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 $576 per night (USD)
VRBO
The Maple House - Modern Retreat Near Town
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Summary: You will enjoy your stay at The Maple House, a beautifully restored mid-century modern retreat in the Berkshire ...
From $576 per night (USD)
VRBO
From $3804 per night (USD)
VRBO
Winthrop Estate - 1925 Charm & Modern Luxury
Bedrooms:
11
Bathrooms:
12
Sleeps:
24
Summary: I’m Jamie, the proud caretaker of the timeless and beautiful Winthrop Estate. This restored 1920s Gilded Age ma ...
From $3804 per night (USD)
VRBO
From $226 per night (USD)
VRBO
Deluxe One Bedroom and One Bathroom with Full Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Discover this lovely 1-bedroom gem in Hancock. Featuring a cozy bedroom with a king bed, a bathroom with luxurious ameni ...
From $226 per night (USD)
VRBO
From $196 per night (USD)
VRBO
Deluxe Two Bedroom and Two Bathroom with Full Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover the beauty of Hancock! Beautiful and scenic neighborhood. Enjoy the breath taking views in the 1 king bedroom a ...
From $196 per night (USD)
VRBO
From $118 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 $118 per night (USD)
VRBO
From $118 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 $118 per night (USD)
VRBO
From $118 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 $118 per night (USD)
VRBO
From $147 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
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 $147 per night (USD)
VRBO
From $147 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $147 per night (USD)
VRBO
From $147 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $147 per night (USD)
VRBO
From $147 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $147 per night (USD)
VRBO
From $118 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 $118 per night (USD)
VRBO
From $118 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 $118 per night (USD)
VRBO
From $1023 per night (USD)
VRBO
Discover AppleCreek. BEST OF EVERYTHING, NEAR EVERYTHING
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Perfectly situated in Lenox MA, this beautiful open 5 acre property offers an oasis of relaxation with views of October ...
From $1023 per night (USD)
VRBO
From $994 per night (USD)
VRBO
Private luxury with heated pool less than 10 min from downtown Great Barrington
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Perfect location for summer, fall foliage, and winter skiing! A recently renovated home on 10 acres less than 10 minutes ...
From $994 per night (USD)
VRBO
From $363 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 $363 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 $190 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 $190 per night (USD)
VRBO
From $519 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 $519 per night (USD)
VRBO
From $724 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 $724 per night (USD)
VRBO
$Studio Suite, w\/ Full Kitchen at Bentley Brook, at Jiminy Peak Ski Mountain!!$
From $503 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 $503 per night (USD)
VRBO
From $141 per night (USD)
VRBO
Spacious 2-bedroom apartment located in downtown Williamstown.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This luxuriously appointed, fully furnished 2-bedroom, 2-bathroom apartment is located in downtown Williamstown. The apa ...
From $141 per night (USD)
VRBO
From $245 per night (USD)
VRBO
Berkshire Mountain Cottage: in the Heart of the Berkshires
Bedrooms:
1
Bathrooms:
3
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 $267 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 $267 per night (USD)
VRBO
From $367 per night (USD)
VRBO
Berkshire Mountainside Condo
Bedrooms:
3
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 $367 per night (USD)
VRBO
From $403 per night (USD)
VRBO
Clean & Modern space with a mix of original warmth and charming renovation.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to "The Hideaway On Main " in Stockbridge Center. Now booking for 20-29 day stays this summer. Our recently r ...
From $403 per night (USD)
VRBO
From $572 per night (USD)
VRBO
18 Century farmhouse with modern conveniences set on 47 magnificent acres
Bedrooms:
4
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
From $398 per night (USD)
Expedia
Historic Stone Church in The Berkshires
Bedrooms:
2
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 $398 per night (USD)
Expedia
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 $341 per night (USD)
VRBO
Historic Lenox Village Summer Rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Historic Lenox Village Condo available for summer 2024. Beautifully Furnished. Walking distance to shopping, dining, gro ...
From $341 per night (USD)
VRBO
$Center of Lenox, cozy Apartment 2-bedroom<br>REVIEWS https:\/\/abnb.me\/kcBk7oCR6xb$
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VRBO
Center of Lenox, cozy Apartment 2-bedroom<br>REVIEWS https:\/\/abnb.me\/kcBk7oCR6xb
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
READ OUR AIRBNB REVIEWS https://abnb.me/kcBk7oCR6xb Our two story apartment is spacious and cozy all in one. Built i ...
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VRBO
From $691 per night (USD)
Expedia
Romantic and Secluded Berkshire's Gem
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Beautiful log cabin in the middle of private 5 acres of woods with all of the 21st-century amenities. We are 5 minutes a ...
From $691 per night (USD)
Expedia
From $413 per night (USD)
VRBO
Relax between your Berkshire adventures! Easy walk to town! Centrally located!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Owner operated with pride! Our vacation home in Lee Massachusetts is centrally located to ALL THINGS BERKSHIRES! In the ...
From $413 per night (USD)
VRBO
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Expedia
Bentley Brook at Jiminy Peak ^ Studio
Bedrooms:
1
Bathrooms:
0
Sleeps:
4
Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski ...
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Expedia
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VRBO
Historic 1817 Berkshire Farmhouse- Close to Everything!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
View our Superhost reviews here: https://www.airbnb.com/rooms/26598493? preview_for_ml=true&source_impression_id=p3_1675 ...
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VRBO
From $374 per night (USD)
VRBO
Elegant Lake Buel Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Totally renovated and updated lake house with access to Lake Buel right across the quaint road. Sit on your large screen ...
From $374 per night (USD)
VRBO
From $543 per night (USD)
VRBO
New England Family Home with Hot Tub and Pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Family-Friendly New England style 5 bedroom home located in the Berkshire hills, remote setting minutes from Stockbridge ...
From $543 per night (USD)
VRBO
$Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On\/Off Mountain$
From $232 per night (USD)
Expedia
Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On\/Off Mountain
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to the Jurassic Era! This is the most epic suite in all of the Berkshires! Brand new, you will love a ...
From $232 per night (USD)
Expedia
From $790 per night (USD)
VRBO
Beautiful 4 Bedroom Townhouse in the Berkshires at Jiminy Peak Resort
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Located slope side at Jiminy Peak mountain resort in Hancock, MA, this townhouse offers guests 4 bedrooms, 3 bathrooms, ...
From $790 per night (USD)
VRBO
From $232 per night (USD)
Expedia
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: You want to pop out of bed, walk out your door, and be right on the mountain - this is the place for you. This ...
From $232 per night (USD)
Expedia
From $352 per night (USD)
VRBO
Berkshires Cabin 2 Mi to Appalachian Trail!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
An authentic Berkshire Mountains experience awaits in Otis at this 3-bedroom, 2-bathroom vacation rental by Lindal Cedar ...
From $352 per night (USD)
VRBO
From $992 per night (USD)
Expedia
Quintessential 6-BR Berkshires Lodge
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Summary: Retreat to the beauty of the Berkshires in this stunning, newly renovated lodge with a brand new pool! Features ...
From $992 per night (USD)
Expedia
From $238 per night (USD)
VRBO
Private apartment in beautiful country barn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Berkshire living at its best! This lovely shaker barn on 2 open acres has three apartments. All are private. Rent one o ...
From $238 per night (USD)
VRBO
$Ski-In\/Ski-Out at Jiminy Peak in the Country Inn$
From $158 per night (USD)
Expedia
Ski-In\/Ski-Out at Jiminy Peak in the Country Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled in the heart of the Berkshires, Jiminy Peak is the ultimate year-round escape. Whether you’re here for skiing, s ...
From $158 per night (USD)
Expedia
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VRBO
Bentley Brook at Jiminy Peak ^^ 2 Bedroom
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 ...
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VRBO
From $343 per night (USD)
Expedia
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to Lake Ashmere! Our newly and completely renovated cottage features two bedrooms with comfy queen size beds, a ...
From $343 per night (USD)
Expedia
From $892 per night (USD)
VRBO
Lenox Grand Colonial with Pool by Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This 4 bedroom spacious home sits on a quiet cul-de-sac beneath October Mountain, with a picturesque back yard complete ...
From $892 per night (USD)
VRBO
$Rustic-Chic Home w\/ Decks: Pool + Lake Access$
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Expedia
Rustic-Chic Home w\/ Decks: Pool + Lake Access
Bedrooms:
3
Bathrooms:
6
Sleeps:
6
Natural beauty and upscale amenities pair perfectly together at this vacation rental! Nestled in the Otis Wood Lands com ...
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Expedia
From $347 per night (USD)
VRBO
Main Street Delight 1bedroom
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located on Main Street in downtown Lenox. A beautifully space fully equipped for all your needs. The eat-in kitchen has ...
From $347 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Beachwood Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unique small cottage in the sought-after Beachwood community situated 2 miles from Tanglewood on Stockbridge Bowl. Featu ...
From $306 per night (USD)
Expedia
From $593 per night (USD)
VRBO
Stylish Mid-century Modern Berkshires Cape
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Stylish, fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires! Enjoy the large, sunny yard an ...
From $593 per night (USD)
VRBO
From $302 per night (USD)
Expedia
Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Our property is a renovated 1770s stage coach stop, with original wood floors. The upstairs of our home (with separate e ...
From $302 per night (USD)
Expedia
From $486 per night (USD)
VRBO
Little Longbow Lakefront Chalet
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to your Berkshire Oasis! This rustic lakefront chalet is ideally located right in the heart of the Berkshires in ...
From $486 per night (USD)
VRBO
From $501 per night (USD)
Expedia
Elegant Pittsfield Home Near Downtown & Skiing!
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Experience a fun-filled group getaway at this Pittsfield vacation rental! Named 'The Duchess of Pomeroy' for its charmin ...
From $501 per night (USD)
Expedia
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VRBO
Loft Style Cabin In West Stockbridge, Book Now!
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Summary: Custom built loft style home in beautiful West Stockbridge. You’ll love how the outdoors streams into the house ...
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VRBO
$Charming Cottage w\/ Sauna, close to hiking trails, ski lodges & Great Barrington$
From $326 per night (USD)
VRBO
Charming Cottage w\/ Sauna, close to hiking trails, ski lodges & Great Barrington
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Perfect Refuge in a Charming Berkshire Cottage with Vaulted Ceilings, Two-Person Sauna, Wrap Around Deck, Amazing Sunlig ...
From $326 per night (USD)
VRBO
From $313 per night (USD)
VRBO
Skiing & Hiking: Water-View Home in the Berkshires
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
2,262 Sq Ft | Ping-Pong Table | Nestled on Mill Pond | < 7 Mi to Dwtn Great Barrington Take a break from the city and b ...
From $313 per night (USD)
VRBO
From $309 per night (USD)
VRBO
Cozy Cabin on Lake Mahkeenac
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy cabin located in the popular Beachwood community which is 2 miles from Tanglewood on Stockbridge Bowl, close to Kr ...
From $309 per night (USD)
VRBO
From $729 per night (USD)
VRBO
Renovated, Five Bedrooms In Historic Williamstown
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
Summary: Spacious and renovated, this large family home in Williamstown offers over 3400 square feet of living space. Wi ...
From $729 per night (USD)
VRBO
$Great Barrington\/Housatonic Getaway—bring your dog!$
From $214 per night (USD)
Expedia
Great Barrington\/Housatonic Getaway—bring your dog!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome! Great location in the Housatonic village of Great Barrington with big yard, walkable streets and an excellent f ...
From $214 per night (USD)
Expedia
From $574 per night (USD)
VRBO
Perfect location in the heart of downtown Lenox
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
If you want to feel like you're truly away, but still have access to a great lifestyle, this is the rental for you! St ...
From $574 per night (USD)
VRBO
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Expedia
Charming cottage in Norman Rockwell's Stockbridge with two decks!
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Light, sunny, charming 3-4 bedroom cottage built in 1832 in Norman Rockwell's Stockbridge, a five minute walk to the Red ...
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Expedia
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VRBO
sweet dreams retreat
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Located near York Lake National Park and many other lakes. Equipped with everything you need for leisure or work. Includ ...
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VRBO
From $324 per night (USD)
Expedia
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: You want to pop out of bed, walk downstairs and be right on the mountain - this is the place to be. This Styli ...
From $324 per night (USD)
Expedia
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VRBO
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
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 ...
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VRBO
From $548 per night (USD)
Expedia
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This hotel/resort is at the base of the ski lift for Jiminy Mountain. And, when you are not on the slopes, it features a ...
From $548 per night (USD)
Expedia
From $534 per night (USD)
VRBO
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Prior guests of this charming house next to the forest trails have already reserved their return stay for next year to e ...
From $534 per night (USD)
VRBO
From $615 per night (USD)
VRBO
Great Barrington 4BR home on 3 wooded acres walking distance to town!
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Bring the whole family to our Great Barrington home on 'The Hill'. With 4 bedrooms, 4 bathrooms, outdoor deck, screened ...
From $615 per night (USD)
VRBO
From $655 per night (USD)
VRBO
Wildlife Retreat in the Forest
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Home in the Birkshires! 12 minutes away from Jacob's Pillow, 2.5 hours away from NYC. Our Beautiful Lindal Cedar Contem ...
From $655 per night (USD)
VRBO
$The Meadows House @ Otis Ridge w\/ 7-person hot tub$
From $305 per night (USD)
Expedia
The Meadows House @ Otis Ridge w\/ 7-person hot tub
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Relax in a beautiful mountain setting at this 4-season ski house within walking distance of the slopes at Otis Ridge Ski ...
From $305 per night (USD)
Expedia
From $687 per night (USD)
VRBO
Private Island - Largest Fresh Water Reservoir in Mass....
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Rustic.. Not fancy... It's a cabin... 2 bedroom, one with Queen the other with twin bunkbeds... 2 couches could sleep ex ...
From $687 per night (USD)
VRBO
From $186 per night (USD)
Expedia
Garfield Townhouse in the Berkshires on Main St
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Cozy Townhouse on Main St in Lee , the entrance to the Berkshires. The townhouse is two stories with 2 Bedrooms, 1 1/2 ...
From $186 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Rustic Getaway with Extraordinary Vista
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
With exceptional lighting, Sky House overlooks a gorgeous , sloping yard in peaceful Monterey. Close to Lake Garfield an ...
From $469 per night (USD)
VRBO
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Expedia
Cozy two-bedroom ranch 15 minutes from Butternut Ski Resort - 90-day minimum
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy our comfortable, cozy, fully furnished two-bedroom, two-bathroom ranch (1,500 square-feet) in the Berkshires (Mont ...
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Expedia
$Berkshire Ski House \/ Pittsfield$
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VRBO
Berkshire Ski House \/ Pittsfield
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Close to several popular family friendly Berkshire ski areas. Theaters restaurants and shopping are all walking distan ...
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VRBO
From $507 per night (USD)
Expedia
Great Barrington Get Away
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Charming home steps away from downtown Great Barrington. Lots of modern amenities, close to all the fantastic cultural ...
From $507 per night (USD)
Expedia
From $581 per night (USD)
VRBO
Art House! Spacious Getaway By Mass Moca
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
This newly renovated Victorian curated by the local Grant Larkin Design Team is a great space for large groups, with eas ...
From $581 per night (USD)
VRBO
From $227 per night (USD)
Expedia
mountain refuge
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Extended stays are welcome! Stay in our little Mobile Home, clean, sweet and unique. The house is adjacent to Breakshir ...
From $227 per night (USD)
Expedia
From $306 per night (USD)
VRBO
3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Spacious living/kitchen area, located on a quiet street and central location walkable to campus and restaurants, museums ...
From $306 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Stockbridge Home: Walk to Town Beach!
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Escape to a lake retreat with this 3-bedroom, 1-bathroom vacation rental home in Stockbridge. Stockbridge Bowl's grassy ...
From $276 per night (USD)
Expedia
From $1097 per night (USD)
VRBO
ONTARA....
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ONTARA, Place of the New Light...in the Berkshires...on the mountainside, with the back of the property on the New York ...
From $1097 per night (USD)
VRBO
From $318 per night (USD)
Expedia
Home in Great Barrington
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Central and Private!! Just steps away from historic downtown Great Barrington and East Mountain Hiking trails. Enjoy su ...
From $318 per night (USD)
Expedia
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VRBO
Restored Historic Home Half Mile to Ski Resort!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to The Berkshires and explore endless adventures in the area’s mountains, forests, and arts venues! This 4-bedroo ...
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VRBO
From $1262 per night (USD)
VRBO
Charming 6 Bdrm Countryside Stay, Sauna & HotTub
Bedrooms:
6
Bathrooms:
6
Sleeps:
18
This stunning 6 bedroom, 5.5 bath home is the perfect blend of charm, privacy, and modern comfort. Thoughtfully designed ...
From $1262 per night (USD)
VRBO
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VRBO
River Orchard Meadow
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
Tasteful, comfortable & tidy family Berkshire home located on the Housatonic River minutes from all the Berkshire offeri ...
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VRBO
From $721 per night (USD)
Expedia
Berkshires Lakefront Retreat by Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to your serene retreat nestled on 4 private acres. This newly renovated 4BR/2.5BA home offers breathtaking views ...
From $721 per night (USD)
Expedia
$1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On\/Off, Fully Redone Count$
From $232 per night (USD)
VRBO
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On\/Off, Fully Redone Count
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to the Woodlands. This unique Suite lies right on Jiminy Peak Mountain within the Country Inn. 1st Fl ...
From $232 per night (USD)
VRBO
From $269 per night (USD)
VRBO
Cozy Home on 17 acres in W Stockbridge. Close to the Pike, Slopes, Tanglewood
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Enjoy your stay in heart of the Berkshires! This 3 bedroom, 2 bath ranch vacation house in set on 17 private acres. En ...
From $269 per night (USD)
VRBO
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VRBO
Family fun @ The Ponds at Foxhollow Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Ponds at Foxhollow is a distinctive residential community in Lenox, MA. The community features elegantly designed ho ...
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VRBO
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Expedia
BERKSHIRES CHARM! Lenox, Tanglewood! SUMMER ONLY, or LongTerm Rental. Location!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
LOCATION! **Enjoy the culture and beauty of a Berkshires/Tanglewood summer from cozy furnished apartments of this 1840 ...
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Expedia
From $611 per night (USD)
VRBO
Linden by AvantStay | Countryside Berkshire Escape
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Welcome to Linden! Surrounded by tons of space and trees, this 4BR retreat gives your group the style, room, and privacy ...
From $611 per night (USD)
VRBO
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Expedia
Eastbungalow
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
About this space Welcome to the Berkshires!!! A very large duplex apartment with own entrance and a porch to relax in. T ...
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Expedia
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VRBO
Charming Ashley Falls Getaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
About this space The home is set back from the road in a quiet rural neighborhood, nestled among stately pines. There is ...
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VRBO
From $590 per night (USD)
VRBO
Moores · Berkshire Mountain Top Chalet
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
Summary: Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fi ...
From $590 per night (USD)
VRBO
From $469 per night (USD)
VRBO
Treetop Hideaway in Tyringham
Bedrooms:
1
Bathrooms:
5
Sleeps:
8
Summary: For your upcoming stay, look no further than this airy, secluded log cabin overlooking the beautiful Tyringham ...
From $469 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
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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 ...
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VRBO
From $1130 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 $1130 per night (USD)
VRBO
From $305 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 $305 per night (USD)
VRBO
From $465 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 $465 per night (USD)
Expedia

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