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 $348 per night (USD)
VRBO
Club Wyndham Bentley Brook Resort - 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
*** Sanitation/Cleaning Update *** Wyndham resorts have always met the highest standards of cleanliness, and now we are ...
From $348 per night (USD)
VRBO
From $348 per night (USD)
Expedia
Club Wyndham Bentley Brook Resort - 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
*** Sanitation/Cleaning Update *** Wyndham resorts have always met the highest standards of cleanliness, and now we are ...
From $348 per night (USD)
Expedia
From $348 per night (USD)
VRBO
Club Wyndham Bentley Brook Resort - 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
*** Sanitation/Cleaning Update *** Wyndham resorts have always met the highest standards of cleanliness, and now we are ...
From $348 per night (USD)
VRBO
From $348 per night (USD)
Expedia
Club Wyndham Bentley Brook Resort - 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
*** Sanitation/Cleaning Update *** Wyndham resorts have always met the highest standards of cleanliness, and now we are ...
From $348 per night (USD)
Expedia
From $338 per night (USD)
VRBO
Tranquil 2-bedroom house with woodland and pasture views in Great Barrington
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Great Barrington countryside is waiting for you at this 2-bedroom house. Nestled in a serene setting surrounded by conse ...
From $338 per night (USD)
VRBO
From $348 per night (USD)
Expedia
Club Wyndham Bentley Brook Resort - 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
*** Sanitation/Cleaning Update *** Wyndham resorts have always met the highest standards of cleanliness, and now we are ...
From $348 per night (USD)
Expedia
From $470 per night (USD)
VRBO
Cabin Retreat in the Berkshire Woods
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Hayscent Hollow, where you'll find seclusion and serenity in the Berkshire woods. Featuring 3 bedroo ...
From $470 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Oak n' Spruce Resort in the Berkshires. Charming 2-bedroom in quaint Lee
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the Berkshires at Oak n' Spruce Resort in Lee. Amenities include indoor and outdoor pools, tennis courts, 18-hole ...
From $279 per night (USD)
Expedia
From $235 per night (USD)
VRBO
Immaculate Berkshires home! Close to museums, colleges, and outdoor activities.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Comfortably sleeping 6 with a large yard, screened in porch, and newly renovated bathroom, this charming 3-bedroom house ...
From $235 per night (USD)
VRBO
From $153 per night (USD)
Expedia
Cliffwood Cottage by Evergreen Home
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This charming retreat offers a beautifully designed two-bedroom apartment with a chef’s kitchen, central A/C, washer/dry ...
From $153 per night (USD)
Expedia
From $194 per night (USD)
VRBO
Cozy and conveniently located cottage nestled in the mountains
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to the Cottage at the Barrington House! The Barrington House is nestled in the serene Berkshires Mountains - wh ...
From $194 per night (USD)
VRBO
From $1161 per night (USD)
Expedia
Private estate with heated pool, guest house and incredible views
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
Welcome to the Barrington House! The Barrington House is nestled in the serene Berkshires Mountains - which have long b ...
From $1161 per night (USD)
Expedia
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VRBO
Bentley Brook 1-BR Mountainside resort sleeps 8- Available April 27-May 3
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
At the base of Jiminy Peak Ski Mountain, this resort is an exceptional choice for mountainside play, and skiing. The are ...
Click For Pricing
VRBO
$Spacious & Family-Ready Home w\/ Fenced Yard in Lee$
From $541 per night (USD)
Expedia
Spacious & Family-Ready Home w\/ Fenced Yard in Lee
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Indulge in the ultimate getaway and experience comfort, style, and convenience in our enchanting home. Step into an open ...
From $541 per night (USD)
Expedia
From $227 per night (USD)
VRBO
Bentley Brook the perfect home base for exploring nearby Berkshire County
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Ski-in and Ski-out your front door! Bentley Brook is situated right at the base of Jiminy Peak Ski Mountain, making this ...
From $227 per night (USD)
VRBO
From $112 per night (USD)
Expedia
Bentley Brook the perfect home base for exploring nearby Berkshire County
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Ski-in and Ski-out your front door! Bentley Brook is situated right at the base of Jiminy Peak Ski Mountain, making this ...
From $112 per night (USD)
Expedia
From $104 per night (USD)
VRBO
Bentley Brook the perfect home base for exploring nearby Berkshire County
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Ski-in and Ski-out your front door! Bentley Brook is situated right at the base of Jiminy Peak Ski Mountain, making this ...
From $104 per night (USD)
VRBO
From $155 per night (USD)
Expedia
Deluxe Queen Room with 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to this charming hotel in Lee. This awesome property features 1 soothing bedroom with a queen bed, perfect for a ...
From $155 per night (USD)
Expedia
From $216 per night (USD)
VRBO
Downtown Gateway to the Berkshires. Walk to Everything.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Experience the beauty of the Berkshires. Newly renovated two bedroom retreat in downtown, Lee. Steps from all the restau ...
From $216 per night (USD)
VRBO
From $931 per night (USD)
Expedia
Contemporary Berkshire Home with Views of Taconic Golf Course
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Discover peace and beauty at this one of a kind Berkshire home designed by Maya Lin (Vietnam Memorial Wall Architect). ...
From $931 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Bentley Brook 1-bedroom Mountainside ski resort in charming Hancock sleeps 8
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
At the base of Jiminy Peak Ski Mountain, this resort is an exceptional choice for mountainside play, and skiing. The are ...
From $220 per night (USD)
VRBO
From $508 per night (USD)
Expedia
New Custom Home Meets Nature’s Splendor in This Stunning Berkshires Retreat
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
A masterpiece of contemporary design, this new custom-built home is a harmonious blend of modern luxury and nature’s spl ...
From $508 per night (USD)
Expedia
From $335 per night (USD)
VRBO
Sunny 2-bed House in Downtown Lenox with WiFi and AC, Kitchenette
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This gem is perfectly situated on a quiet residential street in historic downtown Lenox. Take a short 3 minute walk to t ...
From $335 per night (USD)
VRBO
From $509 per night (USD)
Expedia
Spacious 4-bedroom house in peaceful Southfield with AC, WiFi and more!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Nestled in Southfield, this delightful house offers four bedrooms, including a king bed, two queen beds, a crib, and a f ...
From $509 per night (USD)
Expedia
From $505 per night (USD)
VRBO
Stockbridge Snug- cabin luxury just steps to lake!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Snug (an energy efficient home) was designed, renovated, and completed in June 2022. It serves as a cozy haven of re ...
From $505 per night (USD)
VRBO
From $420 per night (USD)
Expedia
Berkshire Mountain retreat with Urban eco-luxuries
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comfo ...
From $420 per night (USD)
Expedia
From $188 per night (USD)
VRBO
Entire cottage in Berkshire Villiage
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
With close access to the Ashuwillticook rail trail and a short drive to convenient shopping and restaurants, this is a p ...
From $188 per night (USD)
VRBO
From $538 per night (USD)
VRBO
Brand New Barn House
Bedrooms:
6
Bathrooms:
3
Sleeps:
6
The story of this house is so cool! But first ... This *brand new* barn house with woods, meadow, and stream sits on 3 a ...
From $538 per night (USD)
VRBO
From $330 per night (USD)
VRBO
The Hideaway: Berkshire Home - Village of Egremont
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our home in the village of Egremont (part of Great Barrington). Both the house and property are open and inv ...
From $330 per night (USD)
VRBO
From $540 per night (USD)
Expedia
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 $540 per night (USD)
Expedia
From $4327 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 $4327 per night (USD)
VRBO
From $236 per night (USD)
Expedia
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 $236 per night (USD)
Expedia
From $199 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 $199 per night (USD)
VRBO
From $1023 per night (USD)
Expedia
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)
Expedia
From $199 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 $199 per night (USD)
VRBO
From $199 per night (USD)
Expedia
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 $199 per night (USD)
Expedia
From $199 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 $199 per night (USD)
VRBO
From $199 per night (USD)
Expedia
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 $199 per night (USD)
Expedia
From $136 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 $136 per night (USD)
VRBO
From $136 per night (USD)
Expedia
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 $136 per night (USD)
Expedia
From $136 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 $136 per night (USD)
VRBO
From $136 per night (USD)
Expedia
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 $136 per night (USD)
Expedia
From $136 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 $136 per night (USD)
VRBO
From $1004 per night (USD)
Expedia
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 $1004 per night (USD)
Expedia
From $199 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 $199 per night (USD)
VRBO
From $486 per night (USD)
Expedia
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 $486 per night (USD)
Expedia
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
$Studio Suite, w\/ Full Kitchen at Bentley Brook, at Jiminy Peak Ski Mountain!!$
From $512 per night (USD)
Expedia
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)
Expedia
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 $397 per night (USD)
Expedia
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 $397 per night (USD)
Expedia
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)
Expedia
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)
Expedia
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 $354 per night (USD)
Expedia
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 $354 per night (USD)
Expedia
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)
Expedia
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)
Expedia
From $398 per night (USD)
VRBO
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)
VRBO
From $452 per night (USD)
Expedia
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)
Expedia
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
$Center of Lenox, cozy Apartment 2-bedroom<br>REVIEWS https:\/\/abnb.me\/kcBk7oCR6xb$
Click For Pricing
Expedia
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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Expedia
From $691 per night (USD)
VRBO
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)
VRBO
From $447 per night (USD)
Expedia
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 $447 per night (USD)
Expedia
Click For Pricing
VRBO
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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VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $377 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 $377 per night (USD)
VRBO
From $1307 per night (USD)
Expedia
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 $1307 per night (USD)
Expedia
$Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On\/Off Mountain$
From $250 per night (USD)
VRBO
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 $250 per night (USD)
VRBO
From $782 per night (USD)
Expedia
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 $782 per night (USD)
Expedia
From $250 per night (USD)
VRBO
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 $250 per night (USD)
VRBO
From $349 per night (USD)
Expedia
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 $349 per night (USD)
Expedia
From $1086 per night (USD)
VRBO
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 $1086 per night (USD)
VRBO
From $238 per night (USD)
Expedia
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)
Expedia
$Ski-In\/Ski-Out at Jiminy Peak in the Country Inn$
From $167 per night (USD)
VRBO
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 $167 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $365 per night (USD)
VRBO
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 $365 per night (USD)
VRBO
From $892 per night (USD)
Expedia
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)
Expedia
$Rustic-Chic Home w\/ Decks: Pool + Lake Access$
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VRBO
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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VRBO
From $347 per night (USD)
Expedia
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)
Expedia
From $308 per night (USD)
VRBO
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 $308 per night (USD)
VRBO
From $744 per night (USD)
Expedia
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 $744 per night (USD)
Expedia
From $289 per night (USD)
VRBO
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 $289 per night (USD)
VRBO
From $535 per night (USD)
Expedia
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 $535 per night (USD)
Expedia
From $514 per night (USD)
VRBO
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 $514 per night (USD)
VRBO
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Expedia
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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Expedia
$Charming Cottage w\/ Sauna, close to hiking trails, ski lodges & Great Barrington$
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 $344 per night (USD)
Expedia
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 $344 per night (USD)
Expedia
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 $653 per night (USD)
Expedia
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 $653 per night (USD)
Expedia
$Great Barrington\/Housatonic Getaway—bring your dog!$
From $218 per night (USD)
VRBO
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 $218 per night (USD)
VRBO
From $624 per night (USD)
Expedia
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 $624 per night (USD)
Expedia
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VRBO
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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VRBO
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Expedia
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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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 $735 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 $735 per night (USD)
Expedia
From $331 per night (USD)
VRBO
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 $331 per night (USD)
VRBO
From $725 per night (USD)
Expedia
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 $725 per night (USD)
Expedia
From $589 per night (USD)
VRBO
Fox Hollow Luxury Ranch Laurel Lake
Bedrooms:
5
Bathrooms:
4
Sleeps:
11
Awesome Berkshire Location. 1000 feet of Laurel Lake frontage shared with private dock , 2 canoes and 2 kayaks. Large o ...
From $589 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 $460 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 $460 per night (USD)
VRBO
$The Meadows House @ Otis Ridge w\/ 7-person hot tub$
From $308 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 $308 per night (USD)
Expedia

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