Apartment vacation rentals in Berkshire County

Apartment in Copake Falls

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.

4.91 out of 5 average rating, 323 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!

Apartment in Great Barrington

A cozy living area is furnished with a white sofa and two armchairs. A wooden coffee table sits in the center, adorned with a book. Light filters through bay windows, enhancing the warm wooden floors and vintage decor.

5 out of 5 average rating, 118 reviews

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.

Apartment in Great Barrington

The living room features a large, comfortable sofa and a day bed, providing multiple seating areas. An abstract painting adorns one wall, and a flat-screen TV is positioned nearby. Natural light enters through the windows, illuminating the wooden flooring.

4.93 out of 5 average rating, 193 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. .

4.95 out of 5 average rating, 131 reviews

A cozy living room features a brown leather sofa adorned with various accent pillows. There are two matching lamps on side tables, and a colorful woven ottoman in the center. Natural light enters through the nearby window, illuminating the space.

Apartment in New Lebanon

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.

A comfortable living area displays a vintage sofa adorned with colorful patterns, accompanied by two side tables and a floor lamp. Large windows allow natural light to enter, providing views of the outside greenery. A round rug adds warmth to the wooden floor.

4.91 out of 5 average rating, 201 reviews

Sunny Suite with Mountain Views, Steps from MoCA

Comfortable with sweeping views of the Mohawk Trail and Valley below. Two blocks, up a hill from MoCA. We are on the approach to the Mt. Greylock summit overlooking North Adams and the MohawkTrail. Within easy walking distance of Mass MoCA on a quiet street. Equal parts quirky and serene. Large, screened in porch. Nothing conventional, unique vintage decor, original art. Video doorbells provide security on all exterior entrances.

Apartment in Williamstown

A welcoming living area is featured, showcasing a comfortable blue sofa adorned with decorative pillows. A wooden coffee table sits in front, while a TV stands on a black console. Light streams through the large windows, enhanced by sheer curtains.

5 out of 5 average rating, 124 reviews

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.

A comfortable living area is presented with a gray sofa adorned with patterned throw pillows. A wooden coffee table occupies the center, accompanied by two nightstands with lamps. Natural light filters through a large window, framed by dark curtains, while a mirror adds depth to the space.

4.92 out of 5 average rating, 101 reviews

Frankie’s Place - A Mass MoCA Neighborhood 2BR APT

Experience North Adams with unbeatable convenience! This centrally located apartment puts your whole group just a short walk or bike ride away from Mass MoCA, the farmer’s market, and the shops and restaurants on Main Street. Enjoy stress-free access to all the local attractions—no parking hassles, just easy, enjoyable days exploring the best of North Adams. Perfect for your next Mass MoCA event or weekend getaway!

Superhost

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

4.85 out of 5 average rating, 133 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

4.91 out of 5 average rating, 255 reviews

A television is mounted on a wooden stand featuring an electric fireplace below. The stand contains a selection of board games and decorative items, flanked by a patterned area rug. The walls are lined with warm wood paneling, enhancing the cozy ambiance.

Apartment in Pittsfield

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. 28 minutes from Jiminy peak. Close to downtown restaurants and theaters.

4.9 out of 5 average rating, 183 reviews

#7 Downtown Historic Flatiron building getaway.

Located Downtown,walking distance to MCLA, MOCA, art and culture, great views, restaurants,dining,art & shopping. You’ll love it here because of the kitchen and the coziness, walking distance to downtown. It has been totally renovated . This place is ideal for couples, solo adventurers, and business travelers. There is metered parking within walking distance.

The light-filled living room features a comfortable gray couch with decorative pillows, a vintage coffee table, and an eclectic mix of artwork on the walls. A television is positioned on a wooden stand, and diverse seating options are provided by antique chairs and a small dining table.

4.98 out of 5 average rating, 110 reviews

Charming Art Filled Apartment

Charming and quirky, this 2nd floor apartment in a 120 year old house is decorated with art and antiques, like the living museum of an eccentric friend. Or a mini theme park for the mind. We are just blocks from downtown North Adams, on the main road into town. It’s literally a 2 minute drive to MASS MOCA, or a ten minute walk. Dogs are always welcome!