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 $604 per night (USD)
VRBO
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 $604 per night (USD)
VRBO
From $340 per night (USD)
Expedia
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Stay at the heart of it all. Walk to lifts, restaurants, shopping and amenities right from your door. It doesn’t get an ...
From $340 per night (USD)
Expedia
From $299 per night (USD)
VRBO
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This ski-in, ski-out loft is located right at the base of the mountain in the Thatcher Lodge in the heart of the village ...
From $299 per night (USD)
VRBO
From $998 per night (USD)
VRBO
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
Bedrooms:
4
Bathrooms:
5
Sleeps:
11
Renovations just finished on this unique home, that originally dates to the 1700s. Great for families and big groups, wi ...
From $998 per night (USD)
VRBO
From $345 per night (USD)
VRBO
Park Street Penthouse Apartment
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Stay in one of the best preserved historical home that's now a private art galley in downtown Adams. Walk to Adams Thea ...
From $345 per night (USD)
VRBO
From $396 per night (USD)
Expedia
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Wake up to spectacular sunrise lake views from the deck or while soaking in the hot tub. Close to all the year round a ...
From $396 per night (USD)
Expedia
$Stockbridge Retreat w\/ Pool & Hot Tub!$
From $1547 per night (USD)
VRBO
Stockbridge Retreat w\/ Pool & Hot Tub!
Bedrooms:
4
Bathrooms:
8
Sleeps:
10
Escape to the Berkshires and indulge in the ultimate experience at this luxurious 4-bedroom, 3.5-bathroom house. Situate ...
From $1547 per night (USD)
VRBO
From $549 per night (USD)
Expedia
Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
**20% Discount for month-long stays/ 10% discount for week stays automatically applied**. *Inquire: Seasonal rental disc ...
From $549 per night (USD)
Expedia
$Serene Berkshires Cabin w\/ Deck & Fire Pit!$
From $366 per night (USD)
VRBO
Serene Berkshires Cabin w\/ Deck & Fire Pit!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Discover the charm, beauty, and fun of the Berkshires from this 4-bedroom, 3-bath Otis cabin. Featuring a peaceful woode ...
From $366 per night (USD)
VRBO
Click For Pricing
Expedia
Serene Acreage - Pond - Hiking Trails Nearby
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hawks Eye Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For Pricing
Expedia
From $144 per night (USD)
VRBO
Wyndham Bentley Brook! 2 Bd. dlx. in Hancock
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Everyone needs a place to lay their weary head. For travelers visiting Hancock, Wyndham at Bentley Brook is an excellent ...
From $144 per night (USD)
VRBO
From $622 per night (USD)
Expedia
Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Autumn Hill Lakehouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $622 per night (USD)
Expedia
From $144 per night (USD)
VRBO
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Everyone needs a place to lay their weary head. For travelers visiting Hancock, Wyndham at Bentley Brook is an excellent ...
From $144 per night (USD)
VRBO
$Monterey Haven < 1\/2 Mi to Lake Garfield w\/ Kayaks$
From $349 per night (USD)
Expedia
Monterey Haven < 1\/2 Mi to Lake Garfield w\/ Kayaks
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Get carried away to this quaint 3-bedroom, 1-bath vacation rental in beautiful Monterey, Massachusetts. Surrounded by sc ...
From $349 per night (USD)
Expedia
Click For Pricing
VRBO
Large Country farmhouse in the Berkshires.
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Welcome to Brookside Farm, a 5000sqft one level farmhouse on 70 acres of woodlands and fields with a large pond that yie ...
Click For Pricing
VRBO
From $439 per night (USD)
Expedia
A cozy home nestled in the Green Mountains of Vermont!
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Our cozy home is great in all seasons! Comfortably furnished, it is a great place to read in front of the fire, set out ...
From $439 per night (USD)
Expedia
$Romantic Boutique Hotel \/ Bed and Breakfast - Standard Queen Handicap Accessible$
From $1276 per night (USD)
VRBO
Romantic Boutique Hotel \/ Bed and Breakfast - Standard Queen Handicap Accessible
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A traditional room with great charm, L'Atelier is completely handicapped accessible. This room, with its queen-sized bed ...
From $1276 per night (USD)
VRBO
$2 Bedroom Deluxe Condo w\/ Kitchen at Bentley Brook, Jiminy Peak Ski Mountain!!$
From $840 per night (USD)
VRBO
2 Bedroom Deluxe Condo w\/ Kitchen at Bentley Brook, Jiminy Peak Ski Mountain!!
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 $840 per night (USD)
VRBO
From $373 per night (USD)
VRBO
Shales Brook Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Shales Brook Cottage is a newly renovated 2 bedroom and 2 bath, fantastic place. Vintage Malm wood burning stove for coo ...
From $373 per night (USD)
VRBO
From $144 per night (USD)
Expedia
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Everyone needs a place to lay their weary head. For travelers visiting Hancock, Wyndham at Bentley Brook is an excellent ...
From $144 per night (USD)
Expedia
$Gorgeous Mountain View Suite Ski On\/Off At Jiminy - Fully Redone Decor$
From $227 per night (USD)
VRBO
Gorgeous Mountain View Suite Ski On\/Off At Jiminy - Fully Redone Decor
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to modern country comfort. This unique Suite lies right on Jiminy Peak Mountain within the Country Inn ...
From $227 per night (USD)
VRBO
From $238 per night (USD)
Expedia
Private Cabin On Over 12 Acres Of Woods!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: This home features both modern finishes & New England charm. Large open great room, chef's kitchen & brick fire ...
From $238 per night (USD)
Expedia
From $1385 per night (USD)
VRBO
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
In one of the most sought after destinations in New England, located just outside Great Barrington near the top of Baldw ...
From $1385 per night (USD)
VRBO
From $465 per night (USD)
VRBO
Secret, one-bedroom hideaway overlooking picturesque field in Williamstown
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Looking for a private escape in the Berkshires? Come visit our brand new, one-bedroom/one-bathroom, well equipped first- ...
From $465 per night (USD)
VRBO
From $510 per night (USD)
VRBO
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 $510 per night (USD)
VRBO
Click For Pricing
Expedia
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 & ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Quaint Single Story 1Bd with Vintage Charm, Walk to Downtown Restaurants & Shops
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to our charming 1 bedroom, 1 bath single-level duplex, located just 2 town blocks from the heart of downtown Lee ...
Click For Pricing
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $188 per night (USD)
VRBO
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 $188 per night (USD)
VRBO
From $479 per night (USD)
Expedia
Charming historic farmhouse minutes to Great Barrington MA and Salisbury CT
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Update 5/31: We are new to VRBO and are thrilled with the feedback we have had from our guests thus far. You will love s ...
From $479 per night (USD)
Expedia
From $456 per night (USD)
VRBO
Rest 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 $456 per night (USD)
VRBO
From $768 per night (USD)
Expedia
Stunning 6-BR Country Home 10-min to Catamount
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Summary: Escape to the highlands of the Berkshires on this peaceful, 4-acre lot 10-min to skiing at Catamount and 10-min ...
From $768 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $3774 per night (USD)
VRBO
Magical Country Retreat in the Berkshires
Bedrooms:
9
Bathrooms:
9
Sleeps:
16
A breathtaking estate nestled on a mountain slope of granite in the Berkshires. Immerse yourself in 120 acres of natural ...
From $3774 per night (USD)
VRBO
$Ski Jiminy Peak Xmas wk Sun-Wed 3 nites; Ski In\/Ski Out @Wyndham Bentley Brook$
Click For Pricing
Expedia
Ski Jiminy Peak Xmas wk Sun-Wed 3 nites; Ski In\/Ski Out @Wyndham Bentley Brook
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Wyndham Bentley Brook - Delux 2 Bedrm/2 Bathrm fully equipped Condo. Master Bdrm has K bed with shwr & jacuzzi, while 2n ...
Click For Pricing
Expedia
From $603 per night (USD)
Expedia
Slope-Side Ski-in Ski-Out: Bentley Brook Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Wyndham Bentley Brook, a premier ski-in, ski-out resort, offers the ultimate winter escape. Enjoy the slopes and cozy ac ...
From $603 per night (USD)
Expedia
From $378 per night (USD)
VRBO
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 ...
From $378 per night (USD)
VRBO
$Berkshires Estate w\/ Heated Pool by Evergreen Home$
From $1084 per night (USD)
Expedia
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, 5 min fro ...
From $1084 per night (USD)
Expedia
From $419 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 $419 per night (USD)
VRBO
From $214 per night (USD)
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 ...
From $214 per night (USD)
Expedia
From $465 per night (USD)
VRBO
Lakeside Retreat Just You, The Lake & The View!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Summary: Secluded lakefront bliss, retreat in Great Barrington! Sleeps six with modern amenities, scenic views, and outd ...
From $465 per night (USD)
VRBO
From $749 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 $749 per night (USD)
Expedia
From $749 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 $749 per night (USD)
VRBO
From $546 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 $546 per night (USD)
Expedia
From $372 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 $372 per night (USD)
VRBO
$Bentley Brook Alpine Haven: Premier Ski-In\/Ski-Out$
From $488 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 $488 per night (USD)
Expedia
From $455 per night (USD)
VRBO
Cozy Lakeside Cottage Oasis
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
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 $438 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 $438 per night (USD)
Expedia
From $603 per night (USD)
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 ...
From $603 per night (USD)
VRBO
From $416 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 $416 per night (USD)
Expedia
From $159 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 $159 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 $227 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 $227 per night (USD)
VRBO
From $554 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 $554 per night (USD)
Expedia
$Great Barrington Lakeside Getaway w\/ Kayak & Grill$
From $339 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 $339 per night (USD)
VRBO
$Monterey Home w\/ Hot Tub, Pool & Game Room!$
From $1329 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 $1329 per night (USD)
Expedia
$Bentley Brook: Elevate Your Winter Thrills with Premier Ski-In\/Ski-Out Luxury$
From $416 per night (USD)
VRBO
Bentley Brook: Elevate Your Winter Thrills with Premier Ski-In\/Ski-Out Luxury
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 $416 per night (USD)
VRBO
$Chambery Inn \/ 7,000 Sqft Luxury Historic Berkshire landmark on Main Street$
From $2558 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 $2558 per night (USD)
Expedia
$Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In\/Ski-Out Bliss$
From $390 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 $390 per night (USD)
VRBO
From $999 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 $999 per night (USD)
Expedia
From $478 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 $478 per night (USD)
VRBO
$Ski-In\/Ski-Out Bliss: Bentley Brook Resort\ ⛷️🏔️✨ #SlopeSideLuxury\n\n\n\n\n\n$
From $449 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 $449 per night (USD)
Expedia
From $124 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 $124 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $537 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 $537 per night (USD)
VRBO
From $221 per night (USD)
VRBO
Light-filled Carpenter's Cottage - 2 mi. north of downtown 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 $221 per night (USD)
VRBO
From $488 per night (USD)
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, ...
From $488 per night (USD)
VRBO
$Berkshire Ski House on Lake Garfield w\/HT By Great Barrington$
From $838 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 $838 per night (USD)
Expedia
$Ski-In\/Ski-Out at Left Bank Lodge$
From $859 per night (USD)
VRBO
Ski-In\/Ski-Out 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 $859 per night (USD)
VRBO
From $144 per night (USD)
Expedia
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Everyone needs a place to lay their weary head. For travelers visiting Hancock, Wyndham at Bentley Brook is an excellent ...
From $144 per night (USD)
Expedia
From $144 per night (USD)
VRBO
Outside Adventure-Skiing, Hiking, and Relaxation
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Everyone needs a place to lay their weary head. For travelers visiting Hancock, Wyndham at Bentley Brook is an excellent ...
From $144 per night (USD)
VRBO
From $763 per night (USD)
Expedia
Renovated 9-BR 1800s Inn 8-Min to Catamount
Bedrooms:
8
Bathrooms:
9
Sleeps:
18
Summary: Enjoy the tranquility and history of the Berkshires in this 9-bedroom, renovated 1800s inn. Property features b ...
From $763 per night (USD)
Expedia
From $289 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 $289 per night (USD)
VRBO
From $800 per night (USD)
Expedia
Beautiful Berkshires Cottage on Lake Buel
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Slow down and appreciate the simple pleasures of lakeside living at this peaceful 3-bedroom, 2.5-bathroom vacation renta ...
From $800 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
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. ...
Click For Pricing
VRBO
From $273 per night (USD)
Expedia
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 $273 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $327 per night (USD)
Expedia
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 $327 per night (USD)
Expedia
$Cozy 3BR Home w\/ Yard & Patio 5 min to Tanglewood$
From $408 per night (USD)
VRBO
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 $408 per night (USD)
VRBO
$4BR Home w\/ Yard & BBQ, 5 min walk to downtown Lee$
Click For Pricing
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 ...
Click For Pricing
Expedia
$Colonial House, w\/Yard,7min walk to Downtown Lenox$
From $267 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 $267 per night (USD)
VRBO
$Private Lake Cottage on 3 acres w\/350 sq. ft. deck\n$
From $272 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 $272 per night (USD)
Expedia
$Berkshires sanctuary w\/ outdoor living area & fire pit. Minutes from Tanglewood!$
From $676 per night (USD)
VRBO
Berkshires sanctuary w\/ outdoor living area & fire pit. Minutes from Tanglewood!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Located near Lenox, Stockbridge, and Lee, this private and peaceful country house with modern amenities offers a relaxin ...
From $676 per night (USD)
VRBO
$Serene Berkshires Oasis w\/ Pool & Sculpture Garden$
Click For Pricing
Expedia
Serene Berkshires Oasis w\/ Pool & Sculpture Garden
Bedrooms:
4
Bathrooms:
6
Sleeps:
8
Unwind with loved ones at this one-of-a-kind vacation rental in Otis, Massachusetts! Boasting 3 bedrooms, 3.5 bathrooms, ...
Click For Pricing
Expedia
From $735 per night (USD)
VRBO
Mountain Blossom Retreat by Evergreen Home
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This centrally located property at the base of Mount Greylock offers luxury and tranquility on 60 private acres with swe ...
From $735 per night (USD)
VRBO
$\nCharming 3-bedroom townhome owned by artist in wonderful Lenox with WiFi, AC.\n$
From $342 per night (USD)
VRBO
\nCharming 3-bedroom townhome owned by artist in wonderful Lenox with WiFi, AC.\n
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This 3-bedroom townhome is perfect for your escape to Lenox. Nestled in the heart of the town, this charming property of ...
From $342 per night (USD)
VRBO
From $437 per night (USD)
VRBO
Comfortable Berkshires retreat on mtn resort, SISO
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Once a retreat for an NYC real estate family, this grand yet comfortable place in Jiminy Peak has retained the feel of a ...
From $437 per night (USD)
VRBO
From $181 per night (USD)
Expedia
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 $181 per night (USD)
Expedia
From $932 per night (USD)
VRBO
6-BR Expansive Berkshires Estate w Pool
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
(7/19/24): POOL RENOVATION UPDATE! We have just installed a BRAND NEW 15 x 30-foot pool, and she's ready for summer vi ...
From $932 per night (USD)
VRBO
From $847 per night (USD)
Expedia
LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Enjoy this very private, super comfortable, 1925 lake cottage, waterfront boathouse and dock for an entire Berkshire Sum ...
From $847 per night (USD)
Expedia
From $290 per night (USD)
VRBO
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 $290 per night (USD)
VRBO
From $501 per night (USD)
Expedia
Elegant Mountain View Retreat By Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Explore the best of the Berkshires at this private country retreat, minutes from the Williams campus, Jiminy Peak, world ...
From $501 per night (USD)
Expedia
$Idyllic Retreat; Hot Tub\/Sauna by Evergreen Home$
From $743 per night (USD)
VRBO
Idyllic Retreat; Hot Tub\/Sauna by Evergreen Home
Bedrooms:
3
Bathrooms:
4
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 $743 per night (USD)
VRBO
From $206 per night (USD)
Expedia
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 $206 per night (USD)
Expedia
Click For Pricing
VRBO
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
VRBO
Click For Pricing
Expedia
Berkshires Tranquil Retreat With Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Escape to your very own serene haven in Great Barrington with a private, in-ground pool on a 4-acre property. T ...
Click For Pricing
Expedia
From $553 per night (USD)
VRBO
Perfect for Thanksgiving Gatherings! Light-filled family home
Bedrooms:
4
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 $553 per night (USD)
VRBO
Click For Pricing
Expedia
Central Berkshire Craftsman - Long Terms Welcome!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This cute as a button cottage in a walkable residential neighborhood, is the perfect home base to explore the Berkshires ...
Click For Pricing
Expedia

Search Your Destination Now!

Berkshire Area Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 912 Rentals