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

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VRBO
Cozy Condo, walk to town, private and bright
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy this lovely sanctuary! A lovely place to get away from it all, while still being a ten minute stroll from the cent ...
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VRBO
From $444 per night (USD)
VRBO
Treetop Hideaway in Tyringham
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Summary: For your upcoming stay, look no further than this airy, secluded log cabin overlooking the beautiful Tyringham ...
From $444 per night (USD)
VRBO
From $572 per night (USD)
VRBO
18 Century farmhouse with modern conveniences set on 47 magnificent acres
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Berkshire Farm House rental combining the charm of an original 18 Berkshire with modern conveniences and luxury ameniti ...
From $572 per night (USD)
VRBO
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Expedia
Condo with Resort Amenities in Lenox
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy a relaxing getaway in this resort-style condo with a view of the pond. This is a secluded resort nestled in the he ...
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Expedia
From $4255 per night (USD)
VRBO
Sunset Falls: A Berkshire Mountain Luxury Retreat
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
Welcome to Sunset Falls, where luxury meets nature in this modern architecturally significant home on 167 private acres. ...
From $4255 per night (USD)
VRBO
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Expedia
Home in the woods with Views, Quiet, Gardens, near Tanglewood,
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Be secluded but within a short drive of the many cultural and natural attractions of this beautiful area. This lovely 3 ...
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Expedia
From $258 per night (USD)
VRBO
Cozy Cabin in the Berkshires
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Our cozy cabin rental is the perfect escape for those seeking tranquility and natural beauty. Truly a four season cabin, ...
From $258 per night (USD)
VRBO
From $452 per night (USD)
VRBO
1840 Village Farmhouse with Modern Comforts
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Three bedrooms (2 queen; 1 single) plus den/guest room with queen-size pull-out couch. Comfortable living/dining area w ...
From $452 per night (USD)
VRBO
From $517 per night (USD)
VRBO
Gem of the Berkshires. Mountain View. Short walk to lake & downtown.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
A lovely property with gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tan ...
From $517 per night (USD)
VRBO
From $569 per night (USD)
VRBO
Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
For 2023, a massive gut reno has been completed, adding a 24ft wide sunroom overlooking the lake, 2 new bedrooms and a b ...
From $569 per night (USD)
VRBO
From $375 per night (USD)
VRBO
Spacious Historic Home in the Berkshires!
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Just minutes from downtown Pittsfield and surrounded by the beauty of the Berkshires is this lovely 5-bedroom, 2-bathroo ...
From $375 per night (USD)
VRBO
From $741 per night (USD)
Expedia
Escape to The Berkshires w/Pool by Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This 4Br home is filled with cheeky pop art, stylish comfortable spaces and all the amenities you need for the ideal Ber ...
From $741 per night (USD)
Expedia
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VRBO
Perfect for Entertaining and Relaxation in the Berkshires!Furnished Country Home
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Escape to Lake Buel for a serene getaway in the Berkshires. This spacious rental home sleeps up to 12 people and feature ...
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VRBO
From $358 per night (USD)
Expedia
Historic Stone Church in The Berkshires
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Hinterland Hall was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Plac ...
From $358 per night (USD)
Expedia
From $635 per night (USD)
VRBO
Cape Home In the Beautiful Berkshires - Near Lenox & Bousquet
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Cozy Cape Cod home in the beautiful Berkshires in desired neighborhood. Close to Bousquet Ski Resort, Wild Acres, Tangle ...
From $635 per night (USD)
VRBO
From $364 per night (USD)
VRBO
Berkshire Mountainside Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Fabulous 4 season Berkshire condo rental has room for 9 guests. Ski from this condo to Bousquet Ski Area; enjoy spring r ...
From $364 per night (USD)
VRBO
From $545 per night (USD)
VRBO
Berkshires Colonial on 2 Acres by Evergreen Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
A Berkshires grand colonial home, on 2.7 private acres is the perfect home-base for your getaway to the Berkshires. Loc ...
From $545 per night (USD)
VRBO
From $631 per night (USD)
Expedia
The Penthouse, Downtown Lenox by Evergreen Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summer in Lenox! Now available August 1 - Labor Day!` Luxury Awaits... This downtown Lenox 3 BR, 2 BA apartment just u ...
From $631 per night (USD)
Expedia
From $277 per night (USD)
VRBO
Endearing cottage in the Berkshires, walking distance to downtown and Mass MoCA.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
0.7 miles to MASS MoCA & downtown. Close drive to Williamstown MA & VT. Hiking, museums, and skiing are close by. On-pr ...
From $277 per night (USD)
VRBO
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Expedia
Cabin in the woods w cedar Hot Tub + private pond
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
About this space The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests ...
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Expedia
From $387 per night (USD)
VRBO
Great Barrington Farmhouse near Lake Mansfield
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
72 CHill Road is a cozy 1860’s farm house with mid-century modern flair. A 7-minute drive to downtown or Butternut, this ...
From $387 per night (USD)
VRBO
From $191 per night (USD)
VRBO
Bentley Brook Resort 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
At the base of Jiminy Peak Ski Mountain, Bentley Brook resort is an exceptional choice for mountainside play. The area d ...
From $191 per night (USD)
VRBO
From $319 per night (USD)
VRBO
Walk to campus; open concept kitchen/living;nature trail at end of this quiet st
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
A private townhouse w/ 3 bedrooms (1 with Queen on main floor, 2 on second floor -King bed and twin bed the two upstairs ...
From $319 per night (USD)
VRBO
From $245 per night (USD)
VRBO
Berkshire Mountain Cottage: in the Heart of the Berkshires
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Berkshire Mountain Cottage is a warm and cozy hideaway located in the Berkshire hills. Its located between North Egremon ...
From $245 per night (USD)
VRBO
From $381 per night (USD)
VRBO
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Recently renovated home in the exclusive Lake Buel community very close to the Appalachian Trail, Butternut Ski Area, Do ...
From $381 per night (USD)
VRBO
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Expedia
1847 New Marlborough Farmhouse. a 4-BR home right in our quiet village.
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Our home is located in the beautiful village of New Marlborough - 15/20 min. from Gt. Barrington & Sheffield. The porch ...
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Expedia
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VRBO
Family friendly house with two complete units, private deck and yard.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This newly remodeled house features two complete units (upstairs and downstairs) with separate entrances and a connectin ...
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VRBO
From $219 per night (USD)
Expedia
Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
New listing ! Looking for a centrally located place to stay? This Berkshires home is 5 minutes from Bousquet Ski Resort ...
From $219 per night (USD)
Expedia
From $736 per night (USD)
VRBO
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
Bedrooms:
3
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 $736 per night (USD)
VRBO
From $222 per night (USD)
Expedia
Park Street Penthouse Apartment
Bedrooms:
1
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 $222 per night (USD)
Expedia
From $396 per night (USD)
VRBO
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)
VRBO
From $486 per night (USD)
Expedia
Outdoor Sauna, Hot tub, Fire Pit, Dogs Welcome!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax with the whole family or escape with your partner for a romantic getaway to Lovers Lane. Surrounded by trees and s ...
From $486 per night (USD)
Expedia
From $564 per night (USD)
VRBO
Spring time fun time. Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
***Spring Time is here. Stroll the town or enjoy a scenic walk then warm right up in our OUTDOOR Hot Tub after a long da ...
From $564 per night (USD)
VRBO
From $414 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 $414 per night (USD)
VRBO
From $529 per night (USD)
VRBO
1 Bedroom Deluxe Condo, Sleeps 8, at Bentley Brook, Jiminy Peak Ski Mountain!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
8
This spacious one-bedroom resort suite measures approximately 780 to 880 square feet. You will enjoy two queen beds in t ...
From $529 per night (USD)
VRBO
From $738 per night (USD)
VRBO
2 Bedroom Deluxe Condo 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 $738 per night (USD)
VRBO
From $512 per night (USD)
VRBO
Studio Suite, w/ Full Kitchen at Bentley Brook, at Jiminy Peak Ski Mountain!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This spacious studio suite measures approximately 400 square feet. You will enjoy one queen Murphy bed and one queen sle ...
From $512 per night (USD)
VRBO
From $337 per night (USD)
Expedia
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Bedrooms:
1
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 $337 per night (USD)
Expedia
From $303 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 $303 per night (USD)
VRBO
From $326 per night (USD)
VRBO
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Dublinshire Farm is a giant shaker barn that has three private apartments. This newest listing, #3, is a charming 2 sto ...
From $326 per night (USD)
VRBO
From $1163 per night (USD)
VRBO
Stockbridge Retreat w/ Pool & Hot Tub!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Escape to the Berkshires and indulge in the ultimate experience at this luxurious 4-bedroom, 3.5-bathroom house. Situate ...
From $1163 per night (USD)
VRBO
From $486 per night (USD)
Expedia
Berkshire Retreat- Stone's throw to downtown Lenox
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Berkshire Retreat - A stone's throw to downtown Lenox Our calendar is updated in real-time & our nightly rates are accu ...
From $486 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
From $454 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 $454 per night (USD)
Expedia
From $276 per night (USD)
VRBO
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 $276 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $484 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 $484 per night (USD)
VRBO
From $191 per night (USD)
Expedia
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Bedroom with large master bath. Lockoff room with private front entrance. Kayak, swim, or bring your paddleboard or boa ...
From $191 per night (USD)
Expedia
From $584 per night (USD)
VRBO
Modern Cabin Near Tanglewood
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to West Stockbridge in the Berkshires! This newly renovated modern cabin is nestled amongst the trees and locate ...
From $584 per night (USD)
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
From $421 per night (USD)
VRBO
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)
VRBO
From $343 per night (USD)
VRBO
Fox Hollow Lakeside Condo, Minutes to Tanglewood
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Five bedroom condo on 223 acre manicured estate in the heart of the Berkshires. Laurel Lake views from most rooms and us ...
From $343 per night (USD)
VRBO
From $742 per night (USD)
VRBO
2 Bedroom Deluxe Condo w/ Full Kitchen at Bentley Brook, Jiminy Peak Ski Mount!!
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 $742 per night (USD)
VRBO
From $855 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 $855 per night (USD)
VRBO
From $274 per night (USD)
VRBO
Quiet Cabin On Over 12 Acres Of Woods!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Summary: This home features both modern finishes & New England charm. Large open great room, chef's kitchen & brick fire ...
From $274 per night (USD)
VRBO
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Expedia
Enchanting Cottage, Come Enjoy Nature!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Experience the captivating charm of a 1920 cottage. Come enjoy and indulge in the tranquility of the spacious f ...
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Expedia
From $758 per night (USD)
VRBO
2 Bedroom Condo, at Jiminy Peak Ski Mountain, Bentley Brook Resort!!
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 $758 per night (USD)
VRBO
From $907 per night (USD)
Expedia
2 Bedroom Deluxe Condo at Jiminy Peak Mountain, Skiing, Bentley Brook Resort!
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 $907 per night (USD)
Expedia
From $855 per night (USD)
VRBO
2 Bedroom Deluxe Condo w/ Kitchen, at Jiminy Peak Ski Mountain, 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 $855 per night (USD)
VRBO
From $878 per night (USD)
VRBO
2 Bedroom Deluxe Condo at Jiminy Peak Ski Mountain, Bentley Brook Resort!
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 $878 per night (USD)
VRBO
$A Cozy 100 yr old New England Berkshires Dutch Colonial.\n\nLong term available.$
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VRBO
A Cozy 100 yr old New England Berkshires Dutch Colonial.\n\nLong term available.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Cozy New England Dutch Colonial on a large corner 1/2 acre lot, closed in with fence and gate to close in driveway, sur ...
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VRBO
From $572 per night (USD)
Expedia
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski ...
From $572 per night (USD)
Expedia
From $1151 per night (USD)
VRBO
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Bedrooms:
3
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 $1151 per night (USD)
VRBO
From $430 per night (USD)
VRBO
Family Friendly Raised Cape in the Center of Lenox Village
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This renovated raised cape is in the center of historic Lenox, MA. 3 large bedrooms. 2 full bathrooms. Master bedroom ha ...
From $430 per night (USD)
VRBO
From $233 per night (USD)
VRBO
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to modern country comfort. This unique Suite lies right on Jiminy Peak Mountain within the Country Inn ...
From $233 per night (USD)
VRBO
From $269 per night (USD)
VRBO
Off-Season Sabbatical Retreat Rates!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
New off-season rental option!! Please inquire for special monthly rates from November 2025 through April 2026! Perfect ...
From $269 per night (USD)
VRBO
From $885 per night (USD)
VRBO
2 Bedroom Condo, Sleeps 8, Kitchen, Jiminy Peak Ski Mountain, 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 $885 per night (USD)
VRBO
From $282 per night (USD)
VRBO
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Great for outdoor enthusiasts, this 3-bedroom, 2.5-bathroom vacation rental home features a balcony, a deck, a patio, an ...
From $282 per night (USD)
VRBO
From $207 per night (USD)
VRBO
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: You want to pop out of bed, walk down hall, and be right on the mountain This 1BR 1 BA Ground Floor Unit Charm ...
From $207 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $271 per night (USD)
VRBO
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: You want to pop out of bed, walk down hall, and be right on the mountain This 1BR 1 BA off lobby Unit has som ...
From $271 per night (USD)
VRBO
Click For Pricing
Expedia
1 Bedroom Deluxe Condo, Sleeps 6, Skiing at Jiminy Peak Mountain, Bentley Brook!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This spacious one-bedroom resort suite measures approximately 780 to 880 square feet. You will enjoy two queen beds in t ...
Click For Pricing
Expedia
From $889 per night (USD)
VRBO
2 Bedroom Condo, Sleeps 8, Skiing, Jiminy Peak Mountain, Bentley Brook Resort!!
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)
VRBO
From $217 per night (USD)
Expedia
A-Frame Cabin w/ Furnished Deck in Becket!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Built in 1974 | Private Acreage & Scenic Surroundings | Fireside Relaxation | EV Charger Embrace a slower pace of life ...
From $217 per night (USD)
Expedia
From $1224 per night (USD)
VRBO
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
Bedrooms:
4
Bathrooms:
7
Sleeps:
12
Wellspring is a sprawling Berkshire escape with unparalleled views of the surrounding mountains. This gorgeous home has ...
From $1224 per night (USD)
VRBO
From $454 per night (USD)
Expedia
Near Tanglewood: Historic Summer Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Newly-renovated Berkshire Hills home where rustic charm meets modern elegance. Ideal for families or groups. The open-st ...
From $454 per night (USD)
Expedia
From $199 per night (USD)
VRBO
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 $199 per night (USD)
VRBO
From $801 per night (USD)
Expedia
Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Discover a unique getaway in the heart of Stockbridge, Massachusetts, at the historic rectory of St. Joseph's Church. Pe ...
From $801 per night (USD)
Expedia
From $889 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 $889 per night (USD)
VRBO
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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 & ...
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Expedia
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VRBO
10 Minutes to Ski Butternut! Dogs Welcome!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Close to Butternut and Catamount Ski Areas! This is a 3 month winter rental for $3,300 per month including utilities. Fa ...
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VRBO
From $200 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 $200 per night (USD)
VRBO
From $168 per night (USD)
VRBO
Mountainside Condo Ski In Ski Out
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Recently Renovated!! Nestled in the Berkshires, a getaway to Jiminy Peak offers everything you need, so close to home. J ...
From $168 per night (USD)
VRBO
From $373 per night (USD)
Expedia
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 $373 per night (USD)
Expedia
From $681 per night (USD)
VRBO
Guesthouse Cabin vacation rentals in Berkshire County
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Undermountain Lodge offers an escape to a serene cabin, nestled between pristine natural spring lakes with panoramic mou ...
From $681 per night (USD)
VRBO
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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 ...
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Expedia
From $483 per night (USD)
VRBO
Historic New Lebanon Hideaway on 33 Private Acres!
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Get the cozy bed and breakfast feel all to yourself at this New Lebanon vacation rental. This sprawling home with 5 beds ...
From $483 per night (USD)
VRBO
From $560 per night (USD)
VRBO
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Family or couples getaway! 3 bedrooms plus library, Sleeps 6-8 A beautiful 3050 Sq. Ft., 2-Story Colonial and attached ...
From $560 per night (USD)
VRBO
From $635 per night (USD)
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 ...
From $635 per night (USD)
VRBO
From $3774 per night (USD)
VRBO
Magical Country Retreat in the Berkshires, 10min from ski slopes.
Bedrooms:
9
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 $3774 per night (USD)
VRBO
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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 ...
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VRBO
From $207 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 $207 per night (USD)
VRBO
From $347 per night (USD)
VRBO
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 $347 per night (USD)
VRBO
From $762 per night (USD)
Expedia
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 $762 per night (USD)
Expedia
$Berkshires Retreat with Fall Foliage, Views & Cozy Fireplace Near Town. \n\n$
From $566 per night (USD)
VRBO
Berkshires Retreat with Fall Foliage, Views & Cozy Fireplace Near Town. \n\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This contemporary, light-filled 3BR, 2.5BA home is less than a mile from Lake Mansfield and downtown Great Barrington, w ...
From $566 per night (USD)
VRBO
From $126 per night (USD)
Expedia
Private Guest Suite in 1771 Farmhouse - 5 minutes to Jiminy Peak
Bedrooms:
1
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)
Expedia
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VRBO
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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VRBO
From $567 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 $567 per night (USD)
Expedia
From $521 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 $521 per night (USD)
VRBO
From $916 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 $916 per night (USD)
Expedia

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