Vacation rentals in Hancock Shaker Village

4.97 out of 5 average rating, 110 reviews

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!

4.95 out of 5 average rating, 277 reviews

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

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

4.96 out of 5 average rating, 114 reviews

An open living space features a large sectional sofa surrounding a central glass coffee table. A decorative chandelier hangs from the exposed wooden beams. Natural light streams in through multiple floor-to-ceiling windows, revealing views of the surrounding greenery.

Barn in East Chatham

Luxury Barn Near Hudson with New Private Sauna

A secluded luxury barn retreat near Hudson and the Berkshires, now featuring a private sauna for year-round relaxation. Set on eight private acres where New York meets the Berkshires, this architect-designed 19th-century barn combines soaring ceilings, original beams and contemporary comforts. Enjoy a chef’s kitchen, two fireplaces, designer interiors, peaceful outdoor spaces and access to nearby Queechy Lake. Minutes from Chatham and an easy drive to Hudson, Great Barrington and Tanglewood.

4.95 out of 5 average rating, 42 reviews

Modern, Renovated Lakefront Escape

Evergreen Home Vacation Rentals invites you to the East Beach Lakehouse, a stylish, recently renovated retreat on the shores of Richmond Pond. Situated on over an acre of land, this stunning property features a private dock and guest watercraft for the ultimate lakefront experience. Enjoy the heart of the Berkshires from the screened porch or host a BBQ on the grill. With ample space and modern amenities, it’s the perfect setting for relaxation and water adventures. Book your lake escape!

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.

4.95 out of 5 average rating, 240 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!

4.94 out of 5 average rating, 207 reviews

A modern living area features large windows allowing natural light to fill the space. A cozy sofa and a comfortable chair invite relaxation, while a country-style table accommodates dining or work. The decor is enhanced by a colorful area rug and minimalistic furnishings.

Guest suite in Richmond

Berkshires/Pet Friendly/Tanglewood/Private Ranch

Pet-Friendly, Child-Friendly Getaway! Modern suite with full kitchen on private horse ranch. Wake to horses in the fields, hiking, breakfast on your patio. Perfect location for individuals, couples, families animal lovers. Near all ski areas (Jiminy Peak/Catamount/Bousquet /Butternut), shopping, museums (Norman Rockwell/Mass MoCA) wine tasting (Balderdash Cellars, Hilltop Orchards) Tanglewood, Jacobs Pillow, Miraval, Kripalu, Canyon Ranch. Trail Rides /Horse activities available by appt!

4.91 out of 5 average rating, 187 reviews

A wrap-around porch features a small table with two colorful chairs, overlooking a serene lake framed by lush trees and greenery. The view showcases calm water, complemented by distant hills under a clear blue sky.

Home in Canaan

Berkshire Lakefront House with Amazing Views

Enjoy the culture of the Berkshires & Hudson - 15 min from Tanglewood, Norman Rockwell Museum, Shakespeare & Co, PS21, McHaydn Theatre, Mount Greylock, Jiminy Peak Resort, zipline parks, Bousquet & more. Restaurants & market within driving distance and a membership-only beach within a short walk or drive. Great lake views with wrap-around porch. The lake is family-friendly. We welcome couples, solo adventurers, and families. Sorry, no "Group Bookings" - book & pay via one account only.

Earthen home in West Sand Lake

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.

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

5.0 out of 5 average rating, 57 reviews

Berkshires Colonial on 2 Acres by Evergreen Home

Evergreen Home Vacation Rentals invites you to this grand Colonial on 2.7 private acres in picturesque Richmond. This spacious home is the perfect base for quiet country living, located just 1 minute from Balderdash Cellars and 10 minutes from Bousquet Mountain. Enjoy effortless access to Tanglewood, apple picking, and world-class museums. Whether you're heading 30 minutes to Butternut or exploring local trails, this estate offers the ideal blend of tranquility and convenience.

Place to stay in New Lebanon

A kitchen features light blue cabinetry and a central island with a granite countertop. Above the island, open shelving displays decorative bowls and glassware. A dining table with wooden chairs is positioned nearby, while a cozy seating area is visible in the background.

20 minutes to Tanglewood

This property is like nothing you've ever seen--a gem near the top of Mt. Lebanon with 75 acres of forest, streams, waterfalls, gardens, and historic ruins on a former Shaker settlement. The newly renovated Caretaker's Cottage has 2 bedrooms, kitchen, living room, and bathroom. The Taconic and Berkshire mountains stretch out before the deck and screened-in porch. Berkshire and Hudson Valley restaurants, shops, and entertainment are all nearby. Owners on site if you need them.

5.0 out of 5 average rating, 37 reviews

5.0 out of 5 average rating, 27 reviews

Home in New Lebanon

Modernized 1860s Getaway w/ Queechy Lake Passes*

Unwind in our quiet, spacious, light-filled, rural home without leaving modern conveniences behind. Located in Historic Lebanon Springs, our newly restored antique home is near both Hudson Valley restaurants and shops and the Berkshire's vast outdoor activities. We took great care to save this home's historic details while creating a fully modernized, comfortable retreat. Every room is thoughtfully curated with local antiques, artwork, and many unique touches you'll enjoy.

The Mid-Century home presents a sleek, angular exterior with a flat roof and expansive glass windows. A green lawn stretches in front, bordered by trees. Red accent doors enhance the design, while a swing is positioned to the side, contributing to the serene outdoor environment.