Apartment holiday rentals in Pittsfield

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.

4.93 out of 5 average rating, 110 reviews

Downtown Apartment A

Centrally located in the Berkshires. Enjoy a beautiful day at Tanglewood, view the amazing art at Mass Moca or discover nature on one of the many hiking/biking trails the Berkshires has to offer. Located 5 mins from Bousquet and close to Jimmy Peak as well for anyone enjoying the snow! There are a variety of delicious restaurants to suit any appetite. Located in a quiet neighborhood, if your out & about all day or just looking to get away from the hustle & bustle of the city it's a perfect spot.

LocationFamilyOutdoor spaces

A three-story house features a welcoming front porch with multiple steps leading to the entrance. The exterior is painted in light tones, complemented by a well-maintained lawn and flower beds. A paved driveway is visible, along with nearby trees providing shade.

4.94 out of 5 average rating, 175 reviews

Heart Of The Berkshires

A newly renovated apartment with all of the comforts of home. Fully stocked kitchen, including spices. Modern major appliances, inc. garbage disp. and dish washer. New pots and pans, dishes and silverware. Three bedrooms all with allergy free mattress and pillow covers. Plenty of towels.! We're centrally located in a nice, safe neighborhood. We're close to Tanglewood, Berkshire Theatre, The Colonial Theatre, Barrington Stage, Berkshire Museum and Jiminy Peak. Plenty of off street parking.

FamilyValueTV

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

FamilyValueCheck-in

Apartment in Great Barrington

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, 213 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

LocationValueShared spaces

4.9 out of 5 average rating, 229 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

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.

ValueLocationQuiet

4.96 out of 5 average rating, 218 reviews

A spacious, two-story dark wooden building is nestled among trees, showcasing a welcoming entrance with a large front porch. Lush green grass surrounds the structure, enhancing its serene setting. Bright blue skies and scattered clouds further complement the inviting atmosphere.

Apartment in Conway

A Country Retreat-Enhanced Studio Apartment

Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, having hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

LocationFamilyView

4.99 out of 5 average rating, 264 reviews

A living room is displayed, featuring a comfortable blue couch adorned with patterned pillows. Three framed landscape images are mounted on the wall above a wooden coffee table. Natural light enters through a window with sheer curtains, illuminating a cozy reading nook in the background.

Apartment in Northampton

Cozy Haven: Convenience & Charm

Welcome to our charming Florence, Massachusetts Airbnb! Only 10 minutes from downtown Northampton, our newly renovated property blends comfort, convenience, and natural beauty. Our location provides swift access to Northampton's vibrant heart. Within a 10-minute drive, you'll be amid bustling streets with eclectic shops, superb dining, and a lively arts scene. Explore boutiques, galleries, and cafes that define Northampton's creative and entertaining spirit.

FamilyLocationGetting around

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.

4.92 out of 5 average rating, 324 reviews

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.

LocationValueHiking

4.95 out of 5 average rating, 149 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.

FamilyLocationCleanliness

4.97 out of 5 average rating, 114 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.

LocationFamilyNearby

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.

4.98 out of 5 average rating, 257 reviews

Serene Suite: Hudson & Berkshires, Walk to Brewery

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.

FamilyLocationCheck-in

4.96 out of 5 average rating, 724 reviews

The charming exterior of a Victorian home is framed by vibrant autumn foliage. A welcoming porch extends across the front, featuring a red door and large windows that create a bright atmosphere. The roof is adorned with traditional shingles, contributing to its historic character.

Apartment in North Adams

Steps to MoCA: 2bd + SAUNA!

A large, private 2-bedroom apt at the Small Mansion of Chase Hill Estate. Outdoor Sauna! Just a 5 minute-walk to MASS MoCA & downtown restaurants, 10 mins drive to Williams College & Clark. Whimsically restored (fast Wi-Fi & great water pressure!) and part of @chasehillartistretreat ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!

FamilyValueParks

Popular amenities for Pittsfield apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.99 out of 5 average rating, 196 reviews

A modern kitchen features a central island with bar stools, stainless steel appliances, and white cabinetry. Natural light floods the space through a skylight and large windows, highlighting the open layout. A dining area with dark chairs sits adjacent to the kitchen.

Apartment in Charlemont

Suite 23 - Spacious Sunny 2-BR with Mountain view

FamilyLocationGetting around

Apartment in Great Barrington

The exterior view of a spacious two-story home is presented, featuring a wraparound porch supported by white columns. Large windows illuminate the façade, while vibrant greenery from surrounding trees and gardens enhances the tranquil atmosphere.

4.95 out of 5 average rating, 421 reviews

Private En Suite in Beautiful Victorian

FamilyValueAir conditioning

4.97 out of 5 average rating, 305 reviews

A bright living area is highlighted by a slanted ceiling and a pellet stove, offering warmth and comfort. Two black chairs are positioned on a patterned rug, while a sectional sofa provides spacious seating. Natural light filters through a skylight and window adorned with light curtains.

Apartment in Plainfield

Sunny, light filled loft in 1873 Colonial

LocationValueLong stay

Superhost

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

4.9 out of 5 average rating, 317 reviews

Catskill Village House - Mountain View Studio

LocationValueAccuracy

Apartment in Williamstown

A comfortable living area features a light gray sectional sofa and an accent chair, accompanied by a sleek coffee table. Large windows allow natural light to fill the space, which is complemented by a textured area rug and a modern floor lamp.

4.98 out of 5 average rating, 148 reviews

House on the Town Green

LocationFamilyAccess

Apartment in Williamstown

4.94 out of 5 average rating, 133 reviews

Charming Farmhouse Apt Near Williams College

LocationValueCondition

4.9 out of 5 average rating, 274 reviews

Apartment in Albany

Historic, Spacious Mansion Suite

LocationFamilyBreakfast

4.96 out of 5 average rating, 114 reviews

Apartment in Bennington

Suite Sunset 311 Rice Lane Bennington VT

LocationValueDecor

Private apartment rentals

5.0 out of 5 average rating, 151 reviews

A warm living area showcases a comfortable sofa with soft upholstery. A decorative tray holds a candle on a rustic coffee table. In the background, glass doors open to a scenic view of the outdoors, framed by a dining table with a vase of fresh flowers.

Apartment in Lee

Lovely Berkshire Apartment. Private & Peaceful

ValueFamilyLaundry

4.96 out of 5 average rating, 103 reviews

The exterior of a two-story purple house is featured, showcasing a wrap-around porch with white rocking chairs and a small table. Large windows allow ample natural light, while a green planter hangs near the entrance, surrounded by lush foliage.

Apartment in North Adams

"Nostalgia" a spacious2 bedroom first floor unit.

LocationFamilyComfort

Apartment in Shelburne Falls

A bright living space features large windows, allowing natural light to fill the room. A comfortable sofa sits beside a wooden coffee table, with visible mountain views outside. A round dining table is surrounded by wooden chairs, enhancing the room's spacious feel.

4.92 out of 5 average rating, 321 reviews

Sunny, soaring 2-level downtown loft, scenic views

LocationFamilyBiking

A rustic bar area features a long wooden counter with five leather-upholstered stools positioned along one side. An antique clock and decorative items add character to the shelves above. Warm wood tones create an inviting ambiance, reflecting the unit's historic charm.

5.0 out of 5 average rating, 72 reviews

Comfy Quaint Tavern

FamilyValueHiking

A white arbor is framed by vibrant yellow and orange flowers, leading towards a two-story home. The building features a classic design with a central entrance. Lush greenery surrounds the area, under a partly cloudy sky that highlights the outdoor setting.

4.79 out of 5 average rating, 58 reviews

Spacious 2 bedroom downtown very nice area!

LocationFamilyAccess

4.88 out of 5 average rating, 80 reviews

A comfortable sleeping area is highlighted by a queen-size bed, adorned with gray patterned bedding and neatly arranged towels. Two nightstands, each with a lamp, flank the bed, while a wooden chair offers additional seating. A closet provides storage space, and art decorates the wall.

Apartment in Adams

Downtown Studio in Adams

ValueLocationBathroom

4.97 out of 5 average rating, 31 reviews

Apartment in Lee

Eliza Suite

LocationNearbyParking

5.0 out of 5 average rating, 32 reviews

A spacious living area is furnished with a large leather couch and a comfortable sofa with decorative cushions. A wooden coffee table sits centrally, while a flat-screen television is mounted on an adjacent wall. Two large windows allow natural light to fill the room.

Apartment in New Lebanon

Loft Space above Brewery

FamilyValueSkiing

Apartment rentals with a hot tub

4.94 out of 5 average rating, 188 reviews

A spacious mountain lodge is depicted, featuring a striking stone chimney and expansive decks. Large windows frame the scenic landscape, while lush green grass surrounds the building. The warm tones of the log exterior harmonize with the natural setting, inviting outdoor relaxation.

Apartment in North Adams

Berkshire Mountain Top Chalet

FamilyLocationCondition

4.91 out of 5 average rating, 203 reviews

A living area features brown leather sofas arranged for relaxation. A decorative mirror hangs on the tan wall, reflecting the space. A flat-screen TV sits on a stand beside a soft area rug, while an open archway reveals the dining area, inviting light from nearby windows.

Apartment in Troy

Troy-Timeless Rensselaer Victorian

FamilyLocationLong stay

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-In Ski-Out Loft Lift & MT. Views

LocationValueGetting around

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

FamilyLocationIndoor spaces

4.86 out of 5 average rating, 7 reviews

Apartment in Troy

Luxury Downt. Troy Apartments near Franklin Plaza.

FamilyLocationBarbecue

Superhost

Ski-In Jiminy Peak 2 Bed/2 bath Condo

PoolDecorSleep quality

4.87 out of 5 average rating, 178 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)

ValueLocationComfort