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 $558 per night (USD)
VRBO
Charming Long Pond Vacation Home in the Berkshires
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Lond Pond Road is considered one of the most beautiful and peaceful roads in th Berkshires. It is the perfect location t ...
From $558 per night (USD)
VRBO
From $649 per night (USD)
Expedia
New Home - Heart of Williamstown 183
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Your Dream Home in Williamstown, MA! Nestled in the heart of picturesque Williamstown, this brand-new, modern ...
From $649 per night (USD)
Expedia
From $352 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 $352 per night (USD)
VRBO
From $908 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 $908 per night (USD)
Expedia
From $216 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 $216 per night (USD)
VRBO
Click For Pricing
Expedia
family friendly retreat condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to this adorable apartment in Pittsfield. This cozy space features 1 bedroom with a comfortable queen bed, a ful ...
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Expedia
From $352 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 $352 per night (USD)
VRBO
From $351 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 $351 per night (USD)
Expedia
From $352 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 $352 per night (USD)
VRBO
From $352 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 $352 per night (USD)
Expedia
From $352 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 $352 per night (USD)
VRBO
From $352 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 $352 per night (USD)
Expedia
From $325 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 $325 per night (USD)
VRBO
From $352 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 $352 per night (USD)
Expedia
From $447 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 $447 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 $228 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 $228 per night (USD)
VRBO
From $505 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 $505 per night (USD)
Expedia
From $153 per night (USD)
VRBO
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)
VRBO
From $194 per night (USD)
Expedia
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)
Expedia
From $1161 per night (USD)
VRBO
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)
VRBO
From $381 per night (USD)
Expedia
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 ...
From $381 per night (USD)
Expedia
$Spacious & Family-Ready Home w\/ Fenced Yard in Lee$
From $551 per night (USD)
VRBO
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 $551 per night (USD)
VRBO
From $203 per night (USD)
Expedia
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 $203 per night (USD)
Expedia
From $97 per night (USD)
VRBO
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 $97 per night (USD)
VRBO
From $82 per night (USD)
Expedia
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 $82 per night (USD)
Expedia
From $144 per night (USD)
VRBO
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 $144 per night (USD)
VRBO
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Expedia
Berkshire Mountain Lodge
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Berkshire Mountain Lodge The Berkshires is a cultural art haven that is home to attractions like American author Edith W ...
Click For Pricing
Expedia
From $492 per night (USD)
VRBO
Relaxing Mountaintop Retreat in the Northern Berkshires
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Sitting atop the former Chickley Alps, this magical home is nestled between a XC Ski resort and conservation land. The ...
From $492 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Lakeside Berkshire's Escape
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to one of the best lakeside spots in The Berkshires! This spacious house features a stunning private dock perfec ...
From $433 per night (USD)
Expedia
From $556 per night (USD)
VRBO
Valley Vista atop Jug End
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect getaway in the Berkshires! Nestled beside Jug End Reservation and the Appalachian Trail, this mo ...
From $556 per night (USD)
VRBO
From $1039 per night (USD)
VRBO
Luxurious, Family Friendly, Nature Retreat at Meadows Edge!
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Welcome to Meadows Edge! A charming 3 bedroom (plus 1BR guest suite) home nestled in the heart of the Berkshires that sl ...
From $1039 per night (USD)
VRBO
From $262 per night (USD)
VRBO
Peaceful Mountain Cabin in the Berkshires
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
ENJOY A MOUNTAIN ADVENTURE! You will fall in love with this magic cottage nestled within 2 acres of old growth forest. B ...
From $262 per night (USD)
VRBO
From $205 per night (USD)
Expedia
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
My name is Christine and next to my home is a lovely summer cottage. The cottage has two bedrooms, full kitchen and ba ...
From $205 per night (USD)
Expedia
From $307 per night (USD)
VRBO
Charming 3-bedroom house steps from the Red Lion Inn in delightful Stockbridge
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Unwind in Stockbridge in this charming house, under 5 miles from Tanglewood. The house boasts 3 bedrooms and 2 full bat ...
From $307 per night (USD)
VRBO
From $335 per night (USD)
Expedia
Charming 3-bedroom farmhouse in Lenox
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This Lenox house boasts 3 inviting bedrooms, including 2 queen beds and 1 full bed. The peaceful ambiance of this deligh ...
From $335 per night (USD)
Expedia
From $192 per night (USD)
VRBO
Modern Home Overlooking Mt. Greylock, Williamstown!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Brand new home with state of the art construction. Features 1 bedroom, 2 bathrooms, large living space, kitchen with ind ...
From $192 per night (USD)
VRBO
From $455 per night (USD)
Expedia
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Pets Welcome w/ Fee | 5 Tree-Lined Acres | Swings & Hammocks Unplug from city life and retreat to this spacious vacatio ...
From $455 per night (USD)
Expedia
$Fully Renovated Chalet in Amazing Monterey \/ Lake Garfield with Hot Tub$
From $431 per night (USD)
VRBO
Fully Renovated Chalet in Amazing Monterey \/ Lake Garfield with Hot Tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Relax with the whole family at this peaceful and quiet lake retreat (Lake Garfield). Fully renovated home with an open-p ...
From $431 per night (USD)
VRBO
From $592 per night (USD)
Expedia
Modern Luxury Log Cabin near Ski Butternut in Great Barrington
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Beautiful log cabin located in the heart of the Berkshires less than 2 miles from Butternut Ski Area. This 4 bedroom 3 b ...
From $592 per night (USD)
Expedia
From $412 per night (USD)
VRBO
Lovely Downtown Lenox apt, walk to everything!
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Experience the best of the Berkshires in a beautiful, spacious apartment right in the center Lenox. This updated space i ...
From $412 per night (USD)
VRBO
$Stylish 5 bed\/5 bath Hilltop Manor + Cottage - Amazing location!! 4mi Tanglewood$
From $1272 per night (USD)
Expedia
Stylish 5 bed\/5 bath Hilltop Manor + Cottage - Amazing location!! 4mi Tanglewood
Bedrooms:
5
Bathrooms:
5
Sleeps:
11
Just minutes to Tanglewood! This recently renovated historic homestead in Stockbridge has it all: a Revolutionary-era 4- ...
From $1272 per night (USD)
Expedia
$Pretty Farmhouse 4 bed\/3.5 ba with Gorgeous Kitchen and Big Porch - close to GB!$
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VRBO
Pretty Farmhouse 4 bed\/3.5 ba with Gorgeous Kitchen and Big Porch - close to GB!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This house is perfect for family getaways. The gourmet kitchen boasts a *gorgeous* 4-oven AGA, the king of British count ...
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VRBO
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Expedia
Beautiful 2 Bedroom in the Berkshires at Oak N Spruce Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2-bedroom villa in The Berkshires, Massachusetts! This unit is located in the perfect position for day trips to Albany, ...
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Expedia
From $950 per night (USD)
VRBO
Bright & beautiful lakefront retreat. 5 minute walk to Tanglewood!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
3BR/2.5BA Sun-filled interiors: soaring ceilings & walls of windows frame surrounding forrest. 5-min walk to Tanglewood. ...
From $950 per night (USD)
VRBO
From $603 per night (USD)
Expedia
Waterfront Cottage Retreat By Evergreen Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This lakefront cottage offers year-round magic—whether you're soaking up the summer sun, admiring vibrant fall foliage, ...
From $603 per night (USD)
Expedia
From $272 per night (USD)
VRBO
4 Mi to Great Barrington: Berkshires Retreat!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Peaceful Location | Modern Upgrades w/ Vintage-Inspired Touches | Family Movie/Board Game Nights Four seasons of fun aw ...
From $272 per night (USD)
VRBO
From $377 per night (USD)
Expedia
Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Spacious 4BR, 3.5BA Lakeside Retreat on Lake Ashmere Welcome to your perfect Berkshires getaway—a beautifully appointed ...
From $377 per night (USD)
Expedia
Click For Pricing
VRBO
Light-filled Carpenter's Cottage in 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 ...
Click For Pricing
VRBO

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Berkshire Area Rentals

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Results: 949 Rentals