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 $768 per night (USD)
VRBO
Beautiful Farm House Near Family Ski Mountains And Other Fun Winter Activities
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This gorgeous farmhouse has four bedrooms each with a private full bathroom. Each bedroom has a queen size bed, sitting ...
From $768 per night (USD)
VRBO
From $491 per night (USD)
VRBO
Dock on Lake Garfield, 10 min to Butternut, Wifi, So Fun!
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
RENOVATED Charm: 1920's cottage with 3 acres of natural surroundings. A short, 5 minute walk via nature trail and stai ...
From $491 per night (USD)
VRBO
From $643 per night (USD)
VRBO
Modern 4 bedroom lakefront house in The Berkshires.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
4 Bedroom lakefront house on beautiful Richmond Pond. All new kitchen appliances and bathrooms. Just steps from our bran ...
From $643 per night (USD)
VRBO
From $285 per night (USD)
VRBO
Berkshires Living!! Beautiful Location, Breathtaking Sunsets, Fully Reno Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Enjoy your own private summer mountaintop in the Berkshires - Two story, completely renovated air conditioned home on ...
From $285 per night (USD)
VRBO
From $208 per night (USD)
VRBO
Renting for 31+ days; Competitive pricing, Cozy, Scenic, Quiet, area.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
We want renters to be comfortable, so we have been particularly careful during the pandemic regarding cleaning and by p ...
From $208 per night (USD)
VRBO
From $417 per night (USD)
VRBO
Berkshire lake house on lake Garfield, Monterey MA; private, 5 BR, sleeps 12
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Family vacation lake house on lake Garfield, Monterey MA. Beautiful lake location nestled in the hills of the Berkshires ...
From $417 per night (USD)
VRBO
From $235 per night (USD)
VRBO
Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This beautiful gem has been lovingly cared for by our family for almost 20 years—and has served as a relaxing retreat al ...
From $235 per night (USD)
VRBO
From $586 per night (USD)
VRBO
Berkshire Lake Beauty-Modern Amenities On The Lake
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
This home has been 100% remodeled! With a beautiful spot directly on Lake Pontoosuc, the new kitchen, bathrooms, firepla ...
From $586 per night (USD)
VRBO
From $247 per night (USD)
VRBO
Rustic Waterfront Retreat With Private Dock, 2 kayaks & canoe. Air conditioner!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This A-frame cottage has private waterfront access with two single kayaks and a canoe. A new 12,000 btu air conditoner k ...
From $247 per night (USD)
VRBO
From $451 per night (USD)
VRBO
Beautiful four season lakeside log home close to all Berkshires attractions.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Very comfortable and private log home on a non motor lake. West facing (beautiful sunsets over the lake). Three bedrooms ...
From $451 per night (USD)
VRBO
From $503 per night (USD)
VRBO
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
One of a kind must see getaway. Berkshire Glamour meets Hollywood Rennaisance and Town & Country. This well-lit, newly r ...
From $503 per night (USD)
VRBO
From $205 per night (USD)
VRBO
Lake Community - Near Town, Attractions
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A short drive from New York City or Boston, or a flight into Hartford or Albany and you're in a new world of peacefulnes ...
From $205 per night (USD)
VRBO
$Berkshires \/ Great Barrington Chic & Cozy, Sleeps 10$
From $596 per night (USD)
VRBO
Berkshires \/ Great Barrington Chic & Cozy, Sleeps 10
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
*20% month-long and 10% week-long discount automatically applied* An inspiring renovated historic home with chic and th ...
From $596 per night (USD)
VRBO
From $397 per night (USD)
VRBO
In town 2 bedroom, one bath carriage barn. Sleeps 5.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Beautiful two bedroom, one bath carriage barn with balcony. Features a living room with cathedral ceilings, dining area ...
From $397 per night (USD)
VRBO
From $411 per night (USD)
VRBO
Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This two bedroom condo in the Mountainside area is one of the most luxurious and appealing places to stay at Jiminy Peak ...
From $411 per night (USD)
VRBO
From $288 per night (USD)
VRBO
Romantic Berkshires Cottage - Stunning Views, Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This unique cottage--30' away from our home on a fenced, three-acre property--has its own entrance and its own parking s ...
From $288 per night (USD)
VRBO
From $380 per night (USD)
VRBO
Vacation in a Berkshire Farmhouse
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
Welcome to our idyllic farmhouse in the beautiful Berkshires, where you’ll enjoy the tranquility and comfort of country ...
From $380 per night (USD)
VRBO
From $377 per night (USD)
VRBO
A Charming Mid 1800's Stockbridge Farmhouse.
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Transform yourself in to the middle of a Norman Rockwell painting. It is easy to see how so many of his paintings were i ...
From $377 per night (USD)
VRBO
From $681 per night (USD)
VRBO
Lenox, private setting, close to Tanglewood
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beautifully furnished, well-located Lenox home has a brand new kitchen ! Central Air Conditioning, a King bed in b ...
From $681 per night (USD)
VRBO
From $269 per night (USD)
VRBO
A roomy remodeled retreat close to MassMoCA
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Large Victorian house within walking distance to MassMOCA and downtown North Adams. Sleeps eight comfortably with two ba ...
From $269 per night (USD)
VRBO
From $1141 per night (USD)
VRBO
Stunning Renovated Victorian
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Located in the beautiful Berkshires, MA, the 5000 sqf home is located in a desired neighborhood known as "the Hill.” The ...
From $1141 per night (USD)
VRBO
From $371 per night (USD)
Expedia
Bershire Home Rental: Enjoy Berkshire Fall Foliage
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Beautiful house in rural northern Berkshire County. Property sits on 8 acres of land, 4 acres mowed and maintained. Tw ...
From $371 per night (USD)
Expedia
From $452 per night (USD)
VRBO
Stockbridge Village Cottage With Mountain View’s and walk to town
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Old meets new in this lovely cottage, a short walk to the Red Lion Inn. Lots of light, comfortable furniture, beautiful, ...
From $452 per night (USD)
VRBO
From $384 per night (USD)
VRBO
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
Bedrooms:
3
Bathrooms:
5
Sleeps:
6
A Writer’s Haven!!! 360-degree scenic PRIVACY. YET… just 1/2 mile off the Mass Pike and 15 minutes from Tanglewood, Len ...
From $384 per night (USD)
VRBO
From $153 per night (USD)
VRBO
Studio Loft in the Berkshires
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Loft-at-Sea is a 800 Sq. Ft open floor plan studio apartment with plenty of light from three skylights and a picture win ...
From $153 per night (USD)
VRBO
From $620 per night (USD)
VRBO
Beautiful Home in AMAZING Berkshire Location
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Come nestle in the woods at this beautiful retreat in a PRIME location - 5 minutes to both downtown Lee and Stockbridge, ...
From $620 per night (USD)
VRBO
From $354 per night (USD)
VRBO
Lovely Townhouse In Heart Of Lenox
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Just steps from our historical town, enjoy a special location in our quiet family neighborhood. Lenox offers gourmet res ...
From $354 per night (USD)
VRBO
From $547 per night (USD)
VRBO
Location Location! Comfort and Privacy So Close to Downtown
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Extraordinary privacy and convenience just a 10-minute walk to Main Street. You don't have to choose between privacy a ...
From $547 per night (USD)
VRBO
From $1165 per night (USD)
VRBO
Hang By The Pool or Walk To Town
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Available Friday June 28th - Friday July 12th '24. Heated pool, gourmet kitchen and a short walk to town. Restored to i ...
From $1165 per night (USD)
VRBO
From $496 per night (USD)
VRBO
Huge Designer House on 2 acres property, minutes to restaurants, museums
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Huge 3 bedroom 2 bath designer house sitting on 2 acres land in Lenox. Three hours from NYC and two from Boston. All mus ...
From $496 per night (USD)
VRBO
From $399 per night (USD)
VRBO
Timberdoodle-a mountainside treehouse
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CATAMOUNT SKI RESORT IS ON THE OTHER SIDE OF THE MOUNTAIN. 11 MILES TO SKI BUTTERNUT. HIGH SPEED FIBER OPTIC INTERNET ...
From $399 per night (USD)
VRBO
From $243 per night (USD)
VRBO
Converted Berkshire schoolhouse on a quiet river
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Renovated schoolhouse on a quiet river in the Berkshires. This is the perfect place to unwind. Great for families and fr ...
From $243 per night (USD)
VRBO
From $507 per night (USD)
VRBO
Secluded Family Home in Serene Stockbridge Woods
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
***WE ALSO HAVE 31 5-STAR REVIEWS ON AIRBNB*** ***NEW SUMMER DATES NOW OPEN*** Private Forest Retreat | Heart of the B ...
From $507 per night (USD)
VRBO
From $305 per night (USD)
VRBO
Renovated Colonial on the River! Fantastic Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Blue House on the Bend Built around 1820, the Blue House on the Bend, an historic eyebrow colonial located on an idyl ...
From $305 per night (USD)
VRBO
$Ashmere Lake Log Cabin with privacy \/ 2 Bedrooms\/ 3 night minimum$
From $242 per night (USD)
VRBO
Ashmere Lake Log Cabin with privacy \/ 2 Bedrooms\/ 3 night minimum
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Brand new log cabin. Charming, quiet with privacy. If peace and tranquility are one of your vacation objectives, then th ...
From $242 per night (USD)
VRBO
From $453 per night (USD)
VRBO
Twin Maple Farm: Charming Modern Farmhouse
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This updated 1920s farmhouse centrally located in the Berkshires is great for family vacations with a large backyard for ...
From $453 per night (USD)
VRBO
From $264 per night (USD)
VRBO
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Swiss chalet type house with exposed douglas fir beams. Back of home has all windows opening to deck and forest. 2 bedro ...
From $264 per night (USD)
VRBO
From $177 per night (USD)
VRBO
Ashmere Lakefront Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Second floor one bedroom/ one bathroom apartment overlooking Lake Ashmere Docks and Lake . Enjoy kayaking or paddle boar ...
From $177 per night (USD)
VRBO
From $393 per night (USD)
VRBO
Newly Renovated Home With All The Modern Amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
The perfect spot for a Berkshire getaway! This renovated home has all the old charm while offering a comfortable modern ...
From $393 per night (USD)
VRBO
From $353 per night (USD)
Expedia
Large duplex near MASSMoCA, MCLA (21)
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This gorgeous late 19th century Victorian duplex recently under went a complete renovation. Situated on a lovely quiet s ...
From $353 per night (USD)
Expedia
From $338 per night (USD)
VRBO
Stockbridge Vacation by Norman Rockwell
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This 1900 farmhouse in the village of Stockbridge offers all the convenience of walking to restaurants, shops, the Red L ...
From $338 per night (USD)
VRBO
$Cozy Accommodations w\/ Fireplace, Full Kitchen & More!$
From $300 per night (USD)
VRBO
Cozy Accommodations w\/ Fireplace, Full Kitchen & More!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located on the resort property: At Mountainside, Village Center, Country Village, or Beaver Pond. Ideal for larger famil ...
From $300 per night (USD)
VRBO
$Spacious, Family-Friendly Getaway w\/ Full Kitchen & Fireplace$
From $378 per night (USD)
VRBO
Spacious, Family-Friendly Getaway w\/ Full Kitchen & Fireplace
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Located on the resort property: At Mountainside, Village Center, or Country Village, Ideal for larger families and grou ...
From $378 per night (USD)
VRBO
$Comfy Suite in the Berkshires w\/ WiFi & Great Resort Amenities!$
From $201 per night (USD)
VRBO
Comfy Suite in the Berkshires w\/ WiFi & Great Resort Amenities!
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
So much, So Close - Nestled in the Berkshires, a getaway to Jiminy Peak offers everything you need, so close to home. Sp ...
From $201 per night (USD)
VRBO
From $242 per night (USD)
VRBO
Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This 2BR home can sleep up to ...
From $242 per night (USD)
VRBO
From $214 per night (USD)
VRBO
Unique Condo, Quiet Neighborhood, Walk to Town.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Two bedroom, two bathroom condominium in a two family house located in one of Lenox’s most convenient and quiet neighbor ...
From $214 per night (USD)
VRBO
From $257 per night (USD)
VRBO
Quiet Lake house with beautiful water views
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Massachusetts lake house on beautiful Ashmere lake in the Berkshires. Living room and porch provide beautiful views of t ...
From $257 per night (USD)
VRBO
From $281 per night (USD)
Expedia
Perfect Vacation Get Away - Historical New Marlborough
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Quaint cottage in Southern Berkshire nestled in the historic district of New Marlborough. Cottage sits on 3 acres all o ...
From $281 per night (USD)
Expedia
From $700 per night (USD)
VRBO
Wyndham Bentley Brook at Jiminy Peak ski in ski out
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Jiminy Peak Ski in/ski out in Winter. Summer activities at Jiminy Peak in the Berkshires. Fully equipped kitchen, living ...
From $700 per night (USD)
VRBO
$Wyndham Bentley Brook Jiminy Peak ski in\/out unit$
From $600 per night (USD)
VRBO
Wyndham Bentley Brook Jiminy Peak ski in\/out unit
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Jiminy Peak Ski in/ski out in Winter. Summer activities at Jiminy Peak in the Berkshires. Fully equipped kitchen, livin ...
From $600 per night (USD)
VRBO
From $210 per night (USD)
VRBO
Retreat In The Woods
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This lovely home is located in a quiet corner of the northern Berkshires. It is located just over a mile from beautiful ...
From $210 per night (USD)
VRBO
$East Otis Vacation Rental w\/ Private Deck & BBQ!$
From $259 per night (USD)
Expedia
East Otis Vacation Rental w\/ Private Deck & BBQ!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Prepare for your Western Massachusetts lake escape by booking this welcoming 1-bathroom studio cottage in East Otis! Loc ...
From $259 per night (USD)
Expedia
$The Studio\nmini home away from home in the Berkshires$
From $132 per night (USD)
VRBO
The Studio\nmini home away from home in the Berkshires
Bedrooms:
1
Bathrooms:
0
Sleeps:
0
The studio is in the front room of an historic house (circa 1830) on Main St, in Lee. convenient to all of the town's a ...
From $132 per night (USD)
VRBO
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Expedia
Ski resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
8
Family oriented ski resort . Many amenities with activities for all age groups .No need to leave the property .Swimming ...
Click For Pricing
Expedia
From $263 per night (USD)
VRBO
Chic Pittsfield Home With A View!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: This true country home has a quirky layout allowing guests to gather in different areas as well as retreat to p ...
From $263 per night (USD)
VRBO
Click For Pricing
Expedia
Architect Designed Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy all the Berkshires has to offer in this Historic South Lee home. Perched on a hillside just across the road from t ...
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Expedia
From $247 per night (USD)
VRBO
Embrace the Berkshires
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Bring the whole family to this great place with lots of room for fun. Jiminy Peak in Hancock, Massachusetts offers exce ...
From $247 per night (USD)
VRBO
From $214 per night (USD)
Expedia
VACATION VILLAGE IN THE BERKSHIRES MA-2 BDRM CONDO
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Professionally decorated in a traditional New England style, Vacation Village in the Berkshires offers spacious suites w ...
From $214 per night (USD)
Expedia
$Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On\/Off Country Inn Redone$
From $232 per night (USD)
VRBO
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On\/Off Country Inn Redone
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: You want to pop out of bed, walk outside, and be right on the mountain - this is the place for you. This 1BR, ...
From $232 per night (USD)
VRBO
From $472 per night (USD)
VRBO
Berkshires Lake View, Hot Tub, Large Open Great Room, Lrg Kitchen
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Families, couples, remote workers, and skiers, your Berkshires vacation rental search stops here! Bluescape is your plac ...
From $472 per night (USD)
VRBO
From $620 per night (USD)
VRBO
Waterfront oasis in heart of Berkshires
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This waterfront retreat offers total privacy and spa-like serenity. Steps from a private pond, it's also minutes from ev ...
From $620 per night (USD)
VRBO
From $517 per night (USD)
Expedia
Hupi House - A Peaceful, Wooded, Lakeside Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Nestled into more than 8 acres of pristine, private forest above the northwest section of Lake Garfield in Mont ...
From $517 per night (USD)
Expedia
Click For Pricing
VRBO
Beautiful Spacious Berkshire A-Frame Mountain House
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
The house is conveniently located near arts venues (Tanglewood, Jacobs Pillow, Becket Arts Center), shopping centers (Le ...
Click For Pricing
VRBO
From $170 per night (USD)
Expedia
Cozy Renovated with 1 parking space
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
1 Bedroom, 1 bath with 1 off-street parking space. Cozy renovated unit features western and eastern exposures, eat in ki ...
From $170 per night (USD)
Expedia
From $353 per night (USD)
VRBO
Escape to your cozy retreat near Pontoosuc Lake and Jiminy Peak
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
In the center of Lanesborough lies a cozy 2-bedroom house that provides a peaceful escape for your upcoming trip. Imagin ...
From $353 per night (USD)
VRBO
From $448 per night (USD)
Expedia
Tranquil 3-BR Waterfront Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Retreat to the tranquility and calm of this newly-renovated lakeside chalet in the Berkshires. The home is perf ...
From $448 per night (USD)
Expedia
Click For Pricing
VRBO
WEEKEND FUN 1BEDROOM
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
DVD Player Television Wi-Fi Internet Access Hairdryer Washer/Dryer In Unit Balcony/Patio Wyndham Bentley Brook. Locate ...
Click For Pricing
VRBO
$Center of Lenox, cozy 2-bedroom apartment <br>REVIEWS https:\/\/abnb.me\/kcBk7oCR6xb$
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Expedia
Center of Lenox, cozy 2-bedroom apartment <br>REVIEWS https:\/\/abnb.me\/kcBk7oCR6xb
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
READ OUR AIRBNB REVIEWS https://abnb.me/kcBk7oCR6xb CHECK OUT THE ADJACENT 2 BEDROOM APARTMENT ALSO AVAILABLE: https: ...
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Expedia
From $1093 per night (USD)
VRBO
Amore Estate - beautiful room with many places to explore and relax in.
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
Fully renovated and decor updated in 2024! 8 acre property, shared with one carriage house not rented, with amazing vie ...
From $1093 per night (USD)
VRBO
Click For Pricing
Expedia
Cozy Condo with resort amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Resort offers multiple pools, hot tub, sauna, exercise room, locker rooms with showers, wireless internet throughout ...
Click For Pricing
Expedia
From $256 per night (USD)
VRBO
Fun Filmmaker's Bungalow wPool & Pro Screening Room
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Hollywood Bungalow in the Berkshires is a cool cozy rustic country bungalow featuring a screening room with incredible ...
From $256 per night (USD)
VRBO
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Expedia
Slopeside View: Airy, Luxury Condo with Pool. Minutes from it all!
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Experience the wonder of waking up to the majestic beauty of Bousquet Mountain. With the ability to walk onto the mounta ...
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Expedia
From $216 per night (USD)
VRBO
Lovely bright apartment in pastoral shaker barn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Berkshire living at its best! This historic shaker barn on 2 open acres has three apartments. Rent one or more for your ...
From $216 per night (USD)
VRBO
From $603 per night (USD)
VRBO
1780 Colonial Hilltop Manor - Amazing location
Bedrooms:
8
Bathrooms:
4
Sleeps:
9
Just minutes to Tanglewood! This Revolutionary-era home sits on a 10-acre hill with views of Monument Mountain, lawn, wo ...
From $603 per night (USD)
VRBO
$Lakefront Otis Home w\/ Stunning Views & Boats!$
From $538 per night (USD)
VRBO
Lakefront Otis Home w\/ Stunning Views & Boats!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Escape to this light-infused retreat filled with art and nestled on 6 wooded acres. Revel in captivating views of Hayes ...
From $538 per night (USD)
VRBO
From $473 per night (USD)
Expedia
Luxury Vacation Rental in the Berkshires!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Known for its thriving art institutions, outdoor activities, fall foliage, world-class museums, and renowned annual fest ...
From $473 per night (USD)
Expedia
From $223 per night (USD)
VRBO
Vacation Rental Home in the Berkshires!
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Head to the Northern Berkshires to experience world-class museums, a plethora of outdoor activities, fall foliage, a far ...
From $223 per night (USD)
VRBO
From $140 per night (USD)
Expedia
7 nights in our 1 br, full kitchen villa. Only 110 per night
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Available for the last week of July. 320 beautiful acres at the foot or Beartown State Forest, Oak 'n Spruce offers plen ...
From $140 per night (USD)
Expedia
From $274 per night (USD)
VRBO
Lake, Tennis, Beach Access, Skiing, Kayaking, Fishing
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This peaceful and centrally-located place is close proximity to many Berkshire attractions for an idea getaway. This hom ...
From $274 per night (USD)
VRBO
From $506 per night (USD)
Expedia
Mason's Lodge · Luxury Home - 3 Fireplaces Mins to Ski & Town
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our cozy Berkshires retreat, located just a stone's throw away from downtown Great Barrington and minutes to ...
From $506 per night (USD)
Expedia
From $1035 per night (USD)
VRBO
Hancock Village Inn at Jiminy Peak
Bedrooms:
6
Bathrooms:
7
Sleeps:
17
❄️ Your Winter Getaway Awaits at the Historic Hancock Village Inn! 🏔️ Why You'll Love It – Prime Location: Only minute ...
From $1035 per night (USD)
VRBO
From $493 per night (USD)
Expedia
Classic Stockbridge Cottage
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Classic Southern Berkshire escape, built in the early 1900s by a cartographer for the NY Times. The home boast ...
From $493 per night (USD)
Expedia
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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 $375 per night (USD)
Expedia
Spacious Historic Home in the Berkshires!
Bedrooms:
2
Bathrooms:
7
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)
Expedia
From $445 per night (USD)
VRBO
Beautiful Berkshire Lake View and 2.1 Miles from Down Hill Skiing!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Captivating home overlooking Stevens Lake within minutes from Butternut! Private and only a short distance fro ...
From $445 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 $4439 per night (USD)
VRBO
Sunset Falls: A Berkshire Mountain Luxury Retreat
Bedrooms:
9
Bathrooms:
6
Sleeps:
14
Welcome to Sunset Falls, where luxury meets nature in this modern architecturally significant home on 167 private acres. ...
From $4439 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 $246 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 $246 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Charming A-Frame Near all the Best parts of the Berkshires!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Our A-Frame Cabin is the perfect place to disconnect and get away from it all! A family member literally built it by han ...
From $326 per night (USD)
Expedia
Click For Pricing
VRBO
Perfect for Entertaining and Relaxation in the Berkshires!Furnished Country Home
Bedrooms:
4
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 $639 per night (USD)
Expedia
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 $639 per night (USD)
Expedia
$Berkshires Retreat W\/ Sauna by Evergreen Home$
From $336 per night (USD)
VRBO
Berkshires Retreat W\/ Sauna by Evergreen Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Escape the hustle and unwind at this unique, tranquil octagonal retreat in the Berkshires. Set on 14 acres of private wo ...
From $336 per night (USD)
VRBO
From $558 per night (USD)
Expedia
Berkshires Colonial on 2 Acres by Evergreen Home
Bedrooms:
3
Bathrooms:
5
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 $558 per night (USD)
Expedia
From $521 per night (USD)
VRBO
The Penthouse, Downtown Lenox by Evergreen Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
10 MINUTES FROM BOUSQUET MOUNTAIN Luxury Awaits... This downtown Lenox 3 BR, 2 BA apartment just underwent a complete ...
From $521 per night (USD)
VRBO
$Walk to campus; open concept kitchen\/living;nature trail at end of this quiet st$
From $313 per night (USD)
Expedia
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 $313 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $211 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 $211 per night (USD)
Expedia
From $316 per night (USD)
VRBO
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Bedrooms:
2
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 $316 per night (USD)
VRBO
From $869 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 $869 per night (USD)
VRBO

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