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 $421 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 $421 per night (USD)
VRBO
From $524 per night (USD)
VRBO
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 $524 per night (USD)
VRBO
$Luxe Berkshires Ski Retreat w\/ Fireplace, King Bed, Chef's Kitchen, Washer\/Dryer$
From $335 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 $335 per night (USD)
VRBO
From $137 per night (USD)
Expedia
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)
Expedia
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VRBO
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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VRBO
From $263 per night (USD)
Expedia
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)
Expedia
From $440 per night (USD)
VRBO
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 $440 per night (USD)
VRBO
$Berkshires Summer Chalet w\/ Pool + Private Hiking Trails$
From $835 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 $835 per night (USD)
VRBO
From $182 per night (USD)
VRBO
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)
VRBO
From $238 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 $238 per night (USD)
VRBO
From $567 per night (USD)
VRBO
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 $567 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 $256 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 $256 per night (USD)
VRBO
From $814 per night (USD)
VRBO
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 $814 per night (USD)
VRBO
From $571 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 $571 per night (USD)
VRBO
$345 Cozy Stay! 1.5 Miles to Pontoosuc Lake \n$
From $440 per night (USD)
Expedia
345 Cozy Stay! 1.5 Miles to Pontoosuc Lake \n
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The perfect place for those seeking peace and quiet and lovers of nature and beautiful spaces. Easy access to all things ...
From $440 per night (USD)
Expedia
From $641 per night (USD)
VRBO
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 $641 per night (USD)
VRBO
From $484 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 $484 per night (USD)
Expedia
From $602 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 $602 per night (USD)
VRBO
From $566 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 $566 per night (USD)
Expedia
From $670 per night (USD)
VRBO
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)
VRBO
From $373 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 $373 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
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
$Ski Jiminy Pk Xmas Wk Sun-Wed: 3 Nites 12\/22-25; Ski In\/Out @Wyndham Bentley Brk$
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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
$Ski Jiminy Peak Xmas Wk: Fri-Mon 12\/27-30 for 3 Nites; @Wyndham Bentley Brook$
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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 $466 per night (USD)
VRBO
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 $466 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 $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
From $393 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 $393 per night (USD)
Expedia
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)
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 $338 per night (USD)
Expedia
From $232 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 $232 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 $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 $558 per night (USD)
VRBO
Charming Long Pond Vacation Home in the Berkshires
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Lond Pond Road is considered one of the most beautiful and peaceful roads in th Berkshires. It is the perfect location t ...
From $558 per night (USD)
VRBO
$JIMINY PEAK - 2\/14-17, 3 NIGHTS - SLOPE SIDE! SKI IN\/SKI OUT, 2BR DELUX UNIT$
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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, ...
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Expedia
From $352 per night (USD)
VRBO
Club Wyndham Bentley Brook Resort - 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
*** Sanitation/Cleaning Update *** Wyndham resorts have always met the highest standards of cleanliness, and now we are ...
From $352 per night (USD)
VRBO
From $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 $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 $351 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 $351 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 $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 $325 per night (USD)
Expedia
Tranquil 2-bedroom house with woodland and pasture views in Great Barrington
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Great Barrington countryside is waiting for you at this 2-bedroom house. Nestled in a serene setting surrounded by conse ...
From $325 per night (USD)
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 $447 per night (USD)
Expedia
Cabin Retreat in the Berkshire Woods
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Hayscent Hollow, where you'll find seclusion and serenity in the Berkshire woods. Featuring 3 bedroo ...
From $447 per night (USD)
Expedia
From $279 per night (USD)
VRBO
Oak n' Spruce Resort in the Berkshires. Charming 2-bedroom in quaint Lee
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the Berkshires at Oak n' Spruce Resort in Lee. Amenities include indoor and outdoor pools, tennis courts, 18-hole ...
From $279 per night (USD)
VRBO
From $228 per night (USD)
Expedia
Immaculate Berkshires home! Close to museums, colleges, and outdoor activities.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Comfortably sleeping 6 with a large yard, screened in porch, and newly renovated bathroom, this charming 3-bedroom house ...
From $228 per night (USD)
Expedia
From $153 per night (USD)
VRBO
Cliffwood Cottage by Evergreen Home
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This charming retreat offers a beautifully designed two-bedroom apartment with a chef’s kitchen, central A/C, washer/dry ...
From $153 per night (USD)
VRBO
From $194 per night (USD)
Expedia
Cozy and conveniently located cottage nestled in the mountains
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to the Cottage at the Barrington House! The Barrington House is nestled in the serene Berkshires Mountains - wh ...
From $194 per night (USD)
Expedia
From $1161 per night (USD)
VRBO
Private estate with heated pool, guest house and incredible views
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
Welcome to the Barrington House! The Barrington House is nestled in the serene Berkshires Mountains - which have long b ...
From $1161 per night (USD)
VRBO
From $381 per night (USD)
Expedia
Bentley Brook 1-BR Mountainside resort sleeps 8- Available April 27-May 3
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
At the base of Jiminy Peak Ski Mountain, this resort is an exceptional choice for mountainside play, and skiing. The are ...
From $381 per night (USD)
Expedia
$Spacious & Family-Ready Home w\/ Fenced Yard in Lee$
From $551 per night (USD)
VRBO
Spacious & Family-Ready Home w\/ Fenced Yard in Lee
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Indulge in the ultimate getaway and experience comfort, style, and convenience in our enchanting home. Step into an open ...
From $551 per night (USD)
VRBO
From $203 per night (USD)
Expedia
Bentley Brook the perfect home base for exploring nearby Berkshire County
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Ski-in and Ski-out your front door! Bentley Brook is situated right at the base of Jiminy Peak Ski Mountain, making this ...
From $203 per night (USD)
Expedia
From $97 per night (USD)
VRBO
Bentley Brook the perfect home base for exploring nearby Berkshire County
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Ski-in and Ski-out your front door! Bentley Brook is situated right at the base of Jiminy Peak Ski Mountain, making this ...
From $97 per night (USD)
VRBO
From $82 per night (USD)
Expedia
Bentley Brook the perfect home base for exploring nearby Berkshire County
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Ski-in and Ski-out your front door! Bentley Brook is situated right at the base of Jiminy Peak Ski Mountain, making this ...
From $82 per night (USD)
Expedia
From $144 per night (USD)
VRBO
Deluxe Queen Room with 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to this charming hotel in Lee. This awesome property features 1 soothing bedroom with a queen bed, perfect for a ...
From $144 per night (USD)
VRBO
From $205 per night (USD)
Expedia
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
My name is Christine and next to my home is a lovely summer cottage. The cottage has two bedrooms, full kitchen and ba ...
From $205 per night (USD)
Expedia
From $307 per night (USD)
VRBO
Charming 3-bedroom house steps from the Red Lion Inn in delightful Stockbridge
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Unwind in Stockbridge in this charming house, under 5 miles from Tanglewood. The house boasts 3 bedrooms and 2 full bat ...
From $307 per night (USD)
VRBO
From $335 per night (USD)
Expedia
Charming 3-bedroom farmhouse in Lenox
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This Lenox house boasts 3 inviting bedrooms, including 2 queen beds and 1 full bed. The peaceful ambiance of this deligh ...
From $335 per night (USD)
Expedia
From $192 per night (USD)
VRBO
Modern Home Overlooking Mt. Greylock, Williamstown!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Brand new home with state of the art construction. Features 1 bedroom, 2 bathrooms, large living space, kitchen with ind ...
From $192 per night (USD)
VRBO
From $455 per night (USD)
Expedia
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Pets Welcome w/ Fee | 5 Tree-Lined Acres | Swings & Hammocks Unplug from city life and retreat to this spacious vacatio ...
From $455 per night (USD)
Expedia
$Fully Renovated Chalet in Amazing Monterey \/ Lake Garfield with Hot Tub$
From $431 per night (USD)
VRBO
Fully Renovated Chalet in Amazing Monterey \/ Lake Garfield with Hot Tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Relax with the whole family at this peaceful and quiet lake retreat (Lake Garfield). Fully renovated home with an open-p ...
From $431 per night (USD)
VRBO
From $592 per night (USD)
Expedia
Modern Luxury Log Cabin near Ski Butternut in Great Barrington
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Beautiful log cabin located in the heart of the Berkshires less than 2 miles from Butternut Ski Area. This 4 bedroom 3 b ...
From $592 per night (USD)
Expedia
From $412 per night (USD)
VRBO
Lovely Downtown Lenox apt, walk to everything!
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Experience the best of the Berkshires in a beautiful, spacious apartment right in the center Lenox. This updated space i ...
From $412 per night (USD)
VRBO
$Stylish 5 bed\/5 bath Hilltop Manor + Cottage - Amazing location!! 4mi Tanglewood$
From $1272 per night (USD)
Expedia
Stylish 5 bed\/5 bath Hilltop Manor + Cottage - Amazing location!! 4mi Tanglewood
Bedrooms:
5
Bathrooms:
5
Sleeps:
11
Just minutes to Tanglewood! This recently renovated historic homestead in Stockbridge has it all: a Revolutionary-era 4- ...
From $1272 per night (USD)
Expedia
From $433 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 $433 per night (USD)
VRBO
From $556 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 $556 per night (USD)
Expedia
From $1039 per night (USD)
VRBO
Luxurious, Family Friendly, Nature Retreat at Meadows Edge!
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Welcome to Meadows Edge! A charming 3 bedroom (plus 1BR guest suite) home nestled in the heart of the Berkshires that sl ...
From $1039 per night (USD)
VRBO
From $908 per night (USD)
Expedia
Contemporary Berkshire Home with Views of Taconic Golf Course
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Discover peace and beauty at this one of a kind Berkshire home designed by Maya Lin (Vietnam Memorial Wall Architect). ...
From $908 per night (USD)
Expedia
From $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
From $216 per night (USD)
VRBO
Bentley Brook 1-bedroom Mountainside ski resort in charming Hancock sleeps 8
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
At the base of Jiminy Peak Ski Mountain, this resort is an exceptional choice for mountainside play, and skiing. The are ...
From $216 per night (USD)
VRBO
From $505 per night (USD)
VRBO
New Custom Home Meets Nature’s Splendor in This Stunning Berkshires Retreat
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
A masterpiece of contemporary design, this new custom-built home is a harmonious blend of modern luxury and nature’s spl ...
From $505 per night (USD)
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
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 $188 per night (USD)
Expedia
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)
Expedia
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 $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

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