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Apartment vacation rentals in Berkshire County

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Berkshire County

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A living area is visible, featuring a sleek gray couch and a modern chair positioned near a stylish fireplace. Artwork is displayed on the wall, and natural light illuminates the space. A neutral rug adds texture to the polished floor, with a bedroom area partially seen in the background.
Apartment in Copake Falls
4.9 out of 5 average rating, 352 reviews

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!

Top guest favorite
A winter scene depicts a charming town square with snow-covered ground, featuring a building adorned with a glowing Christmas tree in its window. Vintage cars are parked in front, while small groups of people are visible, creating a festive atmosphere against a twilight sky.
Apartment in Stockbridge
4.96 out of 5 average rating, 114 reviews

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

Guest favorite
A wooden sign with a circular cutout features the name 'Second Drop Farm' prominently displayed in metallic letters. Inside the circle, a metal silhouette of a tree is depicted, showcasing intricate branches and roots against a rustic wooden background.
Apartment in Lanesborough
4.9 out of 5 average rating, 138 reviews

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

Top guest favorite
A spacious living area features comfortable seating, a glass coffee table, and a dining space with wooden chairs. The kitchen is visible, showcasing modern appliances and a light wood countertop. Natural light illuminates the room, creating a warm and open atmosphere.
Apartment in Sheffield
5 out of 5 average rating, 382 reviews

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.

Guest favorite
A modern bedroom is presented, featuring a plush king-sized bed with crisp white linens. A sliding glass door allows access to an outdoor space, while a small table and decorative items add to the aesthetic. A dark accent wall provides depth, complemented by natural light.
Apartment in Great Barrington
4.92 out of 5 average rating, 130 reviews

King Bed |Wi-Fi| 2m to 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 KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *58" TV w/ Hulu + Live

Guest favorite
The kitchen area features a black refrigerator and a round wooden dining table surrounded by two matching chairs. Natural light enters through a window, illuminating the space with a bright and airy feel. A door leads to another room, adding functionality.
Apartment in Williamstown
4.94 out of 5 average rating, 116 reviews

Williamstown apt close to Williams College & MoCA.

Second floor 1 bedroom (Queen) and 1 bathroom apartment with private entrance. This cozy Williamstown retreat will provide exactly what you would expect in the Berkshires. Walking distance to downtown Williamstown and the newly created bike path. This unit provides off street parking with plenty of privacy, and can truly transform your stay. Less than 5 Miles to MASS MoCA. 25 Minutes to Jiminy Peak. 1.5 Miles exactly to the center of Spring St. .4 Miles to the bike path entrance.

Top guest favorite
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.
Apartment in Petersburgh
4.89 out of 5 average rating, 202 reviews

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.

Top guest favorite
A large Victorian house is framed by vibrant autumn foliage, with colorful orange, yellow, and red leaves. The home features a spacious porch and multiple gabled roofs, blending harmoniously with the surrounding nature and the peaceful landscape.
Apartment in North Adams
4.96 out of 5 average rating, 621 reviews

Steps to MoCA: 2bd + SAUNA!

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. Closest ⛷️ SKI resorts are Jiminy Peak and Berkshire East Mountain. Whimsically restored (yes—fast Wi-Fi & great water pressure!) and part of @chasehillartistretreat. ✨ Your stay supports pro bono residencies for refugee & immigrant artists.

Guest favorite
A spacious front porch is framed by white columns and features two seating areas. Lush greenery encompasses the porch, with a flowering rhododendron bush in the foreground. The blue sky is dotted with clouds, enhancing the inviting atmosphere of the outdoor space.
Apartment in New Lebanon
4.96 out of 5 average rating, 114 reviews

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.

Top guest favorite
A red barn-style building is illuminated at night, featuring two large garage doors at ground level and two windows above. The light from the windows hints at the warm interior, while the surrounding area remains dark, creating a serene and inviting ambiance.
Apartment in Sheffield
4.93 out of 5 average rating, 164 reviews

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.

Guest favorite
The exterior of a two-story blue apartment building is depicted, featuring a covered porch and welcoming entrance. Two parked cars are visible in the driveway, with green lawns and trees nearby. Window flower decorations add a touch of charm to the façade.
Apartment in Adams
4.87 out of 5 average rating, 152 reviews

full apartment in adams self check in

nice apartment on first floor in adams mass near mt greylock(URL HIDDEN) also 2 miles to greylock glen at the base of the mountain for hiking & biking trails 5 miles from mass moca 5 miles from mcla 12 miles from clart art & williams college 10 miles mt greclock peak 18 miles from jiminy peak , a ten mlle bike trail about 1000 feet from house also 23 miles & 40 minutes to tanglewood

Guest favorite
An inviting entrance area showcases a vintage Coca-Cola vending machine. A wooden door leads into a room with a detailed patterned wallpaper. A decorative stove stands prominently, complementing the warm aesthetic of the space.
Apartment in Lenox
4.88 out of 5 average rating, 198 reviews

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.

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