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 $218 per night (USD)
VRBO
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Pittsfield at this charming corporate apartment. With AC, a washing machine, and WiFi, guests can enjoy a marv ...
From $218 per night (USD)
VRBO
From $1384 per night (USD)
Expedia
Serene 5-BR Retreat 9-Min to Catamount
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Summary: Gather your friends and family at this a luxurious 5-BR retreat. Nestled in the serene woodlands of the Berkshi ...
From $1384 per night (USD)
Expedia
From $198 per night (USD)
VRBO
Large 3-bedroom house with WiFi and AC in Great Barrington
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located in Great Barrington, this superb house boasts 3 cozy bedrooms - one with a king bed, one with two twin beds, and ...
From $198 per night (USD)
VRBO
$4 Mi to Skiing: Cottage w\/ Fire Pit in Richmond!$
From $256 per night (USD)
Expedia
4 Mi to Skiing: Cottage w\/ Fire Pit in Richmond!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Furnished Outdoor Space | Walk to Richmond Pond | Peaceful Surroundings Your New England escape awaits at this 3-bedroo ...
From $256 per night (USD)
Expedia
From $369 per night (USD)
VRBO
Cozy Condo Near MASS MoCA
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Your Modern Bohemian Retreat in North Adams Experience a blend of contemporary comfort and bohemian charm in ...
From $369 per night (USD)
VRBO
$Steepletop: Nature Lover’s Paradise w\/Rec Room$
From $482 per night (USD)
VRBO
Steepletop: Nature Lover’s Paradise w\/Rec Room
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Welcome to Steepletop Lodge, a beautiful 4 bed/ 2 bath modern retreat with endless opportunities to unplug and ...
From $482 per night (USD)
VRBO
From $543 per night (USD)
VRBO
Chalet des Collines: 5 Mins to Catamount
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Gorgeous country escape set on 2 pastoral acres of a lovely meadow in the Taconic Range. Enjoy mountain biking ...
From $543 per night (USD)
VRBO
From $555 per night (USD)
VRBO
River Cottage: Riverfront Home, Walkable Community
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to River Cottage, a beautifully renovated 3-bedroom, 2-bathroom riverfront gem in the heart of Great Ba ...
From $555 per night (USD)
VRBO
From $366 per night (USD)
VRBO
Meadow Top Cottage: Countryside Cottage on 72 Acres
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Meadow Top Cottage is charming and cozy 3-bed, 2-bath cottage in the quiet hamlet of Mill River, MA. The 72-acr ...
From $366 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Solomon Ely Homestead - Charming Pittsfield Stay
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Enjoy your stay at this 1847 New England farmhouse located just steps from downtown Pittsfield. Make yourself at home wi ...
From $433 per night (USD)
Expedia
From $557 per night (USD)
VRBO
Cozy Home in Lenox
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Enjoy a stylish experience at this cozy newly renovated two-bedroom mobile home in the Berkshires of Lenox, Massachusett ...
From $557 per night (USD)
VRBO
From $838 per night (USD)
Expedia
The Race Mountain House
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
High on the slopes of Race Mountain, this spacious 4-bedroom villa offers sweeping east-facing views. In the early hours ...
From $838 per night (USD)
Expedia
From $389 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 $389 per night (USD)
VRBO
From $340 per night (USD)
VRBO
Berkshire Blue House - sleeps 6!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Berkshire getaway! This 3-bedroom house sleeps 6. It has 2 bathrooms and a large deck. Two of the spacious bedrooms h ...
From $340 per night (USD)
VRBO
From $484 per night (USD)
VRBO
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 $484 per night (USD)
VRBO
From $602 per night (USD)
Expedia
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 $602 per night (USD)
Expedia
From $566 per night (USD)
VRBO
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 $566 per night (USD)
VRBO
From $670 per night (USD)
Expedia
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Perfect Home for the Holidays! Spacious, comfortable and exceptionally well outfitted kitchen! Plus enjoy all the Berk ...
From $670 per night (USD)
Expedia
From $373 per night (USD)
VRBO
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 $373 per night (USD)
VRBO
From $391 per night (USD)
Expedia
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)
Expedia
From $230 per night (USD)
VRBO
Cozy 1-bedroom condo at ski resort with WiFi, fitness room, pool & hottub
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Relax in a comfortable and cozy space after a winter day on the ski slopes. Enjoy all of the amenities of the on premise ...
From $230 per night (USD)
VRBO
$1 Mi to Dtwn: Cottage w\/ Large Yard in Stockbridge$
From $433 per night (USD)
Expedia
1 Mi to Dtwn: Cottage w\/ Large Yard in Stockbridge
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Dog Friendly w/ Fee | Furnished Deck for Coffee Moments | Fireside Relaxation Nestled in the heart of Stockbridge, with ...
From $433 per night (USD)
Expedia
From $496 per night (USD)
VRBO
Lake Views & Dock Access - Pittsfield Cottage!
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
Waterfront Yard | Furnished Sunroom | Boat Dock | Beach Gear Provided Nestled in the serene town of Pittsfield, 'Pontoo ...
From $496 per night (USD)
VRBO
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Expedia
Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Escape to this peaceful ski in/out 2-bedroom resort retreat in Hancock at Jiminy Peak. Unwind in the welcoming living ro ...
Click For Pricing
Expedia
$Zen Riverfront studio w\/ Spa steam shower, wood stove, SKI Catamount \/Butternut$
From $224 per night (USD)
VRBO
Zen Riverfront studio w\/ Spa steam shower, wood stove, SKI Catamount \/Butternut
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tucked away in Great Barrington, this marvelous, newly renovated, sunny studio features a well equipped kitchenette, a c ...
From $224 per night (USD)
VRBO
From $2606 per night (USD)
VRBO
Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
Welcome to Moose Lodge – A 7,500 Sq. Ft. Berkshires Luxury Retreat Experience the pinnacle of comfort and entertainment ...
From $2606 per night (USD)
VRBO
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VRBO
Cozy 1-bedroom at a New England style resort in the Berkshire mountains
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This amazing 1-bedroom resort in Hancock is perfect for your mountain escape. With a king bed, fireplace, a convenient s ...
Click For Pricing
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
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Expedia
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in the wooded hills of the Berkshire Mountains, this outdoor-oriented resort offers year-round fun. Miles of be ...
Click For Pricing
Expedia
From $226 per night (USD)
VRBO
Deluxe One Bedroom and One Bathroom with Full Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Discover this lovely 1-bedroom gem in Hancock. Featuring a cozy bedroom with a king bed, a bathroom with luxurious ameni ...
From $226 per night (USD)
VRBO
From $196 per night (USD)
VRBO
Deluxe Two Bedroom and Two Bathroom with Full Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover the beauty of Hancock! Beautiful and scenic neighborhood. Enjoy the breath taking views in the 1 king bedroom a ...
From $196 per night (USD)
VRBO
$Woodland Haven w\/ Heated Pool by Evergreen Home$
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Expedia
Woodland Haven w\/ Heated Pool by Evergreen Home
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
Recently renovated, this gorgeous 2BR-3BA home features vaulted ceilings, beautiful wood beams, gorgeous stone fireplace ...
Click For Pricing
Expedia
From $273 per night (USD)
VRBO
Guest House Sanctuary by Evergreen Home
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Beautiful haven in the woods. The 2BR guest house is currently available for up to 5 guests. Surrounded by nature, this ...
From $273 per night (USD)
VRBO
$Berkshires Estate w\/ Heated Pool by Evergreen Home$
From $1273 per night (USD)
Expedia
Berkshires Estate w\/ Heated Pool by Evergreen Home
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Welcome to your own private Berkshires paradise. Located 10 min from downtown Great Barrington or Stockbridge, and 20 mi ...
From $1273 per night (USD)
Expedia
From $385 per night (USD)
VRBO
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Located in Lanesborough, guests love this Cozy Cottage aka “Polly’s Place” for its warmth, central location and accessib ...
From $385 per night (USD)
VRBO
From $388 per night (USD)
Expedia
Cheever Hollow Farm an essential retreat central to Lenox and the Berkshires
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Welcome to Cheeverhollowfarm in picturesque Richmond/Lenox. Please Contact me for specific details or requests. We are ...
From $388 per night (USD)
Expedia
From $237 per night (USD)
VRBO
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!
Bedrooms:
1
Bathrooms:
4
Sleeps:
5
Fenced Backyard | 4 Mi to Downtown Pittsfield | Near Trails & Lakes Experience the natural beauty of the Berkshires whe ...
From $237 per night (USD)
VRBO
From $239 per night (USD)
VRBO
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Bedrooms:
2
Bathrooms:
1
Sleeps:
3
Welcome to the Mt. Williams Retreat—a centrally located guesthouse just two blocks from Williams College. Designed for g ...
From $239 per night (USD)
VRBO
From $424 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 $424 per night (USD)
VRBO
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Expedia
Charming Victorian walking distance to Mass MoCa
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The Heron is a spacious 4 bedroom home with 2 full baths and a small, private, fenced-in yard. It was fully redesigned i ...
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Expedia
$Ski Jiminy Pk Xmas Wk Sun-Wed: 3 Nites 12\/22-25; Ski In\/Out @Wyndham Bentley Brk$
Click For Pricing
VRBO
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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VRBO
$Ski Jiminy Peak Xmas Wk: Fri-Mon 12\/27-30 for 3 Nites; @Wyndham Bentley Brook$
Click For Pricing
Expedia
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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Expedia
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VRBO
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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VRBO
From $945 per night (USD)
Expedia
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 $945 per night (USD)
Expedia
From $2320 per night (USD)
VRBO
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 $2320 per night (USD)
VRBO
From $232 per night (USD)
Expedia
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 $232 per night (USD)
Expedia
$Majestic Mountain Side Sheffield\/Great Barrington\/SKI$
From $560 per night (USD)
VRBO
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 $560 per night (USD)
VRBO
$Black Bear Bungalow, Sheffield\/Great Barrington\/Ski Resorts$
From $213 per night (USD)
Expedia
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 $213 per night (USD)
Expedia
From $602 per night (USD)
VRBO
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)
VRBO
From $1144 per night (USD)
Expedia
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 $1144 per night (USD)
Expedia
From $299 per night (USD)
VRBO
The Hideaway: Berkshire Home - Village of Egremont
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our home in the village of Egremont (part of Great Barrington). Both the house and property are open and inv ...
From $299 per night (USD)
VRBO
From $576 per night (USD)
VRBO
The Maple House - Modern Retreat Near Town
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Summary: You will enjoy your stay at The Maple House, a beautifully restored mid-century modern retreat in the Berkshire ...
From $576 per night (USD)
VRBO
From $3804 per night (USD)
VRBO
Winthrop Estate - 1925 Charm & Modern Luxury
Bedrooms:
11
Bathrooms:
12
Sleeps:
24
Summary: I’m Jamie, the proud caretaker of the timeless and beautiful Winthrop Estate. This restored 1920s Gilded Age ma ...
From $3804 per night (USD)
VRBO
From $1254 per night (USD)
Expedia
New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
We have been renting out the Taggart House estate for over 10 years. The "guest house" has always been our primary home ...
From $1254 per night (USD)
Expedia
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 $538 per night (USD)
VRBO
Brand New Barn House
Bedrooms:
6
Bathrooms:
3
Sleeps:
6
The story of this house is so cool! But first ... This *brand new* barn house with woods, meadow, and stream sits on 3 a ...
From $538 per night (USD)
VRBO
From $393 per night (USD)
VRBO
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 $393 per night (USD)
VRBO
From $1296 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 $1296 per night (USD)
VRBO
From $338 per night (USD)
VRBO
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 $338 per night (USD)
VRBO
From $232 per night (USD)
Expedia
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 $232 per night (USD)
Expedia
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VRBO
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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VRBO
From $652 per night (USD)
Expedia
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)
Expedia
From $188 per night (USD)
VRBO
Entire cottage in Berkshire Villiage
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
With close access to the Ashuwillticook rail trail and a short drive to convenient shopping and restaurants, this is a p ...
From $188 per night (USD)
VRBO
From $232 per night (USD)
Expedia
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 $232 per night (USD)
Expedia
From $229 per night (USD)
VRBO
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 $229 per night (USD)
VRBO
From $316 per night (USD)
Expedia
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)
Expedia
From $509 per night (USD)
VRBO
Spacious 4-bedroom house in peaceful Southfield with AC, WiFi and more!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Nestled in Southfield, this delightful house offers four bedrooms, including a king bed, two queen beds, a crib, and a f ...
From $509 per night (USD)
VRBO
From $475 per night (USD)
VRBO
Stockbridge Snug- cabin luxury just steps to lake!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Snug (an energy efficient home) was designed, renovated, and completed in June 2022. It serves as a cozy haven of re ...
From $475 per night (USD)
VRBO
From $420 per night (USD)
VRBO
Berkshire Mountain retreat with Urban eco-luxuries
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comfo ...
From $420 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Welcome to your mountain retreat, perfectly situated in Hancock's premier ski resort, Jiminy Peak. This beautifully appo ...
From $293 per night (USD)
Expedia
$Family-Friendly Mountain Retreat at Jiminy Peak, ski on\/off, fitness, pool\n\n$
From $229 per night (USD)
VRBO
Family-Friendly Mountain Retreat at Jiminy Peak, ski on\/off, fitness, pool\n\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Create unforgettable memories in this charming, one-bedroom, one-bathroom rental, perfectly located right on the mountai ...
From $229 per night (USD)
VRBO
From $328 per night (USD)
Expedia
Airy Upstate Getaway with a View
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your perfect getaway in New Lebanon! This open and spacious home offers stunning views of the New Lebanon Val ...
From $328 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Cozy Family Cottage in Peaceful New Marlborough
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Birdwatcher's Paradise! Experience acres of unspoiled wilderness as far as you can see while being surrounde ...
From $268 per night (USD)
VRBO
From $415 per night (USD)
Expedia
Family Ski House at Catamount !
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience the ultimate family ski getaway at this spacious 4-bedroom, 3-bath home across from Catamount Ski Area. With ...
From $415 per night (USD)
Expedia
From $355 per night (USD)
VRBO
A Writer's Retreat at The Barn
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to a renovated barn that blends rustic charm with modern comfort. Enjoy airy, open spaces with vaulted ceilings a ...
From $355 per night (USD)
VRBO
From $274 per night (USD)
Expedia
Rustic 3bd Lake Front Country Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Take a step out of everyday life and enjoy some rest and relaxation at this cozy home on the lake nestled in the hills o ...
From $274 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Bougie B’s Mountainside Getaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to our updated 2-bedroom, 2-bath condo at Jiminy Peak! Perfectly situated for the ski season, you'll enjoy quick ...
From $280 per night (USD)
VRBO
$- Lake Front 4 Bdr w\/ Fast Internet! -$
From $502 per night (USD)
Expedia
- Lake Front 4 Bdr w\/ Fast Internet! -
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Take a step out of busy life and enjoy this large well curated lake front property in the heart of The Berkshires. Ente ...
From $502 per night (USD)
Expedia
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VRBO
The Eddy - Apres Ski Sanctuary
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to The Eddy, a stylish retreat in the hills of The Berkshires, just a stone's throw from Otis Ridge! This home ...
Click For Pricing
VRBO
From $583 per night (USD)
Expedia
Spacious 4Bd Just a Block from Lake Mansfield!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Charming four bedroom house on the hill with convenient access to downtown Great Barrington. Just a few blocks to the b ...
From $583 per night (USD)
Expedia
From $516 per night (USD)
VRBO
Charming 3-BR Berkshires Timber Cottage
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Gather your family and friends and experience the charm of this 3-BR cabin in Becket, MA. Featuring three bedro ...
From $516 per night (USD)
VRBO
From $673 per night (USD)
VRBO
Condo Resort at Jiminy Peak Ski Mountain's Base
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Enjoy great year round activities from white water rafting and hiking in the summer, to skiing at the famous Jiminy Peak ...
From $673 per night (USD)
VRBO
From $151 per night (USD)
VRBO
Beautiful 2-bedroom apartment in New Lebanon
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to this apartment in picturesque New Lebanon. This cozy retreat features 2 bedrooms with a queen and full bed, a ...
From $151 per night (USD)
VRBO
From $346 per night (USD)
VRBO
Monterey, MA. Near Tanglewood, Charming rustic farm house, well equipped kitchen
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Air conditioned. Situated on 11 acres, totally private, surrounded by apple orchard, open fields and bordering woods. N ...
From $346 per night (USD)
VRBO
From $514 per night (USD)
VRBO
Charming 3-bedroom chic farmhouse within walking distance of great barrington
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Your cozy getaway awaits in Great Barrington at this marvelous farmhouse. With 3 bedrooms including 2 queen beds and 2 t ...
From $514 per night (USD)
VRBO
From $510 per night (USD)
Expedia
Pet Friendly Oasis on 5 Private Acres, 10 min to Tanglewood
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Escape to this peaceful retreat on 5 private acres. Large picture windows envelope you in the gorgeous surroundings, and ...
From $510 per night (USD)
Expedia
From $645 per night (USD)
VRBO
Spacious 4BR Central-Berkshires Home with POOL!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Spacious and comfortable home in a serene setting and ideal location. Whether you are coming for performing arts, museu ...
From $645 per night (USD)
VRBO
$Available February 17-21 2025. Sleep 8 - 2-bed apt on Jiminy Peak. Ski in\/out!$
From $564 per night (USD)
Expedia
Available February 17-21 2025. Sleep 8 - 2-bed apt on Jiminy Peak. Ski in\/out!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Available February 17-21 - President’s week 2025! Condo Resort at Jiminy Peak Ski Mountain's Base Enjoy ski retreat at ...
From $564 per night (USD)
Expedia
From $432 per night (USD)
VRBO
Yacca House NEW Serene Retreat in Canaan
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to Yacca House, a serene wellness retreat in Canaan, NY. This thoughtfully designed space accommodates up to 8 gu ...
From $432 per night (USD)
VRBO
$JIMINY PEAK - 2\/14-17, 3 NIGHTS - SLOPE SIDE! SKI IN\/SKI OUT, 2BR DELUX UNIT$
Click For Pricing
Expedia
JIMINY PEAK - 2\/14-17, 3 NIGHTS - 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, ...
Click For Pricing
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 $308 per night (USD)
VRBO
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)
VRBO
From $436 per night (USD)
Expedia
Spacious Farmhouse with Stunning Views
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
The Eugene House was built in 1940 on the grounds of Abby Lodge farm, a historic summer estate across from Herman Melvil ...
From $436 per night (USD)
Expedia
From $229 per night (USD)
VRBO
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 $229 per night (USD)
VRBO
$Golf, Swim & Ski: Gem w\/ Lake Access in Pittsfield$
From $291 per night (USD)
Expedia
Golf, Swim & Ski: Gem w\/ Lake Access in Pittsfield
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
4 Seasons of Fun | Near Outdoor Activities | Movie Nights at Home Get back to nature at this 2-bedroom, 2-bath Pittsfie ...
From $291 per night (USD)
Expedia
From $181 per night (USD)
VRBO
Charming Lakeview Cottage in Heart of the Berkshires
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Relax in your island cottage overlooking beautiful Onota Lake in the heart of the Berkshires. Take in 180 degree pristin ...
From $181 per night (USD)
VRBO
From $335 per night (USD)
VRBO
Sunny 2-bed House in Downtown Lenox with WiFi and AC, Kitchenette
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This gem is perfectly situated on a quiet residential street in historic downtown Lenox. Take a short 3 minute walk to t ...
From $335 per night (USD)
VRBO

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