Apartment holiday rentals in Great Barrington

A cozy living room features a light sofa and two armchairs flanking a wooden coffee table. A decorative rug with intricate patterns lies beneath. Natural light filters through multiple bay windows, highlighting the serene and vintage-inspired decor.

5.0 out of 5 average rating, 148 reviews

Walk Everywhere! | Relax in Easy Elegance!

Gracious in-town apartment feels like home: living and dining rooms, kitchen, 2 bedrooms, 2 baths—all just for you and your group. Walk to shops, restaurants, theaters, farmers’ market. Drive to more nearby arts offerings, hiking, skiing, swimming. Spectrum WiFi; please note, there is no TV. Bedrooms are small but with plenty of space to spread out, relax, read, play games or enjoy a meal in the entire apartment. The shared porch is available for morning coffee, evening cocktails or a good book.

FamilyLocationSkiing

4.92 out of 5 average rating, 103 reviews

A modern kitchen features clean lines and natural light. The space includes a refrigerator, stove, and a dining table with two chairs. Soft white cabinetry is complemented by a wooden tabletop, while a window offers views of the outdoors, enhancing the open and airy feel.

Apartment in Stockbridge

Stockbridge private apartment

Newly renovated apartment, just one mile from Downtown Stockbridge. This cozy apartment offers gorgeous mountain views and access to the lush backyard area. 10 minutes from local attractions such as Tanglewood, the Stockbridge bowl, and Kripalu. Close to many hiking trails, including backyard access to a riverside walking trail This apartment is attached to the owners house, however it has a private entrance and is completely separate. The parking area is shared- there is space for two cars.

LocationFamilyLaundry

4.96 out of 5 average rating, 124 reviews

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

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

LocationValueCondition

5.0 out of 5 average rating, 415 reviews

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

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.

FamilyLocationOutdoor spaces

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.

4.92 out of 5 average rating, 220 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

ValueFamilyPets

4.99 out of 5 average rating, 182 reviews

The exterior of a two-story house is displayed, featuring a combination of white siding and a metal roof. An American flag hangs from the porch, surrounded by greenery and flower beds. The front pathway leads to a welcoming porch space.

Apartment in Canaan

West Main

1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town , pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

LocationFamilyGetting around

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.

4.89 out of 5 average rating, 371 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! Note: there is no TV.

FamilyValueGetting around

4.92 out of 5 average rating, 329 reviews

A cozy living room is furnished with two comfortable sofas and a coffee table set on a patterned rug. Natural light enters through a window, illuminating wall art and decorative elements. A door leads to a balcony area, enhancing the space's inviting feel.

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. 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.

FamilyLocationBathroom

4.95 out of 5 average rating, 153 reviews

The bedroom features a spacious bed with a light grey coverlet, accentuated by decorative pillows. Natural light filters through two windows adorned with bamboo shades. A light-colored dresser and a cozy armchair add functionality, complemented by a soft area rug on the hardwood floor.

Apartment in Lenox

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.

FamilyLocationKitchen

4.97 out of 5 average rating, 117 reviews

A light and neutral living room showcases a comfortable sectional sofa with decorative pillows. A round marble coffee table is positioned in front, adorned with a small plant. Two framed art pieces hang above the sofa, and textured rugs lie across the wooden flooring.

Apartment in Lenox

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.

LocationFamilyComfort

4.91 out of 5 average rating, 179 reviews

A welcoming living area is highlighted by natural light streaming in through large windows. A comfortable sectional sofa is paired with two patterned chairs and a round woven coffee table, creating an inviting space for relaxation. A television is positioned on an elegant media console.

Apartment in Craryville

Captain's Quarters at Mickey's Marina

The Captain's Quarters is a one-of-a-kind rental experience at Copake Lake. Our 3-bedroom, 2-bathroom apartment features high ceilings and spacious living areas with a fresh take on the lake house aesthetic. Enjoy our open kitchen, living and dining area thoughtfully appointed with an island bar, large table and comfortable seating area. In the morning, sip your coffee or tea out on the front porch as you take in the lakeside views!

ValueFamilyKitchen

4.96 out of 5 average rating, 140 reviews

The exterior of the vintage duplex is highlighted by blue siding and white trim, featuring a welcoming porch adorned with colorful decorations. A spacious lawn surrounds the property, complemented by shrubs and greenery, providing a peaceful outdoor setting.

Apartment in New Lebanon

Sunny Duplex at the old boarding house

Charming big vintage apartment 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. Note that the attic bedroom gets closed in the wintertime. Small front sitting porch, big side lawn and flowery backyard with grill and table.

ValueLocationBarbecue

Popular amenities for Great Barrington apartment rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

An outdoor patio area features a stone surface surrounded by colorful flower beds. A round table with chairs and a large umbrella provide seating, alongside a charcoal grill. The home's entrance is highlighted by a welcoming red door and large windows.

4.93 out of 5 average rating, 211 reviews

Secluded but not isolated Berkshire Retreat

FamilyValueKitchen

Apartment in East Chatham

A tranquil sleeping area features a wooden bed topped with a vibrant patterned quilt. Natural light enters through a window, illuminating the space. A wooden cabinet and a side table with a lamp add functionality, complemented by artwork on the walls showcasing nature scenes.

4.96 out of 5 average rating, 191 reviews

Bennett Abode

LocationFamilyDecor

4.95 out of 5 average rating, 381 reviews

A bright living area features a comfortable sofa adorned with decorative pillows in relaxing tones. A vibrant yellow armchair adds a pop of color, while natural light fills the space through large windows with soft curtains. A round coffee table sits at the center, accompanied by a sleek TV stand.

Apartment in Hudson

Stylish Hudson Getaway

FamilyLocationTV

4.93 out of 5 average rating, 116 reviews

A modern kitchen is displayed, featuring an arrangement of appliances including a stove, microwave, and refrigerator. A dining table sits in the center, complemented by a green patterned rug. Sunlight filters through a nearby door, illuminating the open layout and inviting atmosphere.

Apartment in Pittsfield

Downtown Apartment A

LocationFamilyBreakfast

4.97 out of 5 average rating, 204 reviews

A friendly horse leans through an open window, with soft curtains framing its gentle face. The horse's striking black and white markings are visible, while light filters softly into the room, highlighting the welcoming ambiance.

Apartment in Coxsackie

Susie's Climax Creations

LocationValueHeating

4.96 out of 5 average rating, 133 reviews

A lush, green lawn gently slopes toward a small pond, framed by trees on either side. The natural foliage provides shade and privacy, while a stone is visible among the undergrowth. The area is serene, inviting reflection and connection with nature.

Apartment in Otis

Enjoy every season the Berkshires have to offer.

LocationValueBackyard

4.99 out of 5 average rating, 167 reviews

A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.

Apartment in Coxsackie

Hudson River Beach House

ValueLocationWi-Fi

4.9 out of 5 average rating, 323 reviews

A spacious living area is illuminated by natural light from large windows. A comfortable sofa is positioned beside a wooden coffee table. A raised dining area is visible, furnished with two chairs and a small table. The kitchenette features open shelving and rustic accents.

Apartment in Catskill

Catskill Village House - Mountain View Studio

FamilyValueLayout

Private apartment rentals

4.9 out of 5 average rating, 232 reviews

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 Petersburg

The Beer Diviner Brewery Apartment

FamilyLocationLayout

4.84 out of 5 average rating, 146 reviews

Apartment in Millerton

The Studio

LocationFamilyHeating

4.9 out of 5 average rating, 176 reviews

A cozy studio space features a full-size bed with a neutral comforter, a desk and chair set against a wall, and a small television mounted above a radiator. Natural light enters through a window, with patterned curtains framing the view. The bathroom doorway is visible in the background.

Apartment in Amenia

Amenia Main St Cozy Studio

FamilyLocationBackyard

4.94 out of 5 average rating, 461 reviews

A bright dining area features a wooden table centered under a woven pendant light, surrounded by white chairs. A fresh floral centerpiece accompanies a bowl of fruit. Doorways to adjacent rooms are visible, enhancing the open layout and inviting atmosphere.

Apartment in Hudson

Light Filled 2+BR in the Heart of Hudson

LocationFamilyParking

A charming red house is framed by green trees and colorful plants in front. The home features a welcoming porch adorned with vibrant flowers, creating a harmonious blend with the surrounding natural landscape.

4.98 out of 5 average rating, 48 reviews

The River’s Whisper

LocationFamilyQuiet

A bright sunroom features large windows that allow natural light to illuminate the space. A gray and white patterned rug lies on the floor, complementing a cozy seating area with yellow cushions. A green dining table with chairs and potted plants add a touch of color.

4.93 out of 5 average rating, 43 reviews

Zen River Studio

LocationValueHot tub

A bottle of pale ale stands on a glass table, accompanied by a glass of beer and a small bowl. In the background, the Housatonic Water Tower is visible, framed by greenery and rolling hills under a partly cloudy sky.

5.0 out of 5 average rating, 39 reviews

Cozy, Quiet Apt. in Housatonic, Great Barrington

ValueFamilyHospitality

4.98 out of 5 average rating, 54 reviews

A serene outdoor area features two lounge chairs beneath a striped umbrella, situated on a verdant lawn. Nearby, a portable fire pit is surrounded by chairs, with a red kayak positioned along the riverbank, offering a relaxing view of the water and surrounding trees.

Apartment in Stockbridge

Three bedroom duplex in Stockbridge on the river

FamilyLocationPets

Apartment rentals with a hot tub

5.0 out of 5 average rating, 124 reviews

The kitchen showcases wooden cabinetry and a central island with two bar stools. A black refrigerator and stainless steel stove are visible. Natural light filters through a window, illuminating the warm wooden flooring and countertops.

Apartment in Catskill

Little Farm Stay Catskill

ValueFamilyIndoor spaces

A view from the condo showcases snow-covered slopes leading up to the mountain, with ski lifts operating in the distance. The landscape is framed by the rustic stone chimney of the adjacent building, creating a serene winter scene.

4.95 out of 5 average rating, 55 reviews

Ski-InSki-Out Loft Lift&MT.Views

ValueFamilyPool

An outdoor pool area is surrounded by several lounge chairs and umbrellas, offering a view of vibrant autumn foliage on the hills. The pool is partially covered, and a building is visible in the background, enhancing the resort-like atmosphere.

4.84 out of 5 average rating, 44 reviews

Mountainside Condo Ski on/off

FamilyValueAccess

4.95 out of 5 average rating, 37 reviews

An outdoor deck features a hot tub surrounded by wooden flooring. Comfortable seating arrangements include a sectional couch and lounge chairs adorned with blue and white pillows. A large umbrella provides shade, while a clock and decorative elements add to the inviting space.

Apartment in Ravena

Mountain Getaway Studio apt

ValueLocationDecor

5.0 out of 5 average rating, 6 reviews

Apartment in Saugerties

Charming Creekfront | Sauna• Hot Tub • Fire Pit

LocationFamilyKitchen

Ski-In Jiminy Peak 2 Bed/2 bath Condo

ParkingSkiingGetting around

4.87 out of 5 average rating, 180 reviews

The log home is framed by lush greenery, with a rainbow arching over the hillside in the background. Solar panels are visible on the roof, and a small, illuminated outdoor lamp stands in the foreground, providing a welcoming touch to the natural setting.

Apartment in Hawley

Green Acres Hawley Upper Studio (Bonus Room)

LocationValueQuiet

A bright living area features a soft gray sofa with decorative pillows, complemented by a plush area rug. A coffee table holds decorative items, and a seating area includes a cozy recliner. Large windows allow ample natural light while providing views of the outdoors.