Vacation Rentals In The Berkshires
JustTheBerkshires.com
Lee, Lenox, Great Barrington, Stockbridge,
Williamstown, Becket, Otis, Pittsfield & More!
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Private Lake Cottage Near Jacob’s Pillow
And Tanglewood.
3 Bedrooms, 2 Baths, Sleeps 8
Becket, MA
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A Grand Estate In
Historic Stockbridge
6 Bedrooms, 8 Baths, Sleeps 12
9,000 Sq. Ft, 3 Acres, Downtown
Stockbridge, MA
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Perfectly Located In The
Center Of The Berkshires
4 Bedrooms, 4 Baths, Sleeps 12
10 Minutes From Lenox, Lee,
Stockbridge & Gt. Barrington
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The Lake House Guest
Cottages Of The Berkshires
Boutique-Style Cottages
On Pristine Pontoosuc Lake
Lanesboro, MA
(413) 446-0017
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Tanglewood, Downtown Lenox, Lee,
Stockbridge 5 Miles Or Less Away!
One Of A Kind Craftsmen Inspired Home.
5 Bedrooms, 3.5 Baths, Sleeps 15
Lee, MA
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Luxury Private Lakefront
In The Berkshires
5 Bedrooms, 2.5 Baths, Sleeps 8
Newly Renovated
Cheshire, MA
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Former 5 Bedroom B&B
5 Bedrooms, 5 Bath, Sleeps 10
Tanglewood Just 6.1 Miles Away
Pets Considered
Lee, MA
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Stockbridge Cottage Min.
From Downtown Lenox
3 BR, 1.5 BA, Sleeps 7, Less Than
5 Minutes To Tanglewood
No Pets
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Huge Luxe Williamstown
Updated Victorian
5 BR, 5.5 BA, Sleeps 10
Walk To Spring Street
Pets Considered
Williamstown, MA
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Vacation rentals in the Berkshires make for a memorable Berkshire vacation. Stay at one of the many vacation home rentals throughout the Berkshires. From vacation homes for rent to vacation apartment and condo rentals, each vacation rental offers a truly unique lodging experience. View our map to find vacation home rentals in the Northern Berkshires, Central Berkshires and Southern Berkshires. Many vacation rentals are located within a short distance to one of our wonderful Berkshire attractions such as Tanglewood, MASS MoCA, The Colonial Theatre, Norman Rockwell Museum, Barrington Stage Company, Williamstown Theatre Festival, Clark Art, Ski Areas, Colleges and more.
Northern Berkshires
Central Berkshires
Southern Berkshires
Adams, MA
Cozy Family Friendly Home In The Heart Of The Berkshires
2 Bedrooms, 1.5 Baths, Sleeps 6
Adams, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Berkshires Gem – Walk To Town And Trails!
4 Bedrooms, 2 Baths, Sleeps 8
Adams, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Alford, MA
NEW: Gorgeous, Unique, Craftsman Cottage
2 Bedrooms, 2 Baths, Sleeps 4
Alford, MA
Southern Berkshires
Vacation Home Rental Rates & Information
Beautiful Berkshire Farm House On 160+ Acres
7 Bedrooms, 4.5 Baths, Sleeps 16
Alford, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Berkshire Chalet Getaway!
3 Bedrooms, 2 Baths, Sleeps 6
Alford, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Becket, MA
A-Frame in Sherwood Forest
1 Bedrooms, 1 Bath, Sleeps 5
Becket, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Peace And Quiet At Sea
2 Bedrooms, 2 Bath, Sleeps 6
Becket, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Lakefront Cottage In The Berkshires
2 Bedrooms, 1 Bath, Sleeps 4
Becket, MA
Central Berkshires
Vacation Home Rental Rates & Information
Charlemont, MA
Hidden Gem At Base Of Ski Mountain
2 Bedrooms, 1 Bath, Sleeps 6
Charlemont, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
StrautmanHaus – All-Season Chalet At Berkshire East
4 Bedrooms, 2 Bath, Sleeps 10
Charlemont, MA
Northern Berkshires
Vacation Home Rental Rates & Information
Charming 2022 Renovated 1867 Farmhouse
4 Bedrooms, 2 Bath, Sleeps 8
Charlemont, MA
NorthernBerkshires
Vacation Home Rental Rates & Information
Cheshire, MA
Ski At 19th C. Renovated Barn In The Berkshires
3 Bedrooms, 2 Bath, Sleeps 10
Cheshire, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Luxury Private Lakefront In The Berkshires
4 Bedrooms, 2.5 Bath, Sleeps 8
Cheshire, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Egremont, MA
TreeHouse: Berkshires Chalet In Sun-Dappled Forest
3 Bedrooms, 3 Bath, Sleeps 6
Egremont, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Charming Cottage w/ Sauna
2 Bedrooms, 1.5 Bath, Sleeps 4
Egremont, MA
Southern Berkshires
Vacation Home Rental Rates & Information
Private Berkshires Retreat
4 Bedrooms, 2.5 Bath, Sleeps 8
Egremont, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Great Barrington, MA
Just You, Perfect Cozy Winter Getaway
3 Bedrooms, 2.5 Bath, Sleeps 6
Great Barrington, MA
Southern Berkshires
Vacation Home Rental Rates & Information
14 Min To Butternut, Great Barrington Guest Cottage
3 Bedrooms, 1.5 Bath, Sleeps 5
Great Barrington, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Beautiful, Newly-Renovated House On ‘The Hill’
4 Bedrooms, 3 Bath, Sleeps 8
Great Barrington, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
New Remodeled 3BR Country Castle
3 Bedrooms, 3 Bath, Sleeps 8
Great Barrington, MA
Southern Berkshires
Vacation Home Rental Rates & Information
Cozy Log Home *The Berkshires*
2 Bedrooms, 1 Bath, Sleeps 8
Great Barrington, MA
Southern Berkshires
Vacation Home Rental Rates & Information
Lakefront Berkshires Retreat w/Deck, Dock & Boat!
4 Bedrooms, 2 Bath, Sleeps 10
Great Barrington, MA
Southern Berkshires
Vacation Home Rental Rates & Information
Modern Victorian, Walk To Town
4 Bedrooms, 3 Bath, Sleeps 8
Great Barrington, MA
Southern Berkshires
Vacation Home Rental Rates & Information
Chic Updated Downtown Great Barrington
3 Bedrooms, 2.5 Bath, Sleeps 14
Great Barrington, MA
Southern Berkshires
Vacation Home Rental Rates & Information
Romantic Berkshires Cottage – Stunning Views, Pool
1 Bedrooms, 1 Bath, Sleeps 3
Great Barrington, MA
Southern Berkshires
Vacation Home Rental Rates & Information
Hancock, MA
Mountain View Suite
1 Bedrooms, 1 Bath, Sleeps 4
Hancock, MA
Northern Berkshires
Vacation Home Rental Rates & Information
Hancock Log Cabin Retreat
3 Bedrooms, 2 Bath, Sleeps 6
Hancock, MA
Northern Berkshires
Vacation Home Rental Rates & Information
Quiet & Private, Small Horse Farm
1 Bedrooms, 1 Bath, Sleeps 4
Hancock, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Hawley, MA
HawleyHaus – Log Cabin In The Berkshires!
3 Bedrooms, 2 Bath, Sleeps 10
Northern, MA
Central Berkshires
Vacation Home Rental Rates & Information
Country Home w/Babbling Brook
3 Bedrooms, 1.5 Bath, Sleeps 8
Hawley, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Stunning Mountain Top Lodge
7 Bedrooms, 3.5 Bath, Sleeps 10
Hawley, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Hinsdale, MA
Gorgeous Lake Ashmere Home
3 Bedrooms, 3 Bath, Sleeps 6
Hinsdale, MA
Central Berkshires
Vacation Home Rental Rates & Information
Quiet Lake House w/Beautiful Water Views
2 Bedrooms, 2 Bath, Sleeps 8
Hinsdale, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Private Lake Front Beach In The Berkshires
3 Bedrooms, 4 Bath, Sleeps 8
Hinsdale, MA
Central Berkshires
Vacation Home Rental Rates & Information
Lanesborough, MA
Berkshire Village Carriage House
1 Bedrooms, 1 Bath, Sleeps 2
Lanesborough, MA
Central Berkshires
Vacation Home Rental Rates & Information
NEW! Stylish Berkshire Haven Minutes To Jiminy Peak
3 Bedrooms, 1.5 Bath, Sleeps 6
Lanesborough, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
NEW! Spacious Mtn Home, 5 Miles To Jiminy Peak!
3 Bedrooms, 2 Bath, Sleeps 6
Lanesborough, MA
Central Berkshires
Vacation Home Rental Rates & Information
A Beautiful Log Cabin In The Woods
2 Bedrooms, 1 Bath, Sleeps 5
Lanesborough, MA
Central Berkshires
Vacation Home Rental Rates & Information
Berkshire Pontoosuc Lake Beauty
5 Bedrooms, 3.5 Bath, Sleeps 14
Lanesborough, MA
Central Berkshires
Vacation Home Rental Rates & Information
Wildlife Cottage By The Lake
3 Bedrooms, 1.5 Bath, Sleeps 6
Lanesborough, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Berkshire Lake House Vacation Rental
4 Bedrooms, 2 Bath, Sleeps 6
Lanesborough, MA
Central Berkshires
Vacation Home Rental Rates & Information
6BR Berkshire Bliss, 38 Acres Of Nature
6 Bedrooms, 4.5 Bath, Sleeps 14
Lanesborough, MA
Central Berkshires
Vacation Home Rental Rates & Information
Lee, MA
Gorgeous, Private, Family-Friendly, Organic Home
3 Bedrooms, 2 Bath, Sleeps 6
Lee, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Spacious Berkshire Home – Year Round Retreat
5 Bedrooms, 2.5 Bath, Sleeps 12
Lee, MA
Southern Berkshires
Vacation Home Rental Rates & Information
The Playhouse: 7,000 Sq. Ft. Of Berkshires
6 Bedrooms, 5 Bath, Sleeps 20
Lee, MA
Southern Berkshires
Vacation Home Rental Rates & Information
Lenox, MA
Heart Of Lenox, Walk To Town, Cozy Cottage!
2 Bedrooms, 1 Bath, Sleeps 4
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information
Vacation Or Work Away From Home!
2 Bedrooms, 1.5 Bath, Sleeps 5
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information
5 Star Casual Elegance For 5 Star Guests
3 Bedrooms, 2.5 Bath, Sleeps 6
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information
Large Lenox Home w/Pool; Ideal Berkshire Location!
4 Bedrooms, 2.5 Bath, Sleeps 8
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information
Beautiful Lenox Home, 3 Mi To Shakespeare & Co!
3 Bedrooms, 2 Bath, Sleeps 6
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information
Private Guest House In Dtwn Lenox, Walk To Dining!
3 Bedrooms, 2.5 Bath, Sleeps 6
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information
Private Access To Laurel Lake – Winter Sports Fun!
4 Bedrooms, 2 Bath, Sleeps 10
Lenox, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Lovely Home In Heart Of Lenox
2 Bedrooms, 2 Bath, Sleeps 4
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information
Middlefield, MA
Sunny, Stylish Berkshire Mountain Retreat
4 Bedrooms, 2 Bath, Sleeps 8
Middlefield, MA
Central Berkshires
Vacation Home Rental Rates & Information
Monterey, MA
Cozy Monterey Family Chalet
2 Bedrooms, 1 Bath, Sleeps 6
Monterey, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Country Cottage For 2 On Private Setting
1 Bedrooms, 1 Bath, Sleeps 2
Southern, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Stunning Lakefront Berkshire Rental, Lake Garfield
5 Bedrooms, 2 Bath, Sleeps 8
Southern, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
New Marlborough, MA
Private Rustic Cottage w/Lake Access
2 Bedrooms, 1 Bath, Sleeps 6
New Marlborough, MA
Southern Berkshires
Vacation Home Rental Rates & Information
The Mill River Cabin w/ Fireplace & River View!
2 Bedrooms, 1 Bath, Sleeps 5
New Marlborough, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Perfect Vacation Get Away
1 Bedrooms, 1 Bath, Sleeps 4
New Marlborough, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
North Adams, MA
Lovley, Romantic, Fun, En Suite
1 Bedrooms, 1 Bath, Sleeps 4
North Adams, MA
Northern Berkshires
Vacation Home Rental Rates & Information
Beautiful Berkshire Lakeside Home
3 Bedrooms, 1.5 Bath, Sleeps 8
North Adams, MA
Northern Berkshires
Vacation Home Rental Rates & Information
Art House! Spacious Getaway By Mass Moca
6 Bedrooms, 2 Bath, Sleeps 10
North Adams, MA
Northern Berkshires
Vacation Home Rental Rates & Information
Otis, MA
The Meadows House
1 Bedrooms, 1 Bath, Sleeps 7
Otis, MA
Southern Berkshires
Vacation Home Rental Rates & Information
4BR/3BA Lakefront/Ski House In Berkshires
4 Bedrooms, 3 Bath, Sleeps 10
Otis, MA
Southern Berkshires
Vacation Home Rental Rates & Information
NEW! Berkshires Cabin 2 Mi To Appalachian Trail!
3 Bedrooms, 2 Bath, Sleeps 7
Otis, MA
Southern Berkshires
Vacation Home Rental Rates & Information
Pittsfield, MA
Lovely Family Retreat In The ♥️ Of The Berkshires!
4 Bedrooms, 2 Bath, Sleeps 7
Pittsfield, MA
Central Berkshires
Vacation Home Rental Rates & Information
Charming Historic Home
5 Bedrooms, 3.5 Bath, Sleeps 10
Pittsfield, MA
Central Berkshires
Vacation Home Rental Rates & Information
Dancing Horse Lodge
3 Bedrooms, 1 Bath, Sleeps 6
Pittsfield, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Chic Pittsfield Home With A View!
3 Bedrooms, 1.5 Bath, Sleeps 6
Pittsfield, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Honeysuckle Rose Cottage
2 Bedrooms, 1 Bath, Sleeps 4
Pittsfield, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Peru, MA
Swiss Chalet Style Timber Frame Home
3 Bedrooms, 2 Bath, Sleeps 6
Peru, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Remote & Relaxing Cabin In The Berkshires
3 Bedrooms, 2 Bath, Sleeps 8
Peru, MA
Central Berkshires
Vacation Home Rental Rates & Information
The Perfect Escape
3 Bedrooms, 2 Bath, Sleeps 8
Peru, MA
Central Berkshires
Vacation Home Rental Rates & Information
Richmond, MA
Spacious Berkshire Summer Rental
3 Bedrooms, 3 Bath, Sleeps 7
Richmond, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Private Apartment In Beautiful Country Barn
1 Bedrooms, 1 Bath, Sleeps 4
Richmond, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Relaxing Getaway In The Beautiful Berkshires
4 Bedrooms, 2.5 Bath, Sleeps 12
Richmond, MA
Central Berkshires
Vacation Home Rental Rates & Information
Sandisfield, MA
Sweet Dreams Retreat
1 Bedrooms, 1 Bath, Sleeps 3
Sandisfield, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Cabin With 3 Acres
4 Bedrooms, 3 Bath, Sleeps 10
Sandisfield, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Iconic Cabin In The Berkshires
6 Bedrooms, 3.5 Bath, Sleeps 12
Sandisfield, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Savoy, MA
Retreat In The Woods
2 Bedrooms, 1 Bath, Sleeps 4
Savoy, MA
Northern Berkshires
Vacation Home Rental Rates & Information
Sheffield, MA
Elterwater–Your lakefront Oasis
2 Bedrooms, 2 Bath, Sleeps 4
Sheffield, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Cheerful 3BR Cottage With Woodstove
3 Bedrooms, 2.5 Bath, Sleeps 8
Sheffield, MA
Southern Berkshires
Vacation Home Rental Rates & Information
NEW! Waterfront Sheffield Escape
3 Bedrooms, 2 Bath, Sleeps 6
Sheffield, MA
Southern Berkshires
Vacation Home Rental Rates & Information
South Lee, MA
Upscale Architecturally Designed Berkshire Home
4 Bedrooms, 3 Bath, Sleeps 8
South Lee, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Architect Designed Home
4 Bedrooms, 3 Bath, Sleeps 8
South Lee, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Stockbridge, MA
Location!!! Location!!! Berkshire Glamour
4 Bedrooms, 3 Bath, Sleeps 8
Stockbridge, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Stockbridge Cape Near Tanglewood
4 Bedrooms, 2 Bath, Sleeps 7
Stockbridge, MA
Southern Berkshires
Vacation Home Rental Rates & Information
Spectacular Housatonic River View
2 Bedrooms, 2 Bath, Sleeps 4
Stockbridge, MA
Southern Berkshires
Vacation Home Rental Rates & Information
Washington, MA
Berkshires Log Cabin, Peace & Tranquility Awaits
3 Bedrooms, 1 Bath, Sleeps 8
Washington, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Beautiful Timber Frame Home
2 Bedrooms, 1 Bath, Sleeps 6
Washington, MA
Southern Berkshires
Vacation Home Rental Rates & Information
Shingle Style, Timber Frame, Berkshire Cottage
3 Bedrooms, 2 Bath, Sleeps 8
Washington, MA
Southern Berkshires
Vacation Home Rental Rates & Information
West Stockbridge, MA
Charming Unique Cottage Relax & Enjoy
2 Bedrooms, 1 Bath, Sleeps 5
West Stockbridge, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Gorgeous Home, Nature Lover’s Delight
4 Bedrooms, 4 Bath, Sleeps 8
West Stockbridge, MA
Southern Berkshires
Vacation Home Rental Rates & Information
Sweet Escape w/Indoor Pool
4 Bedrooms, 4 Bath, Sleeps 7
West Stockbridge, MA
Southern Berkshires
Vacation Home Rental Rates & Information
Williamstown, MA
Charming Downtown Williamstown Cottage
3 Bedrooms, 2 Bath, Sleeps 7
Williamstown, MA
Northern Berkshires
Vacation Home Rental Rates & Information
North Getaway Cottage
4 Bedrooms, 2 Bath, Sleeps 7
Williamstown, MA
Northern Berkshires
Vacation Home Rental Rates & Information
Cozy & Quaint Country Cottage
2 Bedrooms, 1 Bath, Sleeps 4
Williamstown, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Huge Luxe Williamstown Updated Victorian
5 Bedrooms, 5.5 Bath, Sleeps 10
Williamstown, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information