
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Nestled in the foothills of East Mountain, just minutes from the center of Great Barrington, this woodsy pine cabin has ...
From $722 per night (USD)
VRBO
From $172 per night (USD)
VRBO
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in history and nature, The Historic Kellogg House, built in 1739, is the third oldest house in the Berkshires. R ...
From $172 per night (USD)
VRBO
From $344 per night (USD)
VRBO
Delightful Stockbridge House, Walk to Town!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Within walking distance to Main Street in Stockbridge, 38 Church St. offers a large backyard and gardens which boarder p ...
From $344 per night (USD)
VRBO
From $485 per night (USD)
VRBO
Sophisticated and secluded Lenox Mt retreat minutes from Tanglewood. New listing
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this chic Lenox Mountain chalet in picturesque West Stockbridge, just minutes from Tanglewood. In a secluded w ...
From $485 per night (USD)
VRBO
From $114 per night (USD)
VRBO
1br Deluxe Condo Jiminy Peak Skiing!
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $114 per night (USD)
VRBO
From $114 per night (USD)
VRBO
1br Deluxe Condo Jiminy Peak Skiing!
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $114 per night (USD)
VRBO
From $105 per night (USD)
VRBO
Studio Condo Outdoor Adventures
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $105 per night (USD)
VRBO
From $105 per night (USD)
VRBO
Studio Condo Outdoor Adventures
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $105 per night (USD)
VRBO
From $114 per night (USD)
VRBO
1br Deluxe Condo Jiminy Peak Skiing!
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $114 per night (USD)
VRBO
From $105 per night (USD)
VRBO
Studio Condo Outdoor Adventures
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $105 per night (USD)
VRBO
From $105 per night (USD)
VRBO
Studio Condo Outdoor Adventures
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $105 per night (USD)
VRBO

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