Vacation rentals in Taconic Mountains

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Top-rated vacation rentals in Taconic Mountains

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Top guest favorite
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, 155 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.

Top guest favorite
Apartment in North Adams
4.96 out of 5 average rating, 657 reviews

Steps to MoCA Near SKI: 2bd + SAUNA!

Near ⛷️ SKI resorts: Jiminy Peak, Berkshire East Mountain and others. A large, private 2-bedroom apt at the Small Mansion of Chase Hill Estate. Outdoor Sauna! Just a 5 minute-walk to MASS MoCA & downtown restaurants, 10 mins drive to Williams College & Clark. Whimsically restored (fast Wi-Fi & great water pressure!) and part of @chasehillartistretreat ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 349 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favorite
Cabin in Shaftsbury
4.99 out of 5 average rating, 307 reviews

The Hygge Loft- mid-mod cabin on 70 forested acres

The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

Top guest favorite
A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.
Home in Bennington
5 out of 5 average rating, 103 reviews

Vermont Farmhouse •Walk to Village & Hiking Trails

Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

Top guest favorite
A wooden structure with a deck extends into the greenery, framed by tall hop poles. The building features a large front porch, inviting outdoor seating, and an entrance accentuated by surrounding trees and a grassy area leading up to it.
Apartment in Petersburgh
4.89 out of 5 average rating, 209 reviews

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

Guest favorite
A cozy bedroom features a brass bed adorned with a textured blanket and decorative pillows. The walls are finished in warm wood paneling, complemented by two bedside lamps. A kitchenette is visible in the background, enhancing the cabin's charm.
Cabin in Pownal
4.97 out of 5 average rating, 259 reviews

Historic Cozy Cabin Six

Soak up this fully renovated and modernized cabin from the 1920s. We kept and reused many vintage materials and fixtures while expanding its footprint with a new bathroom. This charming cabin has also been re-sited so that it is now in proximity to the former Inn at Oak Hill B&B which affords it shared use of amenities like parking, laundry, and privacy. Many antiques decorate the interior including a beautiful brass bed not to forget the coziest kitchenette in the world!

Top guest favorite
The kitchen features modern appliances, including a stainless steel refrigerator and a sleek oven range. An orange barn-style door adds a pop of color, contrasting with the navy cabinetry. Cooking utensils are organized in a vibrant holder, and a soft area rug is placed on the floor.
Home in North Adams
4.99 out of 5 average rating, 165 reviews

North Adams Getaway-walk to MASS MoCA

BRAND NEW! Ready for guests to enjoy all the Berkshires has to offer! Whether you are visiting for work or pleasure, with family or friends this is a perfect place for you. Located in downtown North Adams you are surrounded by breath taking mountains and foliage, nestled between award winning museums, access to great food, and a short drive to ski resorts, breweries, Tanglewood, the highest peak in MA, and more. A true outdoorsman paradise. BOOK NOW!

Top guest favorite
A bright living area is highlighted by large windows offering expansive mountain views. A colorful abstract artwork hangs against a brick wall, framed by a green houseplant. A wooden coffee table sits atop a patterned rug, complemented by a cozy sofa and a wall-mounted TV.
Cottage in Williamstown
4.98 out of 5 average rating, 127 reviews

Artistic Nature Cottage

Kalarama Cottage is a newly renovated space in the middle of nature! Make yourself right at home in this quiet, private and peaceful location. The cottage is overlooking a beautiful forested mountain range, with easy access to hiking, biking, and cross-country ski trails right out the door. Kalarama is bright and sunny with stunning views. Come to unwind, enjoy nature, read, meditate or just work remotely from our 23 acre property!

Top guest favorite
A garden scene is presented with a wrought-iron chair nestled among frosted pink and green sedum flowers. A leafless tree stands in the background, framed by autumn foliage. Rolling hills are visible beyond the landscaped area, hinting at the surrounding natural beauty.
Apartment in Williamstown
4.98 out of 5 average rating, 115 reviews

ALL welcome: Lovely 1 BR studio, Berkshires beauty

Come as you are - we welcome ALL visitors. Relax and soak in your surroundings in this new 1 bedroom vacation spot. Part of a barn conversion, the space is clean and bright and ideally located for those exploring all the Berkshires has to offer. Perfect for an individual or couple looking to escape to a serene and beautiful setting - a stream abuts the property and hiking/snowshoeing trails are accessible out the front door.

Top guest favorite
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, 327 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 favorite
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, 339 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.

Popular amenities for Taconic Mountains vacation rentals