Apartment vacation rentals in Berkshire County

King Bed | Stylish | Wi-Fi | *2m Ski Resort*

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv with Hulu Live

Location · Family · Checkout

Historic,Famous,Iconic, Unforgettable Berks Escape

PICTURE IT...You can put yourself in the "famed" Norman Rockwell Main Street at Christmas Painting! That's Right,Cozy, Intimate,Magical and all to yourself.Fully equipped with all the comforts of home. Small Town Charm,Big time Historic setting in the heart of Downtown Stockbridge! Spend your afternoon sipping Tea or Wine looking out the iconic picture window Norman Rockwell installed himself. The one where the Christmas Tree Glows in a room that was Norman Rockwell's Studio from 1953-1957

Family · Location · Accuracy

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.

Location · Value · Kitchen

Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

Location · Family · Solo travel

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! Note: there is no TV.

Location · Value · Solo travel

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.

Location · Family · Solo travel

Charming Farmhouse Apt Near Williams College

Relax in this charming New England farmhouse apartment just minutes from Williams College, Mass MoCA, and downtown Williamstown. This private second-floor retreat features original wood floors, a spacious bedroom with a comfortable queen bed, a fully equipped kitchen, and a peaceful setting perfect for couples, Williams College visitors, and Berkshire escapes. Enjoy easy access to local restaurants, hiking trails, museums, and the best attractions throughout the Berkshires.

Value · Family · Biking

The MoCA-Cabana: 2 bd + Sauna

Welcome to the MoCA-Cabana at Chase Hill—the historic estate of the owners of the factory that became MASS MoCA. More than just guest houses, Chase Hill is an experience: gardens, fire pits, sauna, occasional music rehearsals. Just a 5-minute walk to MASS MoCA, 10 mins by car to Williams & Clark. ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates often available beyond what the calendar shows—don’t hesitate to contact us!

Value · Location · Kitchen

Marie's Place

This newly renovated bright sunny apartment is minutes from Bosquet ski area & also close to downtown. It has a large kitchen and pantry. Beautiful oak dining room table. Comfy living room set, with a 43 inch Roku TV. Electric fireplace. Queen size beds in both bedrooms. Large walk-in closet in. Large bathroom with tub and shower. 28 minutes from Jiminy peak. Close to downtown restaurants and theaters. Ac units are installed from June through September.

Value · Location · Grill

Lovely Downtown Lenox apt, walk to everything!

Experience the best of the Berkshires in a beautiful, spacious apartment right in the center Lenox. This updated space is filled with natural light and hardwood floors, great for families or friends looking to experience culture and countryside. Walking distance to Tanglewood, Shakespeare & Co, Kennedy Park, restaurants, and shopping. On second floor of a Historic building with a deck that has a birds eye view of town. 7 min to Bousquet Mountain.

Location · Family · Accuracy

Historical Downtown 1 Bedroom Apartment

Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for two, stainless appliances, and an array of cooking essentials. The living room features a comfortable sectional and a flat screen TV for relaxing. Wi-Fi is available throughout the space. Central heat and air to provide a comfortable environment in any season. All linens and towels are provided.

Location · Family · Cleanliness

Airy apartment at the old boarding house

Distinctive 2-bedroom with lots of windows and light and a kind of shabby elegance. It's half of a Greek Revival house from 1900 on a country lane at the foot of the Berkshires. Enormous master bedroom with dressing room, 2nd bedroom with twin beds, lovely living room, separate dining room, full kitchen. Big covered front porch for eating outside, with grill, table and an acre of orchard outside too.

Family · Location · Getting around