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, 149 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.

ValueFamilyParking

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.

FamilyLocationOutdoor spaces

A modern bedroom showcases a spacious bed with crisp white linens. Accent lighting frames the walls, and a patterned area rug adds warmth to the space. A compact seating area with stylish benches complements the décor, while an entrance leads to a private bathroom.

4.91 out of 5 average rating, 178 reviews

King Bed | Stylish | 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

ValueFamilyQuiet

4.96 out of 5 average rating, 125 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

ValueLocationKitchen

5.0 out of 5 average rating, 416 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.

LocationFamilyAccuracy

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.

FamilyLocationLaundry

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

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. .

FamilyLocationPets

Superhost

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

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.

FamilyLocationCheck-in

4.89 out of 5 average rating, 373 reviews

Apartment in Town of Hillsdale

A spacious bedroom features a wooden four-poster bed adorned with green and white pillows. A dining table with two chairs sits in one corner. Soft lighting is provided by a lamp and two hanging chandeliers, creating a calm ambiance.

Serene Suite: Hudson & Berkshires, Walk to Brewery

No cleaning fee and no chores! A peaceful, highly rated private suite in the heart of historic Hillsdale, where the Hudson Valley meets the Berkshires. Walk to shops, restaurants, a brewery, cooking school, grocery, wine and liquor store. Minutes to Hilltown, the Harlem Valley Rail Trail, scenic hikes, and beautiful drives, with galleries, antiques, live music, and cultural gems nearby. A serene, perfectly located home base for spring dining, exploring, and unwinding.

FamilyLocationWalkability

4.98 out of 5 average rating, 263 reviews

4.95 out of 5 average rating, 154 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.

LocationFamilySleep quality

4.96 out of 5 average rating, 118 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.

FamilyLocationAccuracy

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!

LocationFamilyNearby

Popular amenities for Great Barrington apartment rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.92 out of 5 average rating, 330 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

ValueLocationNearby

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.

Bennett Abode

LocationValueAmenities

4.96 out of 5 average rating, 191 reviews

4.93 out of 5 average rating, 117 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

LocationFamilyQuiet

4.97 out of 5 average rating, 205 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

FamilyLocationKitchen

4.96 out of 5 average rating, 134 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.

FamilyValueOutdoor spaces

4.95 out of 5 average rating, 382 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

FamilyLocationSleep quality

4.99 out of 5 average rating, 168 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

LocationValueTV

4.9 out of 5 average rating, 235 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

LocationFamilyGetting around

Private apartment rentals

4.84 out of 5 average rating, 147 reviews

Apartment in Millerton

The Studio

LocationValueLong stay

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

FamilyLocationKitchen

4.99 out of 5 average rating, 159 reviews

Apartment in Torrington

“The Clemons!” Central AC - 3 Beds - Main Level

LocationFamilyHiking

4.91 out of 5 average rating, 179 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

ValueLocationHiking

4.91 out of 5 average rating, 422 reviews

A bright and inviting living room features a floral-patterned couch and large windows adorned with green curtains. Decorative plant stands filled with various plants enhance the space, while a stained glass light fixture casts a warm glow over the area. A cozy atmosphere is created with soft lighting.

Apartment in Winchester

Gateway to the Berkshires

FamilyLocationParking

4.96 out of 5 average rating, 287 reviews

The kitchen features modern white cabinetry with black handles, complemented by a light-colored countertop. A stainless steel sink is positioned under a wall-mounted faucet. A tile backsplash in neutral tones adds texture, while a fire extinguisher is mounted for safety.

Apartment in Pine Plains

Newly renovated cutie

LocationFamilyTV

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, 51 reviews

The River’s Whisper

FamilyLocationGetting around

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

LocationValueGetting around

Apartment rentals with a hot tub

5.0 out of 5 average rating, 126 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

ValueFamilyBathroom

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

ValueLocationComfort

Superhost

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

LocationValueHot tub

5.0 out of 5 average rating, 6 reviews

Apartment in Saugerties

Charming Creekfront | Sauna• Hot Tub • Fire Pit

LocationFamilyComfort

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

ValueLocationOutdoor spaces

Superhost

Ski-In Jiminy Peak 2 Bed/2 bath Condo

Sleep qualityPoolAmenities

4.87 out of 5 average rating, 181 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)

ValueLocationSkiing

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.