Apartment vacation rentals in Berkshire County

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Top-rated apartment rentals in Berkshire County

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Guest favorite

Rental unit in Copake Falls

4.92 out of 5 average rating, 286 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!

Guest favorite

Rental unit in Petersburg

4.87 out of 5 average rating, 167 reviews

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Space is 14 x 28 feet and includes living/dining/work space, bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed with pull out twin mattress. High def TV, wifi, private deck, kitchenette has mini fridge, microwave, toaster oven, hot kettle for tea and and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

Guest favorite

Rental unit in Lee

4.78 out of 5 average rating, 115 reviews

Cozy Berkshire Cottage Style Apartment

Stay in a cozy Berkshires apartment! All new windows allow views to the peaceful surrounding state forest and yard. Watch humming birds, oriols, deer, squirrels, opossums, racoons, woodchucks, and more... The house is set back from the road, easily accessible, yet private. The cottage is a duplex: the Airbnb apartment is on the left side of the cottage. • Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Stockbridge, Lenox, MA Turnpike • Ideal for lovers of nature & the Berkshires

Superhost

Rental unit in Lanesborough

4.87 out of 5 average rating, 101 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

Guest favorite

Rental unit in Canaan

4.99 out of 5 average rating, 129 reviews

Mountain View Getaway

Come relax & enjoy panoramic mountain and pond views. Marvel at the dramatic lighting effects on Mercer Mt from sunrise-sunset from your private deck or bright living room. Fully equipped kitchen, grill on the deck, short scenic drive to a wide variety of restaurants & endless cultural venues in the surrounding quaint villages of Berkshire County Mass and Columbia County NY. Near hiking trails, skiing, apple picking & farm stores. Queechy Lake swimming, NYS boat launch for car top boats.

Guest favorite

Rental unit in Sheffield

5 out of 5 average rating, 337 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

Rental unit in Great Barrington

4.94 out of 5 average rating, 186 reviews

Secluded but not isolated Berkshire Retreat

1.5 bedroom 1.5 bath self contained apartment (apprx. 950 sq ft ) attached to the main house set on a secluded 5.5 acre lot 2.9 miles from downtown Great Barrington . There is a CB2 day bed in the living room that sleeps an additional 2 people comfortably. Extra charge of $25/night +tax if the extra bedroom is used in 2 person reservations. $20 extra cleaning fee for reservations of 4 or more. During heating season not suitable for children under 5 because of pellet stove. .

Guest favorite

Rental unit in North Adams

4.96 out of 5 average rating, 459 reviews

Steps to MoCA, 2bd + SAUNA!

This large 2 bedroom apartment occupies the entire parlor floor of the Small Mansion of Chase Hill, 3 minutes by walk to Mass MoCA. A 5 mins walk to downtown’s restaurants. 5-10 mins drive to Williams, Clark, Windsor Lake, Cascade Waterfalls and many more of the attractions Berkshires have to offer. Whimsically restored (yes, fast Wi-Fi & great water pressure). Part of @chasehillartistretreat. YOUR STAY ENABLES US TO HOST REFUGEE/IMMIGRANT ARTISTS PRO BONO!

Guest favorite

Rental unit in New Lebanon

4.95 out of 5 average rating, 130 reviews

Sunny Duplex at the old boarding house

Charming big vintage apartment for up to a family of five in an old boarding house from 1900. It's a Greek Revival house on a country lane at the foot of the Berkshires. Master bedroom and full bath are downstairs, where there is also a lovely living room, fully stocked kitchen and mudroom with washer/dryer. 2nd bedroom and side room in the attic upstairs. Small front sitting porch, big side lawn and flowery backyard with grill and table.

Guest favorite

Rental unit in Lee

5 out of 5 average rating, 114 reviews

Lovely Berkshire apartment with beautiful views

Kick back, relax and rejuvenate in this calm, stylish, zen new space minutes from town. Private entrance with keyless entry. Comfy crisp clean beds and spacious living room. Kitchen has everything you'll need to cook dinners or not! Friends getaway, couples, familes or remote work. Mountain views and beautiful sunsets Minutes to Tanglewood/Jacobs Pillow

Guest favorite

Rental unit in Great Barrington

4.95 out of 5 average rating, 342 reviews

Private En Suite in Beautiful Victorian

The room is light and airy with morning sun and the shade of the large front porch in the afternoon. This is a place to enjoy a meal or just lounge and relax with a view of the gardens and surrounding woods. This space features a private entrance, a kitchenette and full bathroom and very comfortable queen bed. In mid July 2024 we added air conditioning.

Guest favorite

Rental unit in Williamstown

4.93 out of 5 average rating, 271 reviews

COLD SPRING

This cozy, quaint and quiet apartment offers the perfect Berkshire county getaway. Just a drive away from Mount Greylock National Park, Jiminy Peak Mountain Resort, and the Tony-Awarded Williamstown Theatre Festival. Enjoy the mountain views, in this two bedrooms 1 bath rental with fully equipped kitchen and skylight vaulted ceiling.