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 $319 per night (USD)
VRBO
Cozy Monterey Home w/ Porch: Walk to Lake Garfield
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover historic attractions and unbeatable outdoor recreation at this Monterey vacation rental featuring a stone patio ...
From $319 per night (USD)
VRBO
From $619 per night (USD)
Expedia
Spacious Victorian in N. Adams-walk to Mass MoCA
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Built in 1881, this historic, grand Victorian home is located in the heart of the Berkshires in North Adams, Massachuset ...
From $619 per night (USD)
Expedia
From $503 per night (USD)
VRBO
Cheerful 3-bedroom cottage with woodstove
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20 ...
From $503 per night (USD)
VRBO
From $519 per night (USD)
Expedia
The Freckled Hen's Berkshire Nest
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
My home is a sweet, cozy, private, and very clean farmhouse style Cape in the safe, and quiet neighborhood of Abbey Cour ...
From $519 per night (USD)
Expedia
From $376 per night (USD)
VRBO
Restored 1881 Farm House
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Summary: Beautifully renovated 1881 farm house minutes from down town Lenox. The Space: Quintessential Lenox Farmhouse ...
From $376 per night (USD)
VRBO
From $307 per night (USD)
VRBO
Romantic weekend getaway for two! featuring a fireplace and hot tub,
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
A romantic weekend away! featuring a fire place and hot tub. Enjoy our charming, king sized, super comfy 1-bedroom g ...
From $307 per night (USD)
VRBO
From $705 per night (USD)
VRBO
* Private Berkshire Escape* Monthly Pricing Avail
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: Private home offering relaxation with a beautiful property. This cozy home will give you the comfort you need ...
From $705 per night (USD)
VRBO
From $376 per night (USD)
Expedia
Charming Apartment In Berkshire Victorian Home
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
3rd Floor Penthouse Unit (3 bed/ 1.5 bath). This charming apartment is located in the heart of Pittsfield's Historical D ...
From $376 per night (USD)
Expedia
From $748 per night (USD)
VRBO
Lovely Home on Golden Hill
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Summary: "We are located in the heart of America's cultural epicenter known as the Berkshires. Known as the "Gatehouse" ...
From $748 per night (USD)
VRBO
From $1180 per night (USD)
Expedia
A Grand property in Historic Stockbridge
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
The Taggart House is an grand estate in the heart of The Berkshires. The property is a 5-minute walk to the center of St ...
From $1180 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Completely Renovated Historic Home in the Heart of the Berkshires
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Our home was completely renovated in 2017. The fully equipped kitchen opens to the dining area where the table seats 6, ...
From $357 per night (USD)
VRBO
From $537 per night (USD)
Expedia
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Summary: Right on the mountain, this spacious 2000 sq. ft. retreat Condo is your home away from home. It's the best way ...
From $537 per night (USD)
Expedia
From $356 per night (USD)
VRBO
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Take a trip to this 4-bed, 3-bath vacation rental in Sandisfield, MA! Hidden between the Sandisfield and Otis State Fore ...
From $356 per night (USD)
VRBO
From $229 per night (USD)
VRBO
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Bring your loved one or best friend along on a Berkshires getaway to this rustic 1-bedroom, 1-bath vacation rental in Ne ...
From $229 per night (USD)
VRBO
From $255 per night (USD)
VRBO
'The Mill River Cabin’ w/ Fireplace & River View!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Reconnect with Mother Nature at this 2-bedroom, 1-bath cabin loaded with character! Minutes from the Historic Mill River ...
From $255 per night (USD)
VRBO
From $229 per night (USD)
Expedia
Berkshire Village Carriage House - Super Private!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Private, unique getaway in the center of the Berkshires. We're a 3 minute walk to the Ashuwillticock rail trail. Situat ...
From $229 per night (USD)
Expedia
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VRBO
LAKE FRONT LAKE BUEL Monterey New Marlborough 10 M GREAT BARRINGTON PRIVATE DOCK
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
SATURDAY TO SATURDAYS 10 MINUTES TO GREAT BARRINGTON. A SLICE OF HEAVEN. PRIVATE CUL DE SAC LAKEFRONT INCREDIBLE VIEWS. ...
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VRBO
From $359 per night (USD)
VRBO
Tranquil 3 BR Stockbridge House w/ Private Deck!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house! Boasting a private dec ...
From $359 per night (USD)
VRBO
From $414 per night (USD)
VRBO
Walk to Town/Lake, ’25 Renovation!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Easy & comfortable living on “The Hill” of Great Barrington. Our welcoming space has lots of personal touches, ...
From $414 per night (USD)
VRBO
From $414 per night (USD)
Expedia
19th c. Barn in the Berkshires
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Mason Hill Farm is a celebration of everything we love about the Berkshires. Mountain views, a rushing swimmable brook, ...
From $414 per night (USD)
Expedia
From $480 per night (USD)
VRBO
Stockbridge Bowl Lake Community
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Charming new construction home located in neighborhood community that has a private beach on the Stockbridge Bowl. Just ...
From $480 per night (USD)
VRBO
From $1043 per night (USD)
Expedia
Beautiful Berkshire Farm House on 160+ Acres
Bedrooms:
4
Bathrooms:
7
Sleeps:
16
Don't hesitate reach out about availability even if dates look unavailable. We are happy to review avails with you. A w ...
From $1043 per night (USD)
Expedia
From $673 per night (USD)
VRBO
Massachusetts Lake House w/ Dock - Pets Welcome!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
150’ Lakefront | Renovated | Great for Anglers Tucked along the shores of Lake Buel — a 192-acre mountain lake — this N ...
From $673 per night (USD)
VRBO
From $539 per night (USD)
Expedia
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
New 3 BR rustic-yet-elegantly modern 2400 sq ft country castle on 3+ secluded acres in Manor Lane, a private compound of ...
From $539 per night (USD)
Expedia
$Wildlife Lakeside Cottage\nbeautiful views, amazing wildlife, great location$
From $350 per night (USD)
VRBO
Wildlife Lakeside Cottage\nbeautiful views, amazing wildlife, great location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Light and bright defines the newly renovated cabin boasting spectacular wood throughout and freshly decorated rooms. Ra ...
From $350 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Secluded Mountaintop Retreat in the Heart of the Berkshires
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This secluded 6 acre property is just a 3 minute drive to the village of West Stockbridge. The house is set back from th ...
From $349 per night (USD)
Expedia
From $351 per night (USD)
VRBO
Lovely ranch home getaway in The Berkshires- just 6 miles to Tanglewood
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
This ranch home is in the heart of The Berkshires of Western Massachusetts, in the small town of Richmond. (West Stockbr ...
From $351 per night (USD)
VRBO
From $248 per night (USD)
Expedia
Peace and quiet on the lake
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
OPEN FOR ALL THE WONDERFUL SEASONS! You will love the peaceful and private lake and have plenty of other great things t ...
From $248 per night (USD)
Expedia
From $549 per night (USD)
VRBO
Lakeside Berkshires Home Near Hiking & Skiing!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Escape to the Berkshires for a peaceful mountain respite at this charming, rustic 3-bedroom, 2-bath lakeside home. Choos ...
From $549 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Berkshire Lake at the Pillow, and EV!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
At the intersection of New York. CT and MA, enjoy a newly finished Four Season Home with your own boat dock. Included 2 ...
From $385 per night (USD)
Expedia
From $434 per night (USD)
VRBO
Perfect Holiday Retreat, Completely Renovated, Central Location
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Our completely renovated farmhouse is set upon a hilltop overlooking downtown Lee. It is a perfect spot for culture, sp ...
From $434 per night (USD)
VRBO
From $360 per night (USD)
VRBO
Walk to Dining: Downtown Lenox Guest House!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Steps to Main Street | 2 Mi to Tanglewood | Private Yard w/ Grill This Lenox vacation rental places you in the heart of ...
From $360 per night (USD)
VRBO
From $224 per night (USD)
VRBO
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: You want to pop out of bed, walk outside, and be right on the mountain This 1BR 1 BA Ground Floor Unit Charmin ...
From $224 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Charming historic cottage on scenic road to Mt. Greylock
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room scho ...
From $223 per night (USD)
Expedia
From $192 per night (USD)
VRBO
Apartment in Gorgeous Stonybrook Farm
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This apartment is located in a renovated barn on a large private estate, centrally located in the heart of the Berkshire ...
From $192 per night (USD)
VRBO
From $959 per night (USD)
Expedia
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Bright and airy, cathedral ceiling, Post & Beam home situated in the heart of the Berkshires, minutes from Lenox, Tangle ...
From $959 per night (USD)
Expedia
From $293 per night (USD)
VRBO
North Getaway Cottage
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
A great place for vacationers and those seeking a remote work or school location with three work areas and a guest print ...
From $293 per night (USD)
VRBO
From $1064 per night (USD)
Expedia
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
In 2016 Smithsonian Magazine deemed Great Barrington, "The Best Small Town in America." Manor Lane is a private French C ...
From $1064 per night (USD)
Expedia
From $596 per night (USD)
VRBO
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
The lakeside house is built on a 1.1 acre lot with view of Lake Garfield. It is only a few minutes walk to the town's b ...
From $596 per night (USD)
VRBO
From $384 per night (USD)
Expedia
IN/OUT SKIING CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
2BEDROOM and 2 BATH CONDO. Master Bath has large whirlpool tub. also has full sized pull out couch and portable cribs a ...
From $384 per night (USD)
Expedia
From $157 per night (USD)
VRBO
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This cozy rustic studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built ...
From $157 per night (USD)
VRBO
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Expedia
Lovely two bedroom river-view rental unit
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Comfortable, contemporary-styled, second-floor apartment with a view of the river. You'll have a great time relaxing ins ...
Click For Pricing
Expedia
From $369 per night (USD)
VRBO
Private Berkshires Getaway Minutes to Ski Butternut
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Newly renovated 4 bedroom and 2 full bath home set back from the road is a peaceful oasis. 2 minute drive to Ski Buttern ...
From $369 per night (USD)
VRBO
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Expedia
Berkshire Get away
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Beautiful old home in Lee Massachusetts. Two bedrooms one bath on a quiet street in Lee Massachusetts. A front porch to ...
Click For Pricing
Expedia
From $214 per night (USD)
VRBO
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring ...
From $214 per night (USD)
VRBO
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Expedia
Great mountain getaway
Bedrooms:
3
Bathrooms:
6
Sleeps:
8
Berkshire getaway, close to all activites. Easily accessible first floor. Master on main floor. Fully furnished two base ...
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Expedia
From $478 per night (USD)
VRBO
Best of the Berkshires with Mt. Views, Museums, Paddling, Hiking & On the Water!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Windsor Cottage is a relaxing, lakeside retreat located on Windsor Lake in North Adams, MA where you will enjoy your own ...
From $478 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Berkshire Mountain Escape: family retreat open now for fall color and skiing!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
<b>Your Cozy Berkshires Getaway Awaits!</b> Escape to the serene beauty of the Berkshires! Nestled in a peaceful, fami ...
From $349 per night (USD)
Expedia
From $402 per night (USD)
VRBO
Country Living just minutes from Everything!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
2 minutes to Bartlett's Apple Orchard, Richmond 5 minutes to Bousquet Ski Area, Pittsfield 6 minutes to Balderdash Cella ...
From $402 per night (USD)
VRBO
From $239 per night (USD)
Expedia
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: You want to pop out of bed, walk downstairs, and be right on the mountain This 1BR 1 BA Ground Floor Unit righ ...
From $239 per night (USD)
Expedia
From $281 per night (USD)
VRBO
Hearts Desire is a furnished whole house in a small, colorful garden center.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Newly renovated, one level house with 2 rooms with king sized beds, 1 queen size sleeper sofa. Fully furnished kitchen ...
From $281 per night (USD)
VRBO
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Expedia
Great house in Stockbridge
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Three bedroom house, one en suite on first floor(can be twin or king), two (both queen) on second floor sharing a bathro ...
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Expedia
From $349 per night (USD)
VRBO
UNIQUE - 1BR Country Condo @ Jiminy Peak
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Come and enjoy this increditable country decor. Soak up this country cottage charm while sipping your coffee or tea with ...
From $349 per night (USD)
VRBO
From $261 per night (USD)
Expedia
5 Minutes from Catamount Ski Area
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Cozy house conveniently located in a quiet area near the village of South Egremont. Fresh air, natures beauty all togeth ...
From $261 per night (USD)
Expedia
From $372 per night (USD)
VRBO
Heart of Lenox Walk to Town Cozy Cottage!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
***WE HAVE 220+, 5-STAR REVIEWS ON AIRBNB*** The cottage is a 2-minute walk to Church St., right in the heart of Lenox. ...
From $372 per night (USD)
VRBO
From $132 per night (USD)
Expedia
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Newly renovated unit with fireplace in main room, bathroom, bedroom (queen) and kitchenette.The unit also has a futon th ...
From $132 per night (USD)
Expedia
From $202 per night (USD)
VRBO
2 Bedroom newly renovated townehouse, beautifully decorated at Garfield House
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Garfield House Vacation living for short or longer stays in a newly renovated townhouse is in close proximity to all Ber ...
From $202 per night (USD)
VRBO
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Expedia
2 Bedroom/2 Bath Vacation Rental in the Berkshires
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy the tranquility and comfort of a four-season country getaway. This newly renovated luxury vacation rental is house ...
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Expedia
From $291 per night (USD)
VRBO
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Come and enjoy the many adventures and activities that The Berkshires in Massachusetts has to offer. This cute 2 bedroo ...
From $291 per night (USD)
VRBO
From $383 per night (USD)
VRBO
Two Blocks from the Red Lion Inn & next to Berkshire Theater
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
My place is close to Stockbridge center, Berkshire Theaters, Great Barrington, Lenox, and the Berkshires in general - gr ...
From $383 per night (USD)
VRBO
From $307 per night (USD)
VRBO
Cozy Berkshire cottage with fireplace.
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Relax at this unique, tranquil getaway. Minutes from all the Berkshires' offer; Tanglewood, Bousquet and Jiminy Peak sk ...
From $307 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Spacious waterfront Berkshire home family private get-away
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This renovated waterfront home offers incredible views. Big Pond is surrounded by dense forests and abuts state park lan ...
From $315 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Elegant 19th Century New England 2BR vacation rental at Garfield House
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This super comfortable and spacious Berkshires getaway is located on Main St. in Lee, Massachusetts. The main level has ...
From $225 per night (USD)
VRBO
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Expedia
Two Bedroom house in the heart of the Berkshires
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Two bedrooms, living room-dinning room combo, and full kitchen with all you need for your stay. There is a full-sized be ...
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Expedia
From $494 per night (USD)
VRBO
Picturesque Cottage with Sunroom on Ashmere Lake!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Dive into the rich culture, adventure, and beauty of the Berkshires with this Lake Ashmere vacation rental cottage! Insi ...
From $494 per night (USD)
VRBO
From $574 per night (USD)
Expedia
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Your Home Away from Home: Ski-In/Ski-Out Luxury at Jiminy Peak Welcome to our family’s cozy retreat at Jiminy Peak Ski ...
From $574 per night (USD)
Expedia
From $644 per night (USD)
VRBO
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This hotel/resort is at the base of the ski lift for Jiminy Mountain. And, when you are not on the slopes, it features a ...
From $644 per night (USD)
VRBO
From $469 per night (USD)
Expedia
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Bedrooms:
2
Bathrooms:
1
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 $469 per night (USD)
Expedia
From $384 per night (USD)
VRBO
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
This ski-in, ski-out condo is located right at the base of the mountain in JJ’s Lodge in the heart of the village at Jim ...
From $384 per night (USD)
VRBO
From $286 per night (USD)
Expedia
Artist's Camp on Lake Mahkeenac
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Refurbished cottage, perfect for a couples getaway. This retreat is tastefully decorated with with local antiques & fres ...
From $286 per night (USD)
Expedia
From $734 per night (USD)
VRBO
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This hotel/resort is at the base of the ski lift for Jiminy Mountain. And, when you are not on the slopes, it features a ...
From $734 per night (USD)
VRBO
From $303 per night (USD)
Expedia
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Lakefront property with own dock on Otis Reservoir with beautiful views and garden. Great for fall foliage. For ski sea ...
From $303 per night (USD)
Expedia
From $352 per night (USD)
VRBO
Dancing Horse Lodge
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Dancing Horse Lodge is located on Horse Farm in the heart of the beautiful Berkshire Mountains with plenty of room for f ...
From $352 per night (USD)
VRBO
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Expedia
Full Week of Ski-in,Ski-out @ Jiminy Peak Club Whyndam Bently Brook in Berkshire
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Full week rental only, Feb. 18 (in at 3pm) to Feb 25(check out 11am) @ Club Whyndham Bently Brook Resort @ Jiminy Peak ...
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Expedia
From $359 per night (USD)
VRBO
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Situated in the heart of the Berkshires, this 3-bed, 2-bath vacation rental offers a modern living space, a large yard a ...
From $359 per night (USD)
VRBO
From $502 per night (USD)
Expedia
Modern Victorian Walk to Main Street
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Lovely 4 bedroom, sleeps 10. 3-story classic Victorian home in family-friendly neighborhood. Clean modern interiors and ...
From $502 per night (USD)
Expedia
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VRBO
Park Model Single Family double lofted private heaven on a pond
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
You can't beat this place for location. It is close to all things Berkshires - Tanglewood, Close to Apalachian trail, L ...
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VRBO
From $219 per night (USD)
VRBO
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Fireplace | Grill | Board Games & Puzzles Nestled in the woods of East Otis, this 2-bedroom, 1-bathroom vacation rental ...
From $219 per night (USD)
VRBO
From $706 per night (USD)
VRBO
Perfect for Winter Skiing!!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Perfect family home for all Winter activities with 4 Bedrooms and 3.5 baths, plus it is central to all the cultural act ...
From $706 per night (USD)
VRBO
From $457 per night (USD)
Expedia
Beautiful Timber Frame Home in the Berkshires /Available for Long Term
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The house is a newly constructed cruck timber frame designed by Jack Soban made from naturally treated local pine with c ...
From $457 per night (USD)
Expedia
From $582 per night (USD)
VRBO
Just a min from Downtown Stockbridge on 11 Acres
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: "Feels good staying here! We built this house with our own hands. We chose materials and a design that we loved ...
From $582 per night (USD)
VRBO
From $1266 per night (USD)
Expedia
General Williams Estate House Lenox/Stockbridge
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
The General Williams house is located 2 miles from Stockbridge Center and 5 miles from Lenox Center. Only 7 miles from ...
From $1266 per night (USD)
Expedia
From $1114 per night (USD)
VRBO
Stunning Modern Home - For Your Graduation Celebration
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Experience the charm of New England at our beautiful House in Williamstown, MA! Our cozy and open space offers a perfect ...
From $1114 per night (USD)
VRBO
From $237 per night (USD)
VRBO
Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This updated vintage 1900 home in North Adams is just a 10 minute walk to MASS MoCA, one of the country's largest contem ...
From $237 per night (USD)
VRBO
From $599 per night (USD)
VRBO
Lakefront Bungalow
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Escape to our lakefront bungalow located on Massachusetts largest recreational lake. Otis Reservoir is ideal for boatin ...
From $599 per night (USD)
VRBO
From $856 per night (USD)
VRBO
Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to Jiminy Peak Mountain Resort in the Berkshire Mountains! Our newly-renovated mountain retreat "The Lazy Bear" ...
From $856 per night (USD)
VRBO
From $286 per night (USD)
VRBO
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Great for outdoor enthusiasts, this 3-bedroom, 2.5-bathroom vacation rental home features a balcony, a deck, a patio, an ...
From $286 per night (USD)
VRBO
From $224 per night (USD)
VRBO
A-Frame Cabin w/ Furnished Deck in Becket!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Built in 1974 | Private Acreage & Scenic Surroundings | Fireside Relaxation | EV Charger Embrace a slower pace of life ...
From $224 per night (USD)
VRBO
From $1259 per night (USD)
VRBO
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
Bedrooms:
4
Bathrooms:
7
Sleeps:
12
Wellspring is a sprawling Berkshire escape with unparalleled views of the surrounding mountains. This gorgeous home has ...
From $1259 per night (USD)
VRBO
From $771 per night (USD)
Expedia
Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Discover a unique getaway in the heart of Stockbridge, Massachusetts, at the historic rectory of St. Joseph's Church. Pe ...
From $771 per night (USD)
Expedia
From $574 per night (USD)
VRBO
Guesthouse Cabin vacation rentals in Berkshire County
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Undermountain Lodge offers an escape to a serene cabin, nestled between pristine natural spring lakes with panoramic mou ...
From $574 per night (USD)
VRBO
$house with view in the berkshires\n$
From $342 per night (USD)
VRBO
house with view in the berkshires\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience the charm of this newly renovated home with a wrap-around deck with seasonal vistas of a lake and mountains. ...
From $342 per night (USD)
VRBO
Click For Pricing
VRBO
Spectacular views and close to Great Barrington.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Main floor bedroom with private bath, 2 car garage, electric vehicle charging, screened porch, pool, and Koi pond with v ...
Click For Pricing
VRBO
From $298 per night (USD)
Expedia
Quiet 3BR Home, Near Tanglewood in Stockbridge
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Modern family home moments from Tanglewood, the Stockbridge Bowl, the Norman Rockwell and Chesterwood Museums. Just a 10 ...
From $298 per night (USD)
Expedia
From $487 per night (USD)
VRBO
Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Introducing Woodland Zen: where modern luxury meets secluded tranquility in the heart of the Berkshires. This sleek, co ...
From $487 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
720 Sq. Ft, 2 Bed, 1 Bath cottage with HOT TUB amongst the forest located in a private, dirt road, lake community with n ...
From $285 per night (USD)
Expedia
$Berkshires Lakefront Gem. Cozy home w/ hiking, swimming & all things cultural!\n$
From $370 per night (USD)
VRBO
Berkshires Lakefront Gem. Cozy home w/ hiking, swimming & all things cultural!\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The perfect getaway for people who want to unwind from the grind of everyday life. Little Robin Lake is located right in ...
From $370 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Berkshires' best! Tanglewood, Jacob's Pillow and 400 feet from a pristine lake
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This newly renovated house in the woods on a private road in Lee is an ideal summer or fall retreat. Our little communit ...
From $349 per night (USD)
Expedia
From $475 per night (USD)
VRBO
Sophisticated and secluded Lenox Mt retreat minutes from Tanglewood. New listing
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this chic Lenox Mountain chalet in picturesque West Stockbridge, just minutes from Tanglewood. In a secluded w ...
From $475 per night (USD)
VRBO
From $565 per night (USD)
Expedia
Lake Haven with new dock and amazing views of Lake Garfield
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax with the whole family at this peaceful lakeside home. Enjoy the lake-facing deck for dining and drinks. Swim/boat/ ...
From $565 per night (USD)
Expedia

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