
Apartment vacation rentals in Berkshire County
Find and book unique apartments on Airbnb
Top-rated apartment rentals in Berkshire County
Guests agree: these apartments are highly rated for location, cleanliness, and more.

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! 7 min walk to nearest hiking trail!

King Bed|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

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

Walk Everywhere! | Relax in Easy Elegance!
Gracious in-town apartment feels like home--with a living and dining room, full kitchen, 2 bedrooms and 2 baths all just for you and your group. A one-minute walk to shops, restaurants, theaters, food co-op, and farmers’ market, and a short drive to Berkshire arts offerings and spectacular hiking and skiing areas. Or treat yourself to a spa day at Kripalu, Body&Soul or Michele's Salon, among others. Spectrum WiFi; no TV; plenty of books, games, indoor space to spread out and outdoor areas.

Cozy Rustic Apt. in 18th c. Berkshire Farmhouse
This cozy rustic studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in the 1700’s, this centuries old farmhouse has since been converted into four separate cute suites. Newly updated kitchen, bathroom and furniture. Enjoy exploring the sprawling 19 acre property you will be staying on which includes seasonal flower fields, thousands of berry bushes, fruit trees, creek, and walking trails full of wildlife. Follow us on IG @SecondDropFarm

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.

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.

Steps to MoCA: 2bd + SAUNA!
Enjoy peak autumn foliage in the Berkshires—now through early November! A spacious, private two-bedroom at the Small Mansion of Chase Hill Estate in North Adams. Just 3 minutes to MASS MoCA, 5 minutes to downtown restaurants, and 10 minutes to Williams College or The Clark. Whimsically restored (yes—fast Wi-Fi & great water pressure!) and part of @chasehillartistretreat. ✨ Your stay supports pro bono residencies for refugee & immigrant artists.

Downtown | Waterfront | Walk to Shops
★ New to Williamstown? Explore our interactive guidebook. One bedroom with all the bells and whistles! 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.

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.

Private Berkshire Barn Apartment
A private entrance and apartment all to yourself. You are within a 2 minute drive of downtown Sheffield or a 10-15 minute walk. Also within a short drive of superb restaurants and local ski areas, Great Barrington, Tanglewood, Jacobs Pillow, The Rockwell Museum and numerous other Berkshire attractions. Also within a short drive of Berkshire, Salisbury, Hotchkiss and Simon's Rock schools.

Station House 1E Private Room & Bath
Our place is a central location in Berkshire County, short drive to restaurants and shops; art and culture, skiing and hiking also close by. You’ll love this former train station( next to the Housatonic RR tracks) which is on three acres between a chapel, the scenic Housatonic River and October Mountain. Our place is good for couples, solo adventurers, and business travelers.
Popular amenities for Berkshire County apartment rentals
Weekly apartment rentals

Writer/Reader Retreat: library, fireplace, study

Cute, Cozy and Comfortable apartment

Zen River Studio

Center of Lenox, cozy Apartment 2-bedroom

Eliza Suite

Three bedroom duplex in Stockbridge on the river

The Penthouse, Downtown Lenox by Evergreen Home

Comfy Quaint Tavern
Private apartment rentals

Downtown Apartment A

Beautiful Apartment in Central Pittsfield

Berkshires Apartment @ the Stephentown Hotel

North Adams | MASS MoCA | 3 BRs | Parking + W/D

"Nostalgia" a spacious2 bedroom first floor unit.

Cozy Berkshires pied-a-terre

Downtown Jewel | Stylish | Fully Stocked | Firepit

Charming 2-Bedroom Suite (Private Entrance)
Apartment rentals with a hot tub

Mountainside Condo Ski on/off

Dream Vacation

Ski-InSki-Out Loft Lift&MT.Views

Cozy Ski Retreat

1 Bedroom Deluxe @ Wyndham Bentley Brook

Luxe Ski Getaway Base of Jiminy

Artsy loft surrounded by fall foliage with hot tub

The Crystal Loft
Destinations to explore
- Hotel rentals Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Guesthouse rentals Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Rentals with a patio Berkshire County
- Family-friendly rentals Berkshire County
- Rentals with a washer and dryer Berkshire County
- Rentals with a fire pit Berkshire County
- Rentals with a kayak Berkshire County
- Fitness-friendly rentals Berkshire County
- Rentals with a fireplace Berkshire County
- Rentals with pools Berkshire County
- House rentals Berkshire County
- Cottage rentals Berkshire County
- Rentals with breakfast Berkshire County
- Farmstay rentals Berkshire County
- Condo rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Pet-friendly rentals Berkshire County
- Bed and breakfasts Berkshire County
- Waterfront rentals Berkshire County
- Beachfront rentals Berkshire County
- Rentals with lake access Berkshire County
- Private suite rentals Berkshire County
- Aparthotel rentals Berkshire County
- Rentals with a sauna Berkshire County
- Rentals with beach access Berkshire County
- Chalet rentals Berkshire County
- Rentals with an EV charger Berkshire County
- Apartment rentals Massachusetts
- Apartment rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Zoom Flume
- Catamount Mountain Ski Resort
- Bushnell Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Taconic State Park
- Mount Sugarloaf State Reservation
- Opus 40
- Mohawk Mountain Ski Area
- Beartown State Forest
- Mount Tom State Reservation
- Mount Snow Ski Resort
- Bousquet Mountain Ski Area
- Hartford Golf Club
- Bright Nights at Forest Park
- Albany Center Gallery
- Talcott Mountain State Park