Holiday houses in New Ashford

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Top-rated holiday rentals in New Ashford

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Top Guest favourite
A red carriage house is set against a backdrop of mountains and blue skies. White Adirondack chairs circle a stone fire pit, while a picnic table and umbrella provide additional outdoor seating. Lush greenery surrounds the area, creating a serene environment.
Guesthouse in North Adams
5 out of 5 average rating, 312 reviews

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

Top Guest favourite
A charming yellow house features a welcoming front porch, adorned with potted flowers and comfortable seating. Generous windows allow natural light to brighten the space. The well-maintained landscaping includes trimmed hedges and a stone pathway leading to the inviting entrance.
Home in Williamstown
4.98 out of 5 average rating, 156 reviews

Quality, Comfort, Charm in Williamstown Center

Stay at this completely renovated house in the center of Williamstown! Conveniently located in a quiet neighborhood within easy walking distance to the town center, Williams College and The Clark Art Institute. The house was fully renovated in 2021. All new everything including appliances, a luxurious tile shower, fresh sheets and towels and lovely furnishings, all to make your stay comfortable and cozy. The living room has a beautiful gas fireplace and smart tv and in the summer, central air.

Guest favourite
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
4.95 out of 5 average rating, 210 reviews

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!

Top Guest favourite
A serene bedroom showcases a queen bed adorned with light bedding, set against calming green walls. A light-colored armoire and a small side table are visible, while natural light enters the room, creating a soft ambiance. A plush pillow is placed at the head of the bed.
Guest suite in Williamstown
4.96 out of 5 average rating, 254 reviews

Berkshire Guest Suite

Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

Guest favourite
An outdoor deck is presented with a large wooden table surrounded by chairs. Colorful cushions add comfort, and potted flowers brighten the space. Soft string lights hang above, illuminating a hammock and lounge chairs nearby, all set against a backdrop of lush greenery.
Guest suite in Hancock
4.82 out of 5 average rating, 202 reviews

Cozy apartment near Jiminy Peak

Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

Top Guest favourite
Apartment in North Adams
4.98 out of 5 average rating, 683 reviews

See MoCA from your mansion+Sauna! Near SKI

Near Ski & restaurants! 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!

Top Guest favourite
A two-story home is depicted, featuring a grey wooden exterior with multiple windows. A wooden deck with stairs leads to the entrance, surrounded by green grass and vibrant yellow flowers. The clear blue sky complements the inviting structure.
Farm stay in Pittsfield
4.99 out of 5 average rating, 291 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Guest favourite
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
4.9 out of 5 average rating, 143 reviews

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.

Top Guest favourite
A charming blue cottage with a wooden fence is showcased, featuring an American flag mounted on the front. The entrance includes a door framed by two windows, and a rustic fence leads to the path, surrounded by autumn leaves and forest greenery.
Cottage in Williamstown
4.9 out of 5 average rating, 202 reviews

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 pull out couch.. Dog friendly for up to 2 dogs at $100 per dog. My cottage sits on 13 privately owned acres. Partially fenced in 3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!

Top Guest favourite
A cozy kitchen area features a wooden dining table set with a small flower vase. Two white chairs are positioned around it, with a colorful rug underneath. Light wooden paneling and a window allow natural light to brighten the space, enhancing the welcoming ambiance.
Barn in Williamstown
4.96 out of 5 average rating, 330 reviews

Cozy barn apartment on the river

Private converted first floor barn apartment next to the Green River. Comfortable with unique furnishings and back door that opens to a riverfront covered patio. Sleeps 1-2 comfortably. Can accommodate 4 with the extra sleeper, tri-fold floor mattress, (Best for 1-2 smaller children). Private full bath. Great for 1-2 adults or a family with smaller children. It is on our property with a shared driveway.

Top Guest favourite
A comfortable living area features a sectional sofa and a single armchair arranged around a small metallic coffee table. A colorful area rug adds warmth to the space, while a lamp provides soft lighting. Exposed wooden beams enhance the architectural detail, and a door leads to the hallway.
Apartment in Williamstown
4.94 out of 5 average rating, 344 reviews

COLD SPRING

Welcome to your peaceful Berkshire retreat. Originally a barn, this charming two-bedroom, one-bath apartment features a fully equipped kitchen, skylight-vaulted ceilings, and original wood beams. Just a short drive from Mount Greylock, Jiminy Peak, and the Williamstown Theatre Festival—surrounded by scenic hikes and great local dining, it’s the perfect home base for your getaway.

Superhost
A rustic red barn stands among lush greenery, featuring large glass doors inviting natural light inside. The path leading to the barn is lined with gravel, and a stack of wood is neatly arranged beside the structure.
Home in Cheshire
4.86 out of 5 average rating, 224 reviews

19th c. Barn in The Berkshires

<b> Mason Hill Farm </b> is a celebration of everything we love about the Berkshires. Mountain views, a rushing swimmable brook, an historic restored barn and outbuildings surrounded by lush forest and grazing sheep. Follow us @ <b> mason_hill_farm </b> For weddings & events, please contact us for information on our sister property: Hinterland Hall!

Popular amenities for New Ashford holiday rentals