
Places to stay near Mount Greylock
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Top-rated holiday rentals near Mount Greylock
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Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

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.

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!

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!

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.

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!

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.

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.

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.

Schoolhouse Spa Retreat on a Vermont Farm
Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

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.

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.
Popular amenities for holiday rentals near Mount Greylock
Apartment rentals with wifi

Beautiful condo 2.5 miles from Mount Snow

Mountain Getaway @ Seasons on Mt Snow (Ski-In/Out)

Mt Snow Ski In/Out at Seasons

Winter Dream! The Handle Lodge at Snowtree Condos

Owl's Nest - Unique Condo in Vintage Location

Elegant, spacious studio apt in historic mansion

Great 2 bedroom condo at Stratton Mountain

Cozy condo within walking distance to the slopes.
Family-friendly house rentals

Quality, Comfort, Charm in Williamstown Center

Mountain Escape: Spring and Summer Specials!

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

Idyllic family retreat - spacious lake home,

Cantabile life in the Berkshires

19th c. Barn in The Berkshires

1890 House

The old sawmill from 1771
Apartment rentals with air conditioning

Charming Art Filled Apartment

Sunny, light filled loft in 1873 Colonial

Shakespeare’s Folly Side Farm and AirBnB.

Berkshire Mountain Top Chalet

Suite 23 - Spacious Sunny 2-BR with Mountain view

The Beer Diviner Brewery Apartment

COLD SPRING

Hudson River Beach House
Other great holiday rentals near Mount Greylock

Barn Stay at Shadowbrook Farm

Cute Cozy Comfy Cottage in the Berkshires

Dog Friendly Studio

Secluded cabin with babbling brook

Berkshire Guest Suite

T’Other House

Cozy, bright 3-bedroom Cottage with fireplace.

Mountain Retreat close to Northampton & Amherst!
Destinations to explore
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Butternut Ski Area and Tubing Center
- Thacher State Park
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Saratoga Spa State Park
- Taconic State Park
- Norman Rockwell Museum
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Naumkeag
- National Museum of Racing and Hall of Fame
- June Farms
- Berkshire Botanical Garden
- Hancock Shaker Village
- Emerald Lake State Park
- New York State Museum




