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Places to stay near Mount Greylock

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Top-rated holiday rentals near Mount Greylock

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

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Top guest favourite
Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

4.97 out of 5 average rating, 110 reviews
Top guest favourite
Treehouse in Wilmington

Beautiful timber-frame treehouse

The timber frame treehouse is a perfect couples retreat. The home is custom built with hardwood maple trees cut down and milled right on the property. The deck has a barrel sauna, cold or hot cedar soaking tub, a propane fire pit, a wood burning chiminea fire pit, and a bar top for outdoor dinning. The inside has a stone fireplace, fully equipped kitchen, tile shower, projector with dvds, books, board games, chandelier, and dimmable lighting for any mood. This home is truly one of a kind.

5.0 out of 5 average rating, 124 reviews
Guest favourite
A spacious mountain lodge is depicted, featuring a striking stone chimney and expansive decks. Large windows frame the scenic landscape, while lush green grass surrounds the building. The warm tones of the log exterior harmonize with the natural setting, inviting outdoor relaxation.
Flat in North Adams

Berkshire Mountain Top Chalet

Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.

4.93 out of 5 average rating, 193 reviews
Guest favourite
The entrance to a Hobbit house is framed by lush greenery and natural stone. A curved, grassy roof merges with the surrounding trees, while a stone pathway leads to the large wooden door. Decorative lanterns are positioned above the entrance, enhancing the rustic charm.
Earthen home in West Sand Lake

The Hobbit House at June Farms

Watch June Farms on Amazon Prime Video! Enjoy 120-acres of beautiful farmland while you stay in your very own Hobbit house! Nestled in the hills of Hudson Valley, June Farms is a gorgeous animal sanctuary. During your stay, you will be able to meet our Shire horses, Highland cows, spotted pigs, Nigerian dwarf goats, many chickens and ducks! From June 1 - Labor Day, the bar & restaurant is open most days for you to enjoy (check our calendar to be sure). We look forward to meeting you!

4.97 out of 5 average rating, 256 reviews
Guest favourite
Flat 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!

4.97 out of 5 average rating, 734 reviews
Guest favourite
A view of the urban cabin surrounded by greenery, showing the rolling hills of the Hoosac Range in the background. The cabin is complemented by lush foliage and trees, creating a serene atmosphere, while the townscape can be seen in the distance.
Home in North Adams

Colorful Urban Cabin Steps from Mass MoCA

Enjoy the best of the Berkshires from this charming urban cabin: easy access on foot to North Adams' restaurants, bars, and Mass MoCA, plus panoramic views of the Hoosac Range from the front porch and backyard. Easy drives to hiking, swimming, skiing and the rich cultural amenities of the region. Please note: the ceiling is a little low in a few places. Anyone 6'3 or taller will want to watch their head in a few places, including getting in and out of the shower.

4.88 out of 5 average rating, 116 reviews
Top 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

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.

4.91 out of 5 average rating, 149 reviews
Superhost
A uniquely designed raised container home features multiple levels and large windows that offer expansive views of the surrounding landscape. The structure includes a covered outdoor area below, and the combination of dark wood and metal creates a striking exterior appearance.
Shipping container in Whitingham

The House of Pi

WE now pay your 15.5% Guest Service fee!!! Welcome to The House of Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock and Kayaks. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Hot Tub and Custom Cedar Sauna!

4.88 out of 5 average rating, 124 reviews
Top guest favourite
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

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!

4.99 out of 5 average rating, 225 reviews
Top guest favourite
A modern kitchen is equipped with stainless steel appliances, including a refrigerator and oven. White cabinetry offers ample storage. A central island features a sink and prep space, complemented by a set of kitchen utensils. Natural light enters through a nearby window.
Flat in Williamstown

Downtown | Waterfront | Walk to Shops

★ New to Williamstown? Explore our interactive guidebook. One bedroom apartment, meticulously upgraded with the discerning guest's convenience in mind. The property is in the midst of Williamstown's popular spots: Williams College campus, theaters, museums, restaurants, shops, and golf course. It also sits by the rushing, sometimes tranquil, Green River where you can sit back, relax and enjoy the fire pit.

5.0 out of 5 average rating, 171 reviews
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

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.

4.97 out of 5 average rating, 353 reviews
Top guest favourite
The light-filled living room features a comfortable gray couch with decorative pillows, a vintage coffee table, and an eclectic mix of artwork on the walls. A television is positioned on a wooden stand, and diverse seating options are provided by antique chairs and a small dining table.
Flat in North Adams

Charming Art Filled Apartment

Charming and quirky, this 2nd floor apartment in a 120 year old house is decorated with art and antiques, like the living museum of an eccentric friend. Or a mini theme park for the mind. We are just blocks from downtown North Adams, on the main road into town. It’s literally a 2 minute drive to MASS MOCA, or a ten minute walk. Dogs are always welcome!

4.98 out of 5 average rating, 201 reviews

Popular amenities for holiday rentals near Mount Greylock

KitchenWifiPoolFree parking on premisesAir conditioning

Other top sights near Mount Greylock

Mount Snow

362 locals recommend

Norman Rockwell Museum

483 locals recommend

Hancock Shaker Village

231 locals recommend

Mount Greylock

308 locals recommend

Naumkeag

187 locals recommend

Berkshire Botanical Garden

185 locals recommend

Apartment rentals with wifi

Guest favourite
A snowy landscape is presented, showcasing ski slopes and a bustling scene below. A quaint building serves as a backdrop, surrounded by skiers and snowboarders. Tables and chairs are visible, along with ski equipment neatly arranged, highlighting the active atmosphere accessible from the condo.
Apartment in Hancock

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1

4.93 out of 5 average rating, 103 reviews
Guest favourite
Apartment in Albany

Elegant, spacious studio apt in historic mansion

4.89 out of 5 average rating, 368 reviews
Top guest favourite
Apartment in Dover

Winter Dream! The Handle Lodge at Snowtree Condos

4.99 out of 5 average rating, 136 reviews
Guest favourite
Apartment in Dover

Base of M.S. All Seasons Fun. Deck/HotT/Sauna

4.92 out of 5 average rating, 128 reviews
Guest favourite
A spacious living area is depicted with a large sectional sofa and a wooden coffee table. A stone fireplace serves as a focal point, featuring a mounted TV above. Natural light streams through the windows, illuminating bookshelves filled with games and books, while a stack of firewood is neatly arranged beside the fireplace.
Apartment in Dover

Slopeside @ Seasons on Mount Snow (Ski-In/Out)

4.92 out of 5 average rating, 105 reviews
Top guest favourite
Apartment in Stratton

Premier Stratton Village Location - Pool & Hot Tub

4.97 out of 5 average rating, 214 reviews
Guest favourite
A spacious living area is introduced, featuring a stone fireplace and a large sectional sofa arranged around a coffee table. A dining table and chairs are positioned nearby, with natural light filtering through large windows adorned with curtains.
Apartment in Dover

Great Amenities-Season Condo gym-sport center-pool

4.94 out of 5 average rating, 107 reviews
Superhost
A spacious living area is highlighted by large windows that provide a panoramic view of the surrounding hills. The room features a comfortable sofa, a wooden coffee table, and a dining set. A fireplace and a fully equipped kitchen are situated in the background.
Apartment in Stratton

~10% OFF~Walk To Mountain~Amenities

4.88 out of 5 average rating, 112 reviews

Family-friendly house rentals

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

19th c. Barn in The Berkshires

4.85 out of 5 average rating, 230 reviews
Guest favourite
Home in Adams

1890 House

4.92 out of 5 average rating, 271 reviews
Top guest favourite
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

4.93 out of 5 average rating, 213 reviews
Top guest favourite
A light-colored one-story house is set against a backdrop of trees. A wooden deck extends across the front, providing access to the entryway. The yard features well-maintained green grass and shrubs, contributing to a welcoming exterior.
Home in North Adams

Bernie's & Betty's

4.97 out of 5 average rating, 197 reviews
Top guest favourite
A pathway lined with lush greenery leads to a bungalow with a screened-in porch, featuring outdoor seating. The soft sunlight filters through the foliage, creating a serene entrance to the welcoming space.
Home in Williamstown

Hollywood Bungalow in the Berkshires #C0191633410

4.9 out of 5 average rating, 242 reviews
Top guest favourite
A welcoming living area is seen through an arched doorway. Two patterned chairs sit beside a small table, illuminated by soft light. A bookshelf filled with books lines the wall, while a traditional rug adds color to the wooden floor. An antique clock stands nearby.
Home in Ashfield

An 18th century farmhouse

4.97 out of 5 average rating, 110 reviews
Top guest favourite
A white farmhouse-style structure is set on a lush green hill, surrounded by a clear blue sky. The building features a gabled roof, multiple windows, and a small cupola. A neat lawn frames the house, emphasizing its inviting exterior.
Home in Bennington

Cozy Modern Sugar House with spectacular views.

4.99 out of 5 average rating, 358 reviews
Guest favourite
A spacious living area features a warm wood-paneled ceiling and modern furnishings. Two sleek sofas are arranged around a wooden coffee table, while armchairs provide additional seating. Natural light floods the space through large windows framed by light curtains, enhancing the welcoming atmosphere.
Home in Cheshire

Large Secluded Berkshire Home

4.81 out of 5 average rating, 167 reviews

Apartment rentals with air conditioning

Top guest favourite
The exterior of a two-story purple house is featured, showcasing a wrap-around porch with white rocking chairs and a small table. Large windows allow ample natural light, while a green planter hangs near the entrance, surrounded by lush foliage.
Flat in North Adams

"Nostalgia" a spacious2 bedroom first floor unit.

4.96 out of 5 average rating, 106 reviews
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.
Flat in Williamstown

Cold Spring - The White Door

4.94 out of 5 average rating, 370 reviews
Guest favourite
The living area features warm wooden floors and a cozy seating arrangement, including a sofa and an armchair. Light pours through the window, illuminating a colorful area rug and a coffee table adorned with books. A pair of opened doors leads to the spacious bedroom, showcasing a bed with decorative bedding.
Flat in North Adams

Private guest apartment. One block from downtown.

4.91 out of 5 average rating, 512 reviews
Guest favourite
Flat in Williamstown

Charming Farmhouse Apt Near Williams College

4.94 out of 5 average rating, 135 reviews
Top guest favourite
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.
Flat in Petersburg

The Beer Diviner Brewery Apartment

4.9 out of 5 average rating, 235 reviews
Guest favourite
A cozy bedroom is filled with natural light from two windows, dressed with blue curtains. A spacious bed with striped bedding is centered in the room. A white dresser and a television are positioned along the walls, creating a relaxing atmosphere.
Flat in Stamford

Getaway Near Mass MoCA, Great Hiking, Scenic Views

4.88 out of 5 average rating, 360 reviews
Top guest favourite
A modern kitchen features a central island with bar stools, stainless steel appliances, and white cabinetry. Natural light floods the space through a skylight and large windows, highlighting the open layout. A dining area with dark chairs sits adjacent to the kitchen.
Flat in Charlemont

Suite 23 - Spacious Sunny 2-BR with Mountain view

5.0 out of 5 average rating, 201 reviews
Top guest favourite
The exterior of the condominium building is highlighted, featuring a two-story design with a light blue facade. Lush greenery surrounds the property, enhancing the natural setting. A gravel pathway leads to the entrance, and outdoor seating areas are visible in the landscaped garden.
Flat in North Adams

Overlooking the city in a quiet 7 unit building.

4.99 out of 5 average rating, 221 reviews

Other great holiday rentals near Mount Greylock

Guest favourite
A comfortable living area features a light gray sectional sofa and an accent chair, accompanied by a sleek coffee table. Large windows allow natural light to fill the space, which is complemented by a textured area rug and a modern floor lamp.
Flat in Williamstown

House on the Town Green

4.98 out of 5 average rating, 150 reviews
Top guest favourite
The spacious studio features a light-filled sleeping area with a queen-sized bed, a nightstand, and a large dresser. Wooden beams accent the walls, and a full-length mirror reflects the natural light from the large window, overlooking a serene outside view.
Guest house in Williamstown

Peaceful/modern post and beam studio apartment

4.97 out of 5 average rating, 191 reviews
Top guest favourite
The A-frame house is framed by tall trees, featuring large triangular windows that enhance natural light. A wooden deck extends to a seating area with two rocking chairs and a picnic table. A person walks their dog along the path leading to the entrance.
Place to stay in Stratton

The Chal-A-Frame Vermont

4.99 out of 5 average rating, 225 reviews
Top guest favourite
A charming small home is presented, featuring a welcoming front porch with steps leading to the entrance. Lush green grass surrounds the house, accentuated by colorful flowering shrubs. Tall trees provide shade, while a gravel driveway provides access to parking.
Cottage in Williamstown

Charming Williamstown Cottage

4.99 out of 5 average rating, 148 reviews
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

Berkshire Guest Suite

4.96 out of 5 average rating, 270 reviews
Guest favourite
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford

Vermont Mirror House

4.95 out of 5 average rating, 161 reviews
Top guest favourite
A classic log cabin stands surrounded by greenery, featuring a spacious front porch with a wooden railing. Large windows dominate the front, allowing natural light to fill the interior. An American flag is displayed, adding to the rustic charm of the structure.
Cabin in Plainfield

Peaceful Cabin in the Woods

4.92 out of 5 average rating, 258 reviews
Guest favourite
An open living space with a high wood-beam ceiling is displayed. A large stone fireplace serves as a focal point, surrounded by comfortable seating. A kitchen island with stools offers additional space. Large windows allow natural light to fill the room, enhancing the inviting atmosphere.
Farm stay in New Lebanon

Barn Stay at Shadowbrook Farm

4.95 out of 5 average rating, 277 reviews