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House vacation rentals in Berkshire County

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Top-rated house rentals in Berkshire County

Guests agree: these houses are highly rated for location, cleanliness, and more.

Guest favorite
Home in Lee
Cozy Berkshires Cottage
Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)
May 22 – 29
$117 per night
Guest favorite
Home in Canaan
Country Cottage
Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.
Apr 24 – May 1
$135 per night
Guest favorite
Home in Dalton
Brooksong, the perfect Berkshires getaway
Part of this bright, sprawling, five-acre property was built in 1866 as a schoolhouse. Its historic charm now includes all the updated comforts of home, in an idyllic country setting that's lovely in all seasons. Located a short drive from Jiminy Peak, Brooksong is perfect for a ski vacation and close to plenty of lakes for summer fun. With a pool table, fire pit, and play set for kids, this is the perfect place to recharge and have fun with the people you care about. Welcome to Brooksong!
Oct 13 – 20
$311 per night

Popular amenities for Berkshire County house rentals

House rentals with a pool

Guest favorite
Home in Sheffield
Race Mountain House
May 2 – 9
$483 per night
Guest favorite
Home in West Stockbridge
Panoramic Views, Indoor Pool by Evergreen Home
Oct 4 – 11
$935 per night
Guest favorite
Home in Great Barrington
Newly Remodeled Private Estate-Pool, Tennis Court!
Feb 17 – 24
$925 per night
Guest favorite
Home in New Marlborough
Berkshires Colonial Farmhouse
Apr 5 – 12
$434 per night
Guest favorite
Home in Great Barrington
Stunning luxury home with fire pit
May 29 – Jun 5
$707 per night
Guest favorite
Home in Cheshire
Berkshire County modern home + pool
Jan 7 – 14
$379 per night
Guest favorite
Home in Pittsfield
Berkshire Getaway Ranch 3 acres + saltwater pool
Jun 14 – 21
$424 per night
Guest favorite
Home in Lanesborough
6-BR Country Estate 14-Min. to Jiminy Peak
Mar 24 – 31
$473 per night
Guest favorite
Home in Pittsfield
Stunning Berkshires Retreat, Large and Private
Jan 12 – 19
$613 per night
Guest favorite
Home in Canaan
Berkshire Lake House, gunite pool, Chef's Kitchen
Dec 5 – 12
$700 per night
Guest favorite
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
May 17 – 24
$700 per night
Guest favorite
Home in Egremont
Mountain View Estate Sleeps 18
Apr 1 – 8
$480 per night

Weekly house rentals

Guest favorite
Home in Chester
Riverfront Getaway
Dec 5 – 12
$159 per night
Guest favorite
Home in New Lebanon
The old sawmill from 1771
Dec 20 – 27
$125 per night
Guest favorite
Home in North Adams
The Lodge @ America’s Switzerland
Nov 15 – 22
$314 per night
Guest favorite
Home in Dalton
Cleveland House - renovated Berkshires' gem.
Feb 7 – 14
$380 per night
Guest favorite
Home in Great Barrington
Elegant Year-Round Lakeside Retreat with AC
Oct 12 – 19
$399 per night
Guest favorite
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
Jun 23 – 30
$225 per night
Superhost
Home in Becket
Real Estate:Therapy - Lake, Laundry, Love it
Jan 2 – 9
$238 per night
Guest favorite
Home in Cheshire
Ski at 19th c. Barn in The Berkshires
May 21 – 28
$338 per night
Guest favorite
Home in Becket
Lake front retreat - Stylish Berkshire home
Jun 25 – Jul 2
$528 per night
Guest favorite
Home in Egremont
A sunny, quiet chalet beautifully decorated.
Apr 4 – 11
$441 per night
Guest favorite
Home in Lenox
Heart of Lenox Walk to Town Cozy Cottage!
Jun 6 – 13
$223 per night
Guest favorite
Home in Pittsfield
Charming Gem in Heart of the Berkshires
Mar 2 – 9
$130 per night

Private house rentals

Guest favorite
Home in Lee
GreenHouse
Apr 15 – 22
$108 per night
Guest favorite
Home in Great Barrington
Granite Ledge, Modern home in a unique setting
Jun 6 – 13
$351 per night
Superhost
Home in Becket
Private Cabin On Over 12 Acres Of Woods!
Jun 20 – 27
$201 per night
Guest favorite
Home in Stockbridge
Bright Stockbridge country home, near everything!
Sep 21 – 28
$208 per night
Guest favorite
Home in Becket
Lindal Cedar Berkshires Lake House
Dec 13 – 20
$385 per night
Guest favorite
Home in Great Barrington
Waterfront Modern Lake Mansfield Retreat
Jun 11 – 18
$713 per night
Guest favorite
Home in West Stockbridge
Beautiful And Private Home Centrally Located
May 19 – 26
$671 per night
Guest favorite
Home in West Stockbridge
Berkshires-Enjoy The Peak, private home
Apr 3 – 10
$495 per night
Guest favorite
Home in Great Barrington
Sunsets On Blue Hill, Newly Renovated Farmhouse
Dec 19 – 26
$696 per night
Guest favorite
Home in Great Barrington
Newly remodeled home with all the modern amenities
Sep 12 – 19
$349 per night
Guest favorite
Home in Lanesborough
Berkshire Bliss- 6BR/Minutes from Jiminy +38 acres
Mar 21 – 28
$676 per night
Guest favorite
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
May 3 – 10
$320 per night

Destinations to explore