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 $184 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 $184 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 $566 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 $566 per night (USD)
VRBO
From $463 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 $463 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 $472 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 $472 per night (USD)
Expedia
From $1037 per night (USD)
VRBO
Hancock Village Inn at Jiminy Peak
Bedrooms:
6
Bathrooms:
7
Sleeps:
17
Welcome to the Hancock Village Inn – A Classic Berkshires Escape with Modern Comforts including AC in every room! Wheth ...
From $1037 per night (USD)
VRBO
From $581 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 $581 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 $436 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 $436 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 $4463 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 $4463 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
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Expedia
Berkshires - Charming Lakefront Cottage
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Enjoy the tranquil life at Lake Ashmere. Located in the Berkshires, this cottage boasts a private dock with a paddle boa ...
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Expedia
From $293 per night (USD)
VRBO
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 $293 per night (USD)
VRBO
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Expedia
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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Expedia
From $642 per night (USD)
VRBO
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 $642 per night (USD)
VRBO
$Berkshires Retreat W\/ Sauna by Evergreen Home$
From $363 per night (USD)
Expedia
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 $363 per night (USD)
Expedia
From $751 per night (USD)
VRBO
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 $751 per night (USD)
VRBO
From $618 per night (USD)
Expedia
The Penthouse, Downtown Lenox by Evergreen Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Luxury Awaits... This downtown Lenox 3 BR, 2 BA apartment just underwent a complete renovation with design, comfort, an ...
From $618 per night (USD)
Expedia
$Walk to campus; open concept kitchen\/living;nature trail at end of this quiet st$
From $327 per night (USD)
VRBO
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 $327 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $219 per night (USD)
VRBO
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 $219 per night (USD)
VRBO
From $326 per night (USD)
Expedia
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 $326 per night (USD)
Expedia
From $137 per night (USD)
VRBO
Entire home in Dalton, Massachusetts, United States
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. ...
From $137 per night (USD)
VRBO
From $610 per night (USD)
Expedia
Tanglewood Treasure! A Gracious Retreat in the Heart of the Berkshires
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
One of TWO lovely dwellings for rent on nearly four private acres. See VRBO 3529604 to learn more about our Charming Ber ...
From $610 per night (USD)
Expedia
$Luxe Berkshires Ski Retreat w\/ Fireplace, King Bed, Chef's Kitchen, Washer\/Dryer$
From $338 per night (USD)
VRBO
Luxe Berkshires Ski Retreat w\/ Fireplace, King Bed, Chef's Kitchen, Washer\/Dryer
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A perfect stay in the Berkshires! Just 1.5 miles from downtown Great Barrington and 1 mile from Butternut Ski Area, our ...
From $338 per night (USD)
VRBO
From $437 per night (USD)
Expedia
Baldwin Hill Retreat Guest House
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
In one of the most sought after destinations in New England, located just outside Great Barrington near the top of Baldw ...
From $437 per night (USD)
Expedia
$Berkshires Summer Chalet w\/ Pool + Private Hiking Trails$
From $844 per night (USD)
VRBO
Berkshires Summer Chalet w\/ Pool + Private Hiking Trails
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Nestled in the foothills of East Mountain, just minutes from the center of Great Barrington, this woodsy pine cabin has ...
From $844 per night (USD)
VRBO
From $182 per night (USD)
Expedia
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in history and nature, The Historic Kellogg House, built in 1739, is the third oldest house in the Berkshires. R ...
From $182 per night (USD)
Expedia
From $252 per night (USD)
VRBO
Delightful Stockbridge House, Walk to Town!
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
Within walking distance to Main Street in Stockbridge, 38 Church St. offers a large backyard and gardens which boarder p ...
From $252 per night (USD)
VRBO
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Expedia
Spacious 4 bedroom, big pool & outdoor space. Close for local summer activities!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Less than 2 miles from Williams College, this a great homebase for the upcoming Williams events or other summer events i ...
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Expedia
From $263 per night (USD)
VRBO
Luxury 2 Bedroom 2 Bathroom Loft Apartment In Williamstown With Great Amenities!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Luxury two-bedroom loft apartment for in the prestigious Cable Mills building in Williamstown, Massachusetts. A five-min ...
From $263 per night (USD)
VRBO
From $581 per night (USD)
Expedia
Fully Renovated Jiminy Peak Townhouse, walk to all
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Fully renovated in 2022. On-site at ski mountain Jiminy Peak A-frame townhouse with 4 stories of fun for the whole famil ...
From $581 per night (USD)
Expedia
From $885 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 $885 per night (USD)
VRBO
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Expedia
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
Welcome to Wyndham Bentley Brook, your gateway to the ultimate ski-in, ski-out experience at the majestic Jiminy Peak! N ...
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Expedia
$Your Winter Escape: Wyndham Bentley Brook Ski-In, Ski-Out Bliss at Jiminy Peak!\$
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VRBO
Your Winter Escape: Wyndham Bentley Brook Ski-In, Ski-Out Bliss at Jiminy Peak!\"
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
Experience the ultimate ski-in, ski-out getaway at Wyndham Bentley Brook, nestled in the heart of the Berkshire Mountain ...
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VRBO
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Expedia
Fun on the slopes with pool @Vacation Village Berkshires1.0 miles to Jiminy Peak
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Bring your family at this private unit at the Vacation Village in the Berkshires. Views of the Jiminy Peak Ski Resort sl ...
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Expedia
From $276 per night (USD)
VRBO
Downtown | Waterfront | Walk to Shops
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
★ New to Williamstown? Explore our interactive guidebook. One bedroom with all the bells and whistles! Meticulously upg ...
From $276 per night (USD)
VRBO
From $269 per night (USD)
Expedia
2-Bdr Apt In Town, By the Water
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
★ New to Williamstown? Explore our interactive guidebook. A flight of steps takes you to this stunning 2BDR on the 2nd ...
From $269 per night (USD)
Expedia
From $257 per night (USD)
VRBO
New Studio In Town, By the Water
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
★ New to Williamstown? Explore our interactive guidebook. Charming studio just steps away from shops, restaurants & few ...
From $257 per night (USD)
VRBO
From $717 per night (USD)
Expedia
Charming Cape Cod Home in Prime Berkshire Location – 5 Minutes to Tanglewood
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Stylish Berkshires Retreat: This charming home, nestled in the heart of the Berkshires, awaits your next visit. With 4 b ...
From $717 per night (USD)
Expedia
From $621 per night (USD)
VRBO
Lee Manor Berkshire House for Lasting Memories. 5 Bedrooms. 5 Full Bathrooms.
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
The snow is falling! Welcome to our beautiful Berkshire's retreat, a spacious home where families and friends can gather ...
From $621 per night (USD)
VRBO
From $687 per night (USD)
Expedia
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Summary: Nestled in the Berkshires, this 5-BR family home combines comfort and tranquility. The open floor plan connects ...
From $687 per night (USD)
Expedia
From $459 per night (USD)
VRBO
Lakeside 3-BR Berkshires Residence
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Enjoy this newly renovated 3-BR home nestled along the shores of Long Bow Lake, offering stunning views and dir ...
From $459 per night (USD)
VRBO
From $644 per night (USD)
Expedia
Beautiful Berkshire family home
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
This is a beautiful 5 bedroom Berkshire, post and beam private house nestled in the woods just off the Appalachian trail ...
From $644 per night (USD)
Expedia
From $425 per night (USD)
VRBO
Serene rustic cabin in the Berkshires!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Need a break from city life? Escape to our enchanting private cabin nestled in the woods, where romance and seclusion aw ...
From $425 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Comfortable Berkshires retreat on mtn resort, SISO
Bedrooms:
3
Bathrooms:
12
Sleeps:
12
Once a retreat for an NYC real estate family, this grand yet comfortable place in Jiminy Peak has retained the feel of a ...
From $474 per night (USD)
Expedia
From $635 per night (USD)
VRBO
Serene 3-BR Berkshires Log Cabin
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: This spacious and comfortable 3- BR log cabin is the perfect refuge to gather with family and friends. Set on a ...
From $635 per night (USD)
VRBO
From $593 per night (USD)
Expedia
Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Escape to this superb fully equipped house on our 220 acre lake estate. With 4 bedrooms including 1 queen bed, 3 twin be ...
From $593 per night (USD)
Expedia
From $400 per night (USD)
VRBO
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Enjoy all the Berkshires has to offer from this charming 3BR/2BA home base for up to 10 people just 5 minutes from downt ...
From $400 per night (USD)
VRBO
From $352 per night (USD)
Expedia
Stylish, Centrally Located Berkshires Home-Base
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Attractively renovated 4-BR ranch convenient to cultural attractions, outdoor recreation & the farm-to-table food scene. ...
From $352 per night (USD)
Expedia
From $391 per night (USD)
VRBO
Stockbridge house 17 minutes from Tanglewood. Four bedroom, three bathroom.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Recently built 4-bedroom, 3-bathroom Cape Cod style house set apart from neighbors. Very close to Norman Rockwell museu ...
From $391 per night (USD)
VRBO
$Ski Jiminy Pk Xmas Wk Sun-Wed: 3 Nites 12\/22-25; Ski In\/Out @Wyndham Bentley Brk$
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Expedia
Ski Jiminy Pk Xmas Wk Sun-Wed: 3 Nites 12\/22-25; Ski In\/Out @Wyndham Bentley Brk
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Nestled in the Berkshires of MA, this delightful condo is a true Ski In/Ski Out experience. Bentley Brook Resort offers ...
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Expedia
$Ski Jiminy Peak Xmas Wk: Fri-Mon 12\/27-30 for 3 Nites; @Wyndham Bentley Brook$
Click For Pricing
VRBO
Ski Jiminy Peak Xmas Wk: Fri-Mon 12\/27-30 for 3 Nites; @Wyndham Bentley Brook
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Nestled in the Berkshires of MA, this condo comfortably sleeps 8 with 2 Bdrm and 2 full Baths. The cozy living room feat ...
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VRBO
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Expedia
Jiminy Peak 2 Bedroom 2 Bath Deluxe Condo. Wyndham Bentley Brook
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Club Wyndham Bentley Brook on the slopes of family friendly Jiminy Peak! It is just steps away from the slopes, right n ...
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Expedia
From $970 per night (USD)
VRBO
Stunning 6-BR Country Home 10-min to Catamount
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Summary: Escape to the highlands of the Berkshires on this peaceful, 4-acre lot 10-min to skiing at Catamount and 10-min ...
From $970 per night (USD)
VRBO
From $2552 per night (USD)
Expedia
Expansive Rustic and Modern Berkshires Estate on 66 Acres, Mountain Views,...
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Berkshires Meadow Estate Expansive Rustic and Modern Berkshires Estate on 66 Acres, Mountain Views, Pool, Sauna, Perfec ...
From $2552 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: The most unique Suite in the Berkshires - This gorgeous Disney Themed Hotel Room will bring Stitch, Alice & Mic ...
From $250 per night (USD)
VRBO
$Majestic Mountain Side Sheffield\/Great Barrington\/SKI$
From $582 per night (USD)
Expedia
Majestic Mountain Side Sheffield\/Great Barrington\/SKI
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious 5,100 SQ. FT. Mountain Retreat with Winery History Description: Welcome to your new favorite vacation home ...
From $582 per night (USD)
Expedia
$Black Bear Bungalow, Sheffield\/Great Barrington\/Ski Resorts$
From $200 per night (USD)
VRBO
Black Bear Bungalow, Sheffield\/Great Barrington\/Ski Resorts
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This private Luxurious Guest house will Amaze you, with full kitchen, living area and large bedroom with Luxurious Queen ...
From $200 per night (USD)
VRBO
From $602 per night (USD)
Expedia
Spacious 4-bedroom house with pool access in Great Barrington
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Great Barrington and the beautiful Berkshires await you at this 4-bedroom house. Two ensuite and two more bedrooms with ...
From $602 per night (USD)
Expedia
From $1134 per night (USD)
VRBO
Spacious Historic 9-bedroom Inn in charming Lenox. Equipped with full kitchen.
Bedrooms:
8
Bathrooms:
9
Sleeps:
15
Located on the edge of the Pleasant Valley forestry and built in 1766, The Dewey is your remote sanctuary among the scen ...
From $1134 per night (USD)
VRBO
From $153 per night (USD)
VRBO
Charming 2-bedroom resort in brilliant Hancock with AC, Jetted-Tub, WiFi, Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
16
Escape to a wonderful resort in Hancock for a relaxing getaway. This 2-bedroom retreat features 2 king beds and 2 sofa b ...
From $153 per night (USD)
VRBO
From $428 per night (USD)
VRBO
NEW! Berkshire Bliss. Cheery & comfortable private home in Williamstown Center
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
NEW to VRBO! Absolutely adorable private house in Williamstown just 3 minutes from Spring St,, Clark Art and Williams Co ...
From $428 per night (USD)
VRBO
From $409 per night (USD)
Expedia
1 Mi to Dtwn: Beautiful Home in Williamstown!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private Creek | Pine Cobble Views | Near Hiking Trails | 1 Mi to Williams College Enjoy a well-equipped kitchen, a cozy ...
From $409 per night (USD)
Expedia
From $1341 per night (USD)
VRBO
Spacious Luxury Berkshire's Estate on 21 acres
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
The Fox Hollow Estate is a private 1940s estate home, renovated to modern-day luxury, located in gorgeous Berkshire Coun ...
From $1341 per night (USD)
VRBO
From $488 per night (USD)
Expedia
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Summary: You want to bring your whole family to Jiminy and be in ONE CONDO, with gorgeous views, a deck, BBQ, Backyard, ...
From $488 per night (USD)
Expedia
From $216 per night (USD)
VRBO
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Experience the Magic of the Berkshires in this charming 1BR 1 BA Suite which Sleeps 4 comfortably with its King ...
From $216 per night (USD)
VRBO
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Expedia
Charming 2-bedroom resort in marvelous Hancock with AC, fitness room, WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Escape to a charming resort in Hancock for a peaceful stay located at the base of Jiminy Peak Ski Mountain. This gorgeou ...
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Expedia
From $652 per night (USD)
VRBO
Florida Mountain Log Cabin!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
About this space Have fun and enjoy this calm, stylish custom built log cabin on top of Florida Mountain. Conveniently l ...
From $652 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Historic 1804 house in N Becket Village in the Berkshires
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The North Becket Village historic district has 47 buildings, 35 of which contributed to its architectural and historic l ...
From $235 per night (USD)
Expedia
$JIMINY PEAK - 2\/6-8 & 2\/13-16 2026- SLOPE SIDE! SKI IN\/SKI OUT, 2BR DELUX UNIT$
From $1145 per night (USD)
VRBO
JIMINY PEAK - 2\/6-8 & 2\/13-16 2026- SLOPE SIDE! SKI IN\/SKI OUT, 2BR DELUX UNIT
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in a slope side condo at Jiminy Peak! This charming property features 2 cozy bedrooms with a king and queen bed, ...
From $1145 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 $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 $308 per night (USD)
Expedia
Charming house in Pittsfield with cozy vibes. Next to a reserve and a lake.
Bedrooms:
2
Bathrooms:
1
Sleeps:
5
Located in Pittsfield, this adorable house offers guests a cozy living room with a sofa bed for extra sleeping space. Wi ...
From $308 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: The most fun Suite in the Berkshires - This gorgeous Gamers Suite will bring Families together Like No Other! N ...
From $250 per night (USD)
VRBO
From $232 per night (USD)
Expedia
Serene 2-bedroom apartment in North Adams.Plenty of off street parking.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled in North Adams, this delightful first floor apartment boasts 2 cozy bedrooms - one with a queen bed and the othe ...
From $232 per night (USD)
Expedia
From $316 per night (USD)
VRBO
Bungalow in the Berkshires
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Three bedroom, one bath, fully furnished home located on a tree-lined cul-de-sac in a quiet Lee neighborhood. Bright hom ...
From $316 per night (USD)
VRBO
From $469 per night (USD)
Expedia
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 $469 per night (USD)
Expedia
From $372 per night (USD)
VRBO
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 $372 per night (USD)
VRBO
From $440 per night (USD)
Expedia
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 $440 per night (USD)
Expedia
From $1202 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 $1202 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 $357 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 $357 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 $484 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 $484 per night (USD)
Expedia
$NEW Listing-Fully Renovated Chalet in Amazing Monterey \/ Lake Garfield w\/Hot Tub$
From $647 per night (USD)
VRBO
NEW Listing-Fully Renovated Chalet in Amazing Monterey \/ Lake Garfield w\/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 $647 per night (USD)
VRBO
From $590 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 $590 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 $1089 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 $1089 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

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