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Apartment holiday rentals in Pittsfield

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Quick stats about apartment rentals in Pittsfield

  • Total holiday rentals

    Explore 70 holiday rentals in Pittsfield

  • Nightly prices starting at

    Pittsfield holiday rentals start at $17 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,190 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Pittsfield holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Pittsfield rentals

  • 4.8 Average rating

    Pittsfield stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated apartment rentals in Pittsfield

Guests agree: These apartments are highly rated for location, cleanliness and more.

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Top Guest favourite
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

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.

FamilyLocationSleep quality

4.93 out of 5 average rating, 116 reviews
Top Guest favourite
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.
Apartment in Great Barrington

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.

FamilyLocationAir conditioning

5.0 out of 5 average rating, 148 reviews
Guest favourite
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.

LocationFamilyAccuracy

4.92 out of 5 average rating, 102 reviews
Top Guest favourite
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

LocationValueLayout

4.96 out of 5 average rating, 124 reviews
Guest favourite
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

Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.

LocationValueKitchen

4.94 out of 5 average rating, 192 reviews
Guest favourite
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.
Apartment in Great Barrington

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

LocationFamilyBathroom

4.92 out of 5 average rating, 218 reviews
Top Guest favourite
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.

ValueLocationAccess

4.9 out of 5 average rating, 232 reviews
Top Guest favourite
Apartment in North Adams

See MoCA from your mansion+Sauna!

Large bi-level 4 bedroom apartment tucked away on a hilltop oasis above Mass MoCA (3 mins by foot). 10 mins drive to Williams College & Clark. Whimsically restored (fast Wi-Fi & great water pressure). Fully private with no shared spaces + outdoor Sauna! Your stay’s proceeds allow us to host refugee/immigrant musicians pro bono year-round at @chasehillartistretreat Note: more dates are often available beyond what the calendar shows. Please don’t hesitate to inquire!

FamilyLocationBathroom

4.97 out of 5 average rating, 728 reviews
Top Guest favourite
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.

FamilyLocationOutdoor spaces

4.92 out of 5 average rating, 328 reviews
Guest favourite
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.

FamilyLocationParks

4.95 out of 5 average rating, 152 reviews
Guest favourite
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.

LocationFamilyWalkability

4.97 out of 5 average rating, 116 reviews
Top Guest favourite
A spacious front porch is framed by white columns and features two seating areas. Lush greenery encompasses the porch, with a flowering rhododendron bush in the foreground. The blue sky is dotted with clouds, enhancing the inviting atmosphere of the outdoor space.
Apartment in New Lebanon

Airy apartment at the old boarding house

Distinctive 2-bedroom with lots of windows and light and a kind of shabby elegance. It's half of a Greek Revival house from 1900 on a country lane at the foot of the Berkshires. Enormous master bedroom with dressing room, 2nd bedroom with twin beds, lovely living room, separate dining room, full kitchen. Big covered front porch for eating outside, with grill, table and an acre of orchard outside too.

FamilyLocationBathroom

4.97 out of 5 average rating, 122 reviews

Popular amenities for Pittsfield apartment rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly apartment rentals

Top Guest favourite
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.

LocationFamilyView

4.96 out of 5 average rating, 105 reviews
Guest favourite
A spacious green yard is surrounded by trees, featuring blooming vegetation. A gravel patio is visible to one side, equipped with outdoor seating and a grill. In the background, a distant view of mountains can be seen beyond the residential structures.
Apartment in North Adams

Whiteley Hideaway- walk to Mass MoCA and Downtown

LocationFamilyKitchen

4.99 out of 5 average rating, 154 reviews
Top Guest favourite
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.
Apartment in Great Barrington

Private En Suite in Beautiful Victorian

ValueLocationBackyard

4.95 out of 5 average rating, 426 reviews
Guest favourite
The living area features warm wooden floors and a cozy seating arrangement, including a sofa and an armchair. Light pours through the window, illuminating a colorful area rug and a coffee table adorned with books. A pair of opened doors leads to the spacious bedroom, showcasing a bed with decorative bedding.
Apartment in North Adams

Private guest apartment. One block from downtown.

LocationValueBackyard

4.91 out of 5 average rating, 510 reviews
Top Guest favourite
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

LocationFamilyCheckout

4.96 out of 5 average rating, 223 reviews
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

ValueFamilySkiing

4.89 out of 5 average rating, 371 reviews
Guest favourite
A comfortable living area features a sectional sofa and a single armchair arranged around a small metallic coffee table. A colorful area rug adds warmth to the space, while a lamp provides soft lighting. Exposed wooden beams enhance the architectural detail, and a door leads to the hallway.
Apartment in Williamstown

Cold Spring - The White Door

LocationFamilyParking

4.94 out of 5 average rating, 366 reviews
Guest favourite
A vintage tractor is parked on a gravel driveway, surrounded by patches of greenery. In the background, a historic white house with a front porch is visible, framed by tall trees that are bare of leaves, typical of early spring.
Apartment in Pownal

"The Parlors"

ValueLocationOutdoor spaces

4.95 out of 5 average rating, 149 reviews

Private apartment rentals

Top Guest favourite
An inviting living area is showcased, featuring exposed wooden beams and a brick fireplace. Cozy seating options include a red armchair and patterned rug. A wooden table complements the space, while shelves hold books and decorative items. A bar area is also visible in the background.
Apartment in Ashfield

Zachariah House Main St. Ashfield

ValueFamilyLayout

4.88 out of 5 average rating, 295 reviews
Top Guest favourite
Apartment in Williamstown

Downtown River Retreat, Walk to Shops and College

ValueFamilyDecor

4.96 out of 5 average rating, 336 reviews
Top Guest favourite
A wide expanse of green grass is framed by a line of trees under a blue sky dotted with fluffy white clouds. The landscape conveys a sense of open space and tranquility, characteristic of the surrounding rural setting.
Apartment in Plainfield

Sunny carriage house apartment

LocationFamilyQuiet

4.95 out of 5 average rating, 303 reviews
Guest favourite
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.
Apartment in Pittsfield

Spacious 2 bedroom downtown very nice area!

LocationFamilyParking

4.79 out of 5 average rating, 58 reviews
Top Guest favourite
A spacious living area features a sectional sofa in muted green, paired with a brown leather recliner. Natural light fills the room through large windows, and a painting adds a touch of color to the light walls. A circular table is situated in front, with a textured area rug underfoot.
Apartment in Pittsfield

Modern Gem in the Heart of Berkshires

LocationFamilyNearby

4.94 out of 5 average rating, 71 reviews
Guest favourite
A two-story house features a welcoming front porch with white railings and multiple planters. Red shutters adorn the windows, complementing the light-colored siding. A well-maintained lawn stretches in front, bordered by a path leading to the entrance. The setting reflects a pleasant neighborhood atmosphere.
Apartment in Dalton

1843 House - Bright and Airy 5 Rooms (2 Bedrooms)

FamilyValueComfort

4.9 out of 5 average rating, 21 reviews
Guest favourite
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

LocationValueCheckout

4.87 out of 5 average rating, 82 reviews
Top Guest favourite
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.
Apartment in Great Barrington

The River’s Whisper

LocationFamilyDecor

4.98 out of 5 average rating, 48 reviews

Apartment rentals with a hot tub

Guest favourite
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

LocationValueLong stay

4.91 out of 5 average rating, 208 reviews
Guest favourite
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.
Apartment in Hancock

Ski-InSki-Out Loft Lift&MT.Views

LocationFamilyDecor

4.95 out of 5 average rating, 55 reviews
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.
Apartment in Hancock

Mountainside Condo Ski on/off

LocationFamilyAmenities

4.84 out of 5 average rating, 44 reviews
Guest favourite
Apartment in Troy

Luxury Downt. Troy Apartments near Franklin Plaza.

FamilyLocationKitchen

4.88 out of 5 average rating, 8 reviews
Superhost
Apartment in Hancock

Ski-In Jiminy Peak 2 Bed/2 bath Condo

AmenitiesPoolComfort

Guest favourite
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)

LocationFamilyNearby

4.87 out of 5 average rating, 179 reviews
Guest favourite
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.
Apartment in Hancock

Gorgeous Zen Must-See Suite At Jiminy Country Inn

ValueFamilyIndoor spaces

4.92 out of 5 average rating, 37 reviewsA red front door, framed by a small overhang, is adorned with hanging flowers. Colorful blooms, including yellow marigolds and pink flowers, surround the entrance, creating a welcoming atmosphere. Sunlight casts gentle shadows on the stone pathway leading to the door.
Apartment in North Adams

The Crystal Loft

LocationValueWi-Fi

4.7 out of 5 average rating, 121 reviews

When is the best time to visit Pittsfield?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$126 NZD$115 NZD$126 NZD$127 NZD$161 NZD$210 NZD$161 NZD$161 NZD$144 NZD$158 NZD$131 NZD$131 NZD
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°C-2°C

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