Vacation rentals in Berkshire County
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Top-rated vacation rentals in Berkshire County
Guests agree: these stays are highly rated for location, cleanliness, and more.
Home in Lee
4.89 out of 5 average rating, 234 reviewsCozy 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 8 – 15
Loft in Great Barrington
4.99 out of 5 average rating, 296 reviewsThe Old Red Barn
Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.
Apr 5 – 12
Home in Canaan
5.0 out of 5 average rating, 131 reviewsCountry 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.
Mar 12 – 19
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Other great vacation rentals in Berkshire County
Apartment in Sheffield
5.0 out of 5 average rating, 318 reviewsHideaway with Spectacular Berkshire Views
Jun 18 – 25
Guesthouse in Stephentown
5.0 out of 5 average rating, 355 reviewsDog Friendly Studio
Nov 12 – 19
Cottage in Great Barrington
4.93 out of 5 average rating, 234 reviewsArtist Cottage
Dec 14 – 21
Guest suite in Williamstown
4.96 out of 5 average rating, 202 reviewsBerkshire Guest Suite
Jun 16 – 23
Apartment in Sheffield
4.92 out of 5 average rating, 120 reviewsPrivate Berkshire Barn Apartment
Oct 20 – 27
Home in Monterey
4.92 out of 5 average rating, 306 reviewsCharming cottage w/ gorgeous views.
Feb 26 – Mar 5
Home in Lee
5.0 out of 5 average rating, 224 reviewsBerkshire Mountain retreat with Urban eco-luxuries
Mar 19 – 26
Guest suite in Hancock
4.83 out of 5 average rating, 151 reviewsCozy apartment near Jiminy Peak
Nov 26 – Dec 3
Cottage in Becket
4.95 out of 5 average rating, 122 reviewsCozy lakeside cottage
Nov 30 – Dec 7
Cottage in Becket
4.94 out of 5 average rating, 237 reviewsBERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.
Oct 17 – 24
Guest suite in Austerlitz
4.86 out of 5 average rating, 137 reviewsRustic-Modern Studio - Near Hudson, Chatham, & GB
Feb 26 – Mar 5
Cabin in North Adams
4.95 out of 5 average rating, 182 reviewsMahican Cabin - A Private Nature's Reserve For 2
Sep 11 – 18
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