Vacation rentals in Cheshire

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Top-rated vacation rentals in Cheshire

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Guest favorite

A charming stone building is surrounded by lush greenery and colorful flowers, including pink and white blossoms. The sign, featuring 'Stone School Cottage,' is prominently displayed. Large windows indicate a bright interior. The setting offers a peaceful and inviting entrance to the accommodation.

Cottage in Lanesborough

Stone School Cottage

Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.

4.93 out of 5 average rating, 264 reviews

Top guest favorite

An open living space features high wooden ceilings with exposed beams and a stylish pool table positioned at the center. A cozy couch sits nearby, with a staircase leading to a loft area visible in the background. Natural light fills the room through large windows.

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!

4.93 out of 5 average rating, 211 reviews

Top guest favorite

A bright living area features a yellow couch and two accent chairs, inviting relaxation. A patterned area rug centers the space, while natural light filters through large windows. A staircase is visible in the background, along with decorative plants and artwork adorning the walls.

Home in Pittsfield

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

4.95 out of 5 average rating, 232 reviews

Guest favorite

A serene lake reflects a clear blue sky and lush green forests surrounding it. The water, calm and inviting, showcases the vibrant colors of autumn foliage along the banks, with tall grasses in the foreground adding to the natural landscape.

Cottage in Lanesborough

Wildlife Lakeside Cottage; views/wildlife

Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. There is an incredible amount of wildlife, especially all types of birds. Sunny views abound. The house boasts a bright wood interior with a cozy feel. It has two and a half baths. There is a first floor queen bedroom with cathedral ceiling, and on the 2nd floor another queen room and a twin room-2 single beds.The adjacent lake teams with wildlife, seasonal weeds do grow. Contact us for conditions.

4.85 out of 5 average rating, 300 reviews

Guest favorite

The exterior of a renovated antique farmhouse is displayed, featuring a white facade and multiple entrances framed by greenery. A spacious lawn surrounds the house, complemented by mature trees in the background under a clear blue sky.

Home in Lanesborough

Elmwood Farmhouse

Renovated farmhouse in the Berkshires, Perfect for family gatherings, or weekends away. The house is spacious and welcoming with a sunny deck and welcoming porch. Dog friendly with a fully enclosed yard. Close to all the Berkshires has to offer from Tanglewood, to Mass MOCA, and other cultural and natural attractions.. Near Mount Greylock, and other outdoor destinations. The Ashuwilticook Bike Trail is across the street. Whitney's Farm stand nearby with fresh Produce and Deli .

4.9 out of 5 average rating, 124 reviews

Guest favorite

Cabin in Windsor

Stone cabin in the Berkshires

Twin Brooks is a magical retreat in the woods of the Northern Berkshires. 30-40 minutes drive Mass Moca, the Clark, Tanglewood, Berkshires East, and Jiminy Peak. Less than 10 minutes away from spectacular Nordic skiing and walking trails at the Notch. Close to countless other hiking trails and scenic lakes for swimming and kayaking. Relax with the sound of the bubbling brook in the distance and enjoy an evening at the fire pit. Scenic Fall season gives way to a winter wonderland.

4.88 out of 5 average rating, 32 reviews

Guest favorite

A quaint cottage is nestled among trees, featuring a welcoming front porch with several potted plants and outdoor seating. The light-colored exterior is complemented by blue accents on the chairs, while the wooden deck extends invitingly, creating a serene outdoor space.

Cabin in Cheshire

Private Paradise in the Berkshires

Your own private and romantic getaway behind a small orchard. A sweet running brook and outdoor shower! A short drive to all Berkshire cultural events -- Tanglewood, Jacob's Pillow, theatre festivals and more. Great dining nearby. Perfect for 2! Under COVID-19 regulations in Massachusetts, I am required to allow at least 24 hours between guests. It's a drag, but it is intended to keep us all healthy! Please forgive any inconveniences this might create in your trip plans.

4.89 out of 5 average rating, 176 reviews

Top guest favorite

Adirondack chairs are arranged along a grassy area by the lake, offering scenic views of the water and surrounding greenery. A gently sloping bank leads to the water's edge, where stairs provide access to the dock. Lush hills rise in the background.

Home in Cheshire

Berkshires Lakefront Retreat by Evergreen Home

Evergreen Home Vacation Rentals invites you to this serene retreat on 4 private acres, just 15 minutes from Jiminy Peak. This newly renovated 4BR/2.5BA home offers breathtaking views of both the lake and mountains. Discover a chef’s dream kitchen with top-tier appliances, perfect for culinary creativity. After a day of adventure, unwind in the luxurious soaking tub or relax by the fire. Whether seeking peace or mountain thrills, this is your perfect Berkshire escape.

4.97 out of 5 average rating, 59 reviews

Guest favorite

Home in Cheshire

Cheshire Cove | Waterfront • Kayak • Firepit

Escape to this charming lakeside oasis on Cheshire Lake in the heart of The Berkshires. This nicely appointed 2-bedroom, 1-bath home offers stunning water views, a warm indoor fireplace, and a spacious deck perfect for relaxing or dining outdoors. Enjoy kayaking right from the backyard, grilling al fresco, or cooking up some s'mores at the fire pit. Whether you seek tranquility or adventure, this spot is your perfect lakeside escape, book now before it's too late!

4.87 out of 5 average rating, 31 reviews

Top guest favorite

A charming Victorian home is showcased at dusk, with bright windows illuminating the exterior. The wraparound porch features decorative railings and flower planters, complementing the elegant architectural details. The two-story structure is framed by a darkening sky, enhancing its inviting presence in the neighborhood.

Home in Adams

Beautiful Victorian. The heart of the Berkshires.

The whole group will enjoy easy access to everything from this centrally located place. The house has been completely renovated. The side patio has plenty of room for a large group with a brand new Weber grill and propane fire pit. Enjoy morning coffee on the front porch. Just steps from the Ashuwillicook Rail Trail. Greylock Glen is less than a half mile away with hiking trails. Mass MoCA is 5 miles away. This Victorian beauty is cozy, warm, and inviting.

4.91 out of 5 average rating, 149 reviews

Top guest favorite

Home in North Adams

Steps to MoCA private house + SAUNA!

Welcome to the Gardener’s Cottage at Chase Hill—the historic estate of the owners of the factory that became MASS MoCA. More than just houses, Chase Hill is an experience: gardens, fire pits, sauna, massages, occasional music rehearsals. Just a 5-minute walk to MASS MoCA, 10 mins by car to Williams & Clark. ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!

4.98 out of 5 average rating, 555 reviews

Guest favorite

A spacious living area features a warm wood-paneled ceiling and modern furnishings. Two sleek sofas are arranged around a wooden coffee table, while armchairs provide additional seating. Natural light floods the space through large windows framed by light curtains, enhancing the welcoming atmosphere.

Home in Cheshire

Large Secluded Berkshire Home

Rustic Berkshire Retreat Relax in this cozy home on 3.5 private acres in Cheshire with scenic mountain views. Just 5 minutes to downtown Adams and the Susan B. Anthony Birthplace, and under 25 minutes to MASS MoCA, Williams College, Mt. Greylock, and Pittsfield. Tanglewood and Jiminy Peak are within 45 minutes. Note: Sand Mill Road bridge construction in August 2024 may add about 5 minutes to travel times.

4.81 out of 5 average rating, 165 reviews