Places to stay near Mount Greylock

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Top-rated vacation rentals near Mount Greylock

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Top guest favorite
The living area features wooden walls and ceiling beams, creating a cozy environment. A brown leather sofa with patterned cushions faces a rustic wooden coffee table. A dining area with four bar stools is visible in the background, along with a well-equipped kitchen area.
Cabin in Florida
4.96 out of 5 average rating, 132 reviews

Florida Mountain Log Cabin

Best ski condition and located on the snowmobile trail! Enjoy this stylish custom built 3 BR, 1Full Bath log cabin with a full kitchen on top of Florida Mountain. Outdoor oasis (weather permitting): Firepit, string lights, grill, and the lovers' swings! Conveniently located on the Mohawk Trail and 15 min to Berkshire East. Within an hour from Mt. Snow & Jimminy Peak. Great WiFi and cell reception. Close to North Adams, Williamstown & Deerfield River. Nature, art, and outdoor activities nearby.

Top guest favorite
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, 313 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 favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 357 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
Home in Adams
4.99 out of 5 average rating, 102 reviews

Family-friendly historic charm w/ modern amenities

Experience the best of the Berkshires in our cozy, family-friendly retreat! Warm up by the fireplace, enjoy a fully stocked kitchen, and relax in four comfy bedrooms and two bathrooms. Step outside for skiing or hiking adventures by day and stunning sunsets by evening with mountain views in every direction. Walking distance to downtown Adams, drive to museums, hiking, skiing, shopping, sightseeing, and more! Perfect for families, couples, or friends seeking a peaceful countryside escape!

Top guest favorite
A spacious living area features high vaulted ceilings with exposed wooden beams and large skylights. Natural light illuminates the modern decor, including a comfortable couch, sleek bar stools, and a central coffee table. A fireplace is positioned beside expansive windows that offer views of the surrounding forest.
Cabin in Shaftsbury
4.99 out of 5 average rating, 315 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, 114 reviews

The Vermont Farmhouse|Hiking|Dog Trails|Village

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.

Guest favorite
Home in Adams
4.92 out of 5 average rating, 262 reviews

1890 House

Back online after renovations. This beautiful Victorian farmhouse is situated on a 1/2 acre with great views of Mount Greylock, surrounding mountains and quaint town of Adams. The wraparound porch is perfect for relaxing. It is fully furnished and has a fully equipped kitchen. There is a wood stove in living room. Walking distance to Adams/supermarket. Short drive North Adams (MASSMoCA), Williamstown (Clark Museum) and Jiminy Peak (ski resort) which is 30 minutes drive.

Top guest favorite
A tiny home features a private hot tub on the deck, illuminated by soft LED lights. The structure is surrounded by natural wood paneling, with doors leading into the cozy interior, where warm light spills out, creating an inviting ambiance.
Tiny home in Chatham
4.99 out of 5 average rating, 342 reviews

Boutique TINY home+private HOT TUB-walk to Main St

March-April midweek special: Bottle of prosecco, robes/slippers, s'mores. Boutique-luxe tiny home with private hot tub, firepit, and dreamy loft lounge. Plush queen bed, full kitchen, and curated charm throughout. A peaceful & private oasis, yet just a 2-min walk to Chatham’s Main St. lined with restaurants, brewery, shops & theater. The perfect upstate NY getaway for couples—hike, visit galleries, stroll to dinner, or unwind in your own private spa oasis @artparkhomes.

Top guest favorite
Apartment in North Adams
4.98 out of 5 average rating, 683 reviews

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!

Guest favorite
Tiny home in New Marlborough
4.95 out of 5 average rating, 154 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Guest favorite
A historic Victorian home is presented with multiple levels and large, decorative windows. The white exterior is complemented by a wraparound porch adorned with railings. Lush greenery surrounds the house, enhancing the inviting front entrance, while flowering shrubs add a touch of color to the landscape.
Guest suite in Adams
4.87 out of 5 average rating, 119 reviews

Quaint Suite in Center of Adams

Pet Friendly mother-in law suite within a beautiful Victorian home in the center of Adams. The quaint town sits at the base of Mount Greylock with hiking and bike trails within minutes of your accommodations. Restaurants, grocery store and a 9 hole golf course are in walking distance. MASS MOCA is just a short 6 mile drive. Tanglewood music center is a 35 minute drive. Beautiful deck with gas firepit and grill. We would love you to be our guest.

Top guest favorite
Cottage in Bennington
4.98 out of 5 average rating, 112 reviews

Cozy, bright 3-bedroom Cottage with fireplace.

Cozy, spacious brook-side cottage with 3 bedrooms, 2 baths, fully-equipped kitchen, fireplace, and serene, 382-acre country setting. Colorful artwork, designer furnishings, and well-appointed kitchen and bathrooms will make you feel welcome and at home. Historic charm of Bennington ten minutes away. NYC (182 miles); Boston (118); Mt. Snow (32); Prospect Mountain (13). Close to MASS MoCA (22), Tanglewood (49) and Manchester outlets (32).

Popular amenities for vacation rentals near Mount Greylock

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Berkshire County
  5. Adams
  6. Mount Greylock