Vacation rentals in Cheshire

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Top-rated vacation rentals in Cheshire

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

Guest favorite
Cabin in Savoy
The Camp - 20 Minutes to Berkshire East!
Enjoy the peaceful silence, private forested expanses, wildlife, and unforgettable starry night skies from this wonderful home. Only 8 minutes to the village of Charlemont and 5 to the Tannery Falls entrance of the Savoy State Forest. During your escape on the mountain rest assured that you’re only a 30 minute drive to Norths Adams, Greenfield. Highlight your visit with journeys to Berkshire East Ski Resort, Thunder Mountain Biking, Zoar Outdoor River Rafting, MASS MoCA, or the Clark Art Museum.
Jun 15 – 22
$99 per night
4.98 out of 5 average rating, 184 reviews
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!
Apr 18 – 25
$273 per night
4.92 out of 5 average rating, 168 reviews
Guest favorite
Home in Dalton
The Yellow House
The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. This historic small town offers many activities including Jacob's Pillow, hiking trails, skiing, Mass MoCA, and The Clark Art Institute. It is close to Tanglewood in Lenox and the Norman Rockwell Museum in Stockbridge. Located steps away from The Stationery Factory, which houses a food market, gallery spaces, artisan shops, coffee shop, and the Shire Brewhouse & pub.
Oct 7 – 14
$104 per night
4.91 out of 5 average rating, 111 reviews

Popular amenities for Cheshire vacation rentals

Stay near Cheshire's top sights

Whitney's Farm Market & Garden Center20 locals recommend
Berkshire Outfitters4 locals recommend
Lakeview Orchard8 locals recommend

Other great vacation rentals in Cheshire

Guest favorite
Farm stay in New Ashford
Sheep Barn on the Greylock Valley Estate
May 3 – 10
$162 per night
4.89 out of 5 average rating, 217 reviews
Guest favorite
Cottage in Lanesborough
Stone School Cottage
Mar 30 – Apr 6
$147 per night
4.93 out of 5 average rating, 219 reviews
Guest favorite
Home in Dalton
Cleveland House - renovated Berkshires' gem.
Apr 18 – 25
$380 per night
4.99 out of 5 average rating, 118 reviews
Guest favorite
Apartment in Petersburg
The Beer Diviner Brewery Apartment
Jul 29 – Aug 5
$59 per night
4.85 out of 5 average rating, 140 reviews
Guest favorite
Home in Cheshire
Large Secluded Berkshire Home
Jul 27 – Aug 3
$338 per night
4.8 out of 5 average rating, 144 reviews
Guest favorite
Guesthouse in Stephentown
Dog Friendly Studio
Sep 4 – 11
$167 per night
5.0 out of 5 average rating, 352 reviews
Guest favorite
Apartment in Plainfield
Sunny, light filled loft in 1873 Colonial
Aug 6 – 13
$104 per night
4.97 out of 5 average rating, 236 reviews
Guest favorite
Cottage in Williamstown
Cute Cozy Comfy Cottage in the Berkshires
Jan 15 – 22
$141 per night
4.9 out of 5 average rating, 164 reviews
Guest favorite
Home in Cheshire
The Berkshires Hummingbird House
Apr 26 – May 3
$167 per night
5.0 out of 5 average rating, 19 reviews
Guest favorite
Home in Cheshire
Berkshires Lakefront Retreat by Evergreen Home
Dec 20 – 27
$584 per night
4.92 out of 5 average rating, 24 reviews
Guest favorite
Home in Adams
Mountain View Hideaway
Apr 7 – 14
$93 per night
4.9 out of 5 average rating, 61 reviews
Guest favorite
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
Mar 26 – Apr 2
$320 per night
5.0 out of 5 average rating, 88 reviews

Destinations to explore