Vacation rentals in Cheshire

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Cheshire

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

1 of 1 pages1 / 1

Top guest favorite

Home in Adams

Relaxing Berkshires Home With a View!

New Charming Berkshire Retreat with Mountain Views! Welcome to your perfect getaway in the heart of the Berkshires! This spacious home offers, 3 bedrooms, 1.5 baths with a spacious yard which offers a serene escape with stunning views of Mount Greylock, making it an ideal spot for families, friends, or anyone looking to unwind in nature with hiking trails and ski resorts nearby. Walking distance to downtown and Ashuwillticook Rail Trail. MASS MoCA- 13 minutes Skiing- 26 minutes Hiking-5 minutes

LocationFamilyAmenities

5.0 out of 5 average rating, 17 reviews

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.

ValueFamilyLayout

4.93 out of 5 average rating, 266 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!

FamilyLocationQuiet

4.93 out of 5 average rating, 214 reviews

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!

LocationValueLayout

4.95 out of 5 average rating, 242 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.

LocationValueAccess

4.85 out of 5 average rating, 301 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 .

LocationFamilyOutdoor spaces

4.9 out of 5 average rating, 125 reviews

Guest favorite

A serene view of a spacious home nestled among lush greenery and trees. A tranquil pond reflects the house and surrounding foliage. Autumn colors are visible in the trees, adding warmth to the landscape.

Home in Dalton

Willowbrook: A Sun Filled, Mid-century Modern Home

Welcome to Willowbrook! Our home is the perfect getaway from which to explore all that the Berkshires has to offer. This secluded yet close to town property has access to miles of hiking trails, ski resorts, and cultural institutions. Once home to members of the Crane family who have lived in Dalton since 1799, you can stay in a piece of history and even visit the Crane paper museum in town! We are so looking forward to hosting you in this beautiful place we call home.

FamilyLocationSleep quality

4.78 out of 5 average rating, 114 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.

LocationFamilyHospitality

4.97 out of 5 average rating, 60 reviews

Top guest favorite

Apartment in North Adams

See MoCA from your mansion+Sauna!

Large bi-level 4 bedroom apartment tucked away on a hilltop oasis above Mass MoCA (3 mins by foot). 10 mins drive to Williams College & Clark. Whimsically restored (fast Wi-Fi & great water pressure). Fully private with no shared spaces + outdoor Sauna! Your stay’s proceeds allow us to host refugee/immigrant musicians pro bono year-round at @chasehillartistretreat Note: more dates are often available beyond what the calendar shows. Please don’t hesitate to inquire!

FamilyLocationLaundry

4.97 out of 5 average rating, 742 reviews

Guest favorite

Home in Cheshire

Berkshire's Family Gathering & Mountain Escape!

Newly Renovated Berkshires home on 10 acres of private land. Immerse yourself in nature and explore the property in all seasons. Accommodating 10-12 comfortably, with 4BR, 3 full bath, wood fireplace, BBQ Grill, Fire pit seating 8, 2 kayaks and a canoe. Indoor garage parking for 2 cars with exterior parking for another 3 vehicles. Escape to the lower level game room with a Pool Table, Ping Pong, Foose Ball, Hot Shot, Dart Board and an additional living room area.

LocationFamilyDecor

4.93 out of 5 average rating, 15 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.

FamilyValueWalkability

4.91 out of 5 average rating, 150 reviews

Top guest favorite

A charming red farmhouse is framed by lush greenery, showcasing a two-story structure with multiple gabled roofs and large windows. A gravel pathway leads up to the front porch, which features seating, while a garage is visible to one side.

Farm stay in Dalton

Gorgeous Working Farm in the Berkshires

Get away from it all when you stay on our beautiful 4th generation working farm. Farmhouse backs up to 1000 acres of woodlands with trails, brooks and small bodies of water. See farm animals out grazing in the fields while you get cozy in our 5 bedroom farmhouse. Toast marshmallows over a campfire, walk the many roads and trails, or just sip some wine on the porch and enjoy the clean air and delightful views. Night skies are breathtaking on a clear evening.

FamilyLocationNearby

5.0 out of 5 average rating, 20 reviews