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 $144 per night (USD)
VRBO
Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Everyone needs a place to lay their weary head. For travelers visiting Hancock, Wyndham at Bentley Brook is an excellent ...
From $144 per night (USD)
VRBO
From $1049 per night (USD)
Expedia
Hancock Village Inn at Jiminy Peak
Bedrooms:
6
Bathrooms:
7
Sleeps:
17
Discover the ultimate retreat at Hancock Village Inn! Ideal for groups and families of all sizes and ages our expansive ...
From $1049 per night (USD)
Expedia
From $392 per night (USD)
VRBO
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 $392 per night (USD)
VRBO
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Expedia
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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Expedia
From $344 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 $344 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
$Berkshires Retreat W\/ Sauna by Evergreen Home$
From $365 per night (USD)
VRBO
Berkshires Retreat W\/ Sauna by Evergreen Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Escape the hustle and unwind at this unique, tranquil octagonal retreat in the Berkshires. Set on 14 acres of private wo ...
From $365 per night (USD)
VRBO
From $601 per night (USD)
Expedia
Berkshires Colonial on 2 Acres by Evergreen Home
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
A Berkshires grand colonial home, on 2.7 private acres is the perfect home-base for your getaway to the Berkshires. Loc ...
From $601 per night (USD)
Expedia
From $624 per night (USD)
VRBO
The Penthouse, Downtown Lenox by Evergreen Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Luxury Awaits... This downtown Lenox 3 BR, 2 BA apartment just underwent a complete renovation with design, comfort, an ...
From $624 per night (USD)
VRBO
$Walk to campus; open concept kitchen\/living;nature trail at end of this quiet st$
From $285 per night (USD)
Expedia
Walk to campus; open concept kitchen\/living;nature trail at end of this quiet st
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
A private townhouse w/ 3 bedrooms (1 with Queen on main floor, 2 on second floor -King bed and twin bed the two upstairs ...
From $285 per night (USD)
Expedia
From $635 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 $635 per night (USD)
VRBO
$Romantic Boutique Hotel \/ Bed and Breakfast - Smallest Room in The Berkshires$
From $1276 per night (USD)
Expedia
Romantic Boutique Hotel \/ Bed and Breakfast - Smallest Room in The Berkshires
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The smallest room around literally a double bed 2 nightstands and a bathroom, for those traveling light and just need a ...
From $1276 per night (USD)
Expedia
$Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.\n$
From $338 per night (USD)
VRBO
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.\n
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A dream getaway. Perfect for a couple or family. Enjoy a late night swim and or a game of pool in the clubhouse. Wake up ...
From $338 per night (USD)
VRBO
From $288 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 $288 per night (USD)
Expedia
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VRBO
Family friendly house with two complete units, private deck and yard.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This newly remodeled house features two complete units (upstairs and downstairs) with separate entrances and a connectin ...
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VRBO
From $212 per night (USD)
Expedia
Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
New listing ! Looking for a centrally located place to stay? This Berkshires home is 5 minutes from Bousquet Ski Resort ...
From $212 per night (USD)
Expedia
From $715 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 $715 per night (USD)
VRBO
From $439 per night (USD)
VRBO
Gracious Berkshire Retreat
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 $439 per night (USD)
VRBO
$Luxe Berkshires Ski Retreat w\/ Fireplace, King Bed, Chef's Kitchen, Washer\/Dryer$
From $323 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 $323 per night (USD)
VRBO
From $211 per night (USD)
Expedia
Sweet Cozy Victorian in Housatonic. Close to everything.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newl ...
From $211 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 $456 per night (USD)
Expedia
Lee Manor Berkshire House for Lasting Memories. 5 Bedrooms. 5 Full Bathrooms.
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Fall is here and Holidays are coming! Welcome to our beautiful Berkshire's retreat, a spacious home where families and f ...
From $456 per night (USD)
Expedia
$Quiet mountain home w\/ brook; walking distance to Spring street.$
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VRBO
Quiet mountain home w\/ brook; walking distance to Spring street.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful home in the Berkshires within walking distance to Spring street, down in a quiet hollow, and with a sloping ba ...
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VRBO
From $413 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 $413 per night (USD)
Expedia
From $332 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 $332 per night (USD)
VRBO
$Escape to Serenity: Unplug in the Berkshires!\n$
From $892 per night (USD)
Expedia
Escape to Serenity: Unplug in the Berkshires!\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
In our modern world, "unplugging" has never been more important. Vacation Village in the Berkshires offers the perfect l ...
From $892 per night (USD)
Expedia
From $449 per night (USD)
VRBO
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 ...
From $449 per night (USD)
VRBO
$Your Winter Escape: Wyndham Bentley Brook Ski-In, Ski-Out Bliss at Jiminy Peak!\$
From $494 per night (USD)
Expedia
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 ...
From $494 per night (USD)
Expedia
Click For Pricing
VRBO
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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VRBO
From $253 per night (USD)
Expedia
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 $253 per night (USD)
Expedia
From $246 per night (USD)
VRBO
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 $246 per night (USD)
VRBO
From $234 per night (USD)
Expedia
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 $234 per night (USD)
Expedia
$Centrally Located Gorgeous Cape Cod Home for Tanglewood or Shakespeare & Co \n$
From $996 per night (USD)
VRBO
Centrally Located Gorgeous Cape Cod Home for Tanglewood or Shakespeare & Co \n
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Stylish Berkshires Retreat: This charming home, nestled in the heart of the Berkshires, awaits your next visit. With 5 b ...
From $996 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 $542 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 $542 per night (USD)
Expedia
$Prime Berkshires w\/ Pool + Private Hiking Trails$
From $613 per night (USD)
VRBO
Prime Berkshires 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 $613 per night (USD)
VRBO
From $159 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 $159 per night (USD)
Expedia
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 $576 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 $576 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Charming 2-bedroom apartment in downtown Stockbridge with AC, WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience the charm of Stockbridge in this newly renovated 2-bedroom apartment, just steps from the iconic Red Lion Inn ...
From $344 per night (USD)
VRBO
From $288 per night (USD)
Expedia
Oak n’ Spruce Resort in the Berkshires Charming 2-bedroom Villa
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stay comfortably at the Berkshires in our 2-bedroom villa. The bedrooms feature a king bed and a queen bed, and pull out ...
From $288 per night (USD)
Expedia
From $665 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 $665 per night (USD)
VRBO
From $465 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 $465 per night (USD)
Expedia
From $698 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 $698 per night (USD)
VRBO
From $376 per night (USD)
Expedia
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
Enjoy all the Berkshires has to offer from this charming 3BR/2BA home-base in Lenox. Drive 5 minutes to downtown Lenox & ...
From $376 per night (USD)
Expedia
From $360 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 $360 per night (USD)
VRBO
From $391 per night (USD)
Expedia
Stockbridge house 17 minutes from Tanglewood. Four bedroom, three bathroom.
Bedrooms:
3
Bathrooms:
3
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
$Lovely renovated 1810 farmhouse w\/ 4 ensuite bedrooms, pool & river on 15 acres$
From $1089 per night (USD)
VRBO
Lovely renovated 1810 farmhouse w\/ 4 ensuite bedrooms, pool & river on 15 acres
Bedrooms:
6
Bathrooms:
4
Sleeps:
8
If you want the charm of an 1810 New England farmhouse with all the comforts and conveniences of 2024, this is the house ...
From $1089 per night (USD)
VRBO
From $295 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 $295 per night (USD)
VRBO
$Berkshire apt w\/ FAST internet near lake & slopes$
From $259 per night (USD)
VRBO
Berkshire apt w\/ FAST internet near lake & slopes
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
@cornerhousekate welcomes you to this 2nd floor apt overlooking the picturesque town of Monterey from its very own priva ...
From $259 per night (USD)
VRBO
From $447 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 $447 per night (USD)
VRBO
From $199 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 $199 per night (USD)
VRBO
From $259 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 $259 per night (USD)
VRBO
From $130 per night (USD)
VRBO
Studio Condo Outdoor Adventures
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $130 per night (USD)
VRBO
From $130 per night (USD)
VRBO
Studio Condo Outdoor Adventures
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $130 per night (USD)
VRBO
From $130 per night (USD)
VRBO
Studio Condo Outdoor Adventures
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $130 per night (USD)
VRBO
From $127 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $127 per night (USD)
VRBO
From $127 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $127 per night (USD)
VRBO
From $127 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $127 per night (USD)
VRBO
From $127 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $127 per night (USD)
VRBO
From $130 per night (USD)
VRBO
Studio Condo Outdoor Adventures
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $130 per night (USD)
VRBO
From $130 per night (USD)
VRBO
Studio Condo Outdoor Adventures
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $130 per night (USD)
VRBO
$Luxury GB home w\/ heated pool less than 10 min from ski slopes$
From $1073 per night (USD)
VRBO
Luxury GB home w\/ heated pool less than 10 min from ski slopes
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Perfect location for summer, fall foliage, and winter skiing! A recently renovated home on 10 acres less than 10 minutes ...
From $1073 per night (USD)
VRBO
From $377 per night (USD)
VRBO
Family Friendly Raised Cape in the Center of Lenox Village
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This renovated raised cape is in the center of historic Lenox, MA. 3 large bedrooms include: king size bed, full size be ...
From $377 per night (USD)
VRBO
From $519 per night (USD)
VRBO
1 Bedroom Deluxe Condo, Sleeps 8, at Bentley Brook, Jiminy Peak Ski Mountain!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
8
This spacious one-bedroom resort suite measures approximately 780 to 880 square feet. You will enjoy two queen beds in t ...
From $519 per night (USD)
VRBO
From $734 per night (USD)
VRBO
2 Bedroom Deluxe Condo at Bentley Brook, Jiminy Peak Ski Mountain!!
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 $734 per night (USD)
VRBO
$Studio Suite, w\/ Full Kitchen at Bentley Brook, at Jiminy Peak Ski Mountain!!$
From $461 per night (USD)
VRBO
Studio Suite, w\/ Full Kitchen at Bentley Brook, at Jiminy Peak Ski Mountain!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This spacious studio suite measures approximately 400 square feet. You will enjoy one queen Murphy bed and one queen sle ...
From $461 per night (USD)
VRBO
From $314 per night (USD)
VRBO
Berkshire Mountainside Condo
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Fabulous 4 season Berkshire condo rental has room for 9 guests. Ski from this condo to Bousquet Ski Area; enjoy spring r ...
From $314 per night (USD)
VRBO
From $195 per night (USD)
VRBO
Bentley Brook Resort 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
At the base of Jiminy Peak Ski Mountain, Bentley Brook resort is an exceptional choice for mountainside play. The area d ...
From $195 per night (USD)
VRBO
From $105 per night (USD)
VRBO
Fully furnished one-bedroom apartment located just steps from Williams College.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This luxuriously appointed, fully furnished one-bedroom apartment is perfectly located in downtown Williamstown. The apa ...
From $105 per night (USD)
VRBO
From $245 per night (USD)
VRBO
Berkshire Mountain Cottage: in the Heart of the Berkshires
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Berkshire Mountain Cottage is a warm and cozy hideaway located in the Berkshire hills. Its located between North Egremon ...
From $245 per night (USD)
VRBO
From $267 per night (USD)
VRBO
Endearing cottage in the Berkshires, walking distance to downtown and Mass MoCA.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
0.7 miles to MASS MoCA & downtown. Close drive to Williamstown MA & VT. Hiking, museums, and skiing are close by. On-pr ...
From $267 per night (USD)
VRBO
$Serene Renovated Barn w\/ Firepit$
From $218 per night (USD)
Expedia
Serene Renovated Barn w\/ Firepit
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
About this space Minutes from downtown Great Barrington and at the top of a quiet property, this design-forward 1 bed/1 ...
From $218 per night (USD)
Expedia
From $358 per night (USD)
VRBO
Historic Stone Church in The Berkshires
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Hinterland Hall was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Plac ...
From $358 per night (USD)
VRBO
From $376 per night (USD)
VRBO
Clean & Modern space with a mix of original warmth and charming renovation.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to "The Hideaway On Main " in Stockbridge Center. Now booking for 20-29 day stays this summer. Our recently r ...
From $376 per night (USD)
VRBO
From $572 per night (USD)
VRBO
18 Century farmhouse with modern conveniences set on 47 magnificent acres
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Berkshire Farm House rental combining the charm of an original 18 Berkshire with modern conveniences and luxury ameniti ...
From $572 per night (USD)
VRBO
From $476 per night (USD)
VRBO
1840 Village Farmhouse with Modern Comforts
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Three bedrooms (2 queen; 1 single) plus den/guest room with queen-size pull-out couch. Comfortable living/dining area w ...
From $476 per night (USD)
VRBO
From $395 per night (USD)
VRBO
Relax between your Berkshire adventures! Easy walk to town! Centrally located!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Owner operated with pride 😊 Our vacation home in Lee Massachusetts is centrally located to ALL THINGS BERKSHIRES! In th ...
From $395 per night (USD)
VRBO
From $713 per night (USD)
Expedia
Romantic and Secluded Berkshire's Gem
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Beautiful log cabin in the middle of private 5 acres of woods with all of the 21st-century amenities. We are 5 minutes a ...
From $713 per night (USD)
Expedia
From $363 per night (USD)
VRBO
Elegant Lake Buel Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Totally renovated and updated lake house with access to Lake Buel right across the quaint road. Sit on your large screen ...
From $363 per night (USD)
VRBO
From $341 per night (USD)
VRBO
Historic Lenox Village Summer Rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Historic Lenox Village Condo available for summer 2024. Beautifully Furnished. Walking distance to shopping, dining, gro ...
From $341 per night (USD)
VRBO
$Center of Lenox, cozy Apartment 2-bedroom<br>REVIEWS https:\/\/abnb.me\/kcBk7oCR6xb$
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VRBO
Center of Lenox, cozy Apartment 2-bedroom<br>REVIEWS https:\/\/abnb.me\/kcBk7oCR6xb
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
READ OUR AIRBNB REVIEWS https://abnb.me/kcBk7oCR6xb Our two story apartment is spacious and cozy all in one. Built i ...
Click For Pricing
VRBO
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Expedia
Bentley Brook at Jiminy Peak ^ Studio
Bedrooms:
1
Bathrooms:
0
Sleeps:
4
Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski ...
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Expedia
From $324 per night (USD)
VRBO
Historic 1817 Berkshire Farmhouse- Close to Everything!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
View our Superhost reviews here: https://www.airbnb.com/rooms/26598493? preview_for_ml=true&source_impression_id=p3_1675 ...
From $324 per night (USD)
VRBO
From $574 per night (USD)
VRBO
New England Family Home with Hot Tub and Pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Family-Friendly New England style 5 bedroom home located in the Berkshire hills, remote setting minutes from Stockbridge ...
From $574 per night (USD)
VRBO
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VRBO
Modern Private Mountain Retreat - Close to Tanglewood & Lakes
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This amazing family home set on 5 acres in beautiful Tyringham, MA is an absolute escape from it all. Located just 20 mi ...
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VRBO
$Must See Jurassic Dino Suite At Jiminy Country Inn - Sleeps 4 Ski On\/Off at Mtn$
From $227 per night (USD)
Expedia
Must See Jurassic Dino Suite At Jiminy Country Inn - Sleeps 4 Ski On\/Off at Mtn
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to the Jurassic Era! This is the most epic suite in all of the Berkshires! Brand new, you will love a ...
From $227 per night (USD)
Expedia
From $695 per night (USD)
VRBO
Beautiful 4 Bedroom Townhouse in the Berkshires at Jiminy Peak Resort
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Located slope side at Jiminy Peak mountain resort in Hancock, MA, this townhouse offers guests 4 bedrooms, 3 bathrooms, ...
From $695 per night (USD)
VRBO
From $227 per night (USD)
Expedia
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: You want to pop out of bed, walk out your door, and be right on the mountain - this is the place for you. This ...
From $227 per night (USD)
Expedia
From $335 per night (USD)
VRBO
Berkshires Cabin 2 Mi to Appalachian Trail!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
An authentic Berkshire Mountains experience awaits in Otis at this 3-bedroom, 2-bathroom vacation rental by Lindal Cedar ...
From $335 per night (USD)
VRBO
From $709 per night (USD)
Expedia
Quintessential 6-BR Berkshires Lodge
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Summary: Retreat to the beauty of the Berkshires in this stunning, newly renovated lodge with a brand new pool! Features ...
From $709 per night (USD)
Expedia
From $219 per night (USD)
VRBO
Private apartment in beautiful country barn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Berkshire living at its best! This lovely shaker barn on 2 open acres has three apartments. All are private. Rent one o ...
From $219 per night (USD)
VRBO
$Ski-In\/Ski-Out at Jiminy Peak in the Country Inn$
From $255 per night (USD)
Expedia
Ski-In\/Ski-Out at Jiminy Peak in the Country Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Jiminy Peak Mountain Resort is the perfect Berkshire get away for skiing, mountain biking, snow shoeing, mountain coaste ...
From $255 per night (USD)
Expedia
From $406 per night (USD)
VRBO
Bentley Brook at Jiminy Peak ^^ 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski ...
From $406 per night (USD)
VRBO
From $331 per night (USD)
Expedia
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to Lake Ashmere! Our newly and completely renovated cottage features two bedrooms with comfy queen size beds, a ...
From $331 per night (USD)
Expedia
From $609 per night (USD)
VRBO
Lenox Grand Colonial with Pool by Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This 4 bedroom spacious home sits on a quiet cul-de-sac beneath October Mountain, with a picturesque back yard complete ...
From $609 per night (USD)
VRBO
$Rustic-Chic Home w\/ Decks: Pool + Lake Access$
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Expedia
Rustic-Chic Home w\/ Decks: Pool + Lake Access
Bedrooms:
3
Bathrooms:
6
Sleeps:
6
Natural beauty and upscale amenities pair perfectly together at this vacation rental! Nestled in the Otis Wood Lands com ...
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Expedia
From $337 per night (USD)
VRBO
Main Street Delight 1bedroom
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located on Main Street in downtown Lenox. A beautifully space fully equipped for all your needs. The eat-in kitchen has ...
From $337 per night (USD)
VRBO
From $309 per night (USD)
Expedia
Beachwood Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unique small cottage in the sought-after Beachwood community situated 2 miles from Tanglewood on Stockbridge Bowl. Featu ...
From $309 per night (USD)
Expedia

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