Apartment vacation rentals in Pittsfield

Apartment in Shelburne Falls

The bright studio features a cozy sleeping area with a spacious bed, a comfortable yellow armchair, and two plush couches. A coffee table sits in the center, with large windows allowing natural light and views of greenery. A television is mounted on the wall.

4.97 out of 5 average rating, 594 reviews

In town, newly renovated studio with private deck

Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

Apartment in Lanesborough

A wooden sign with a circular cutout features the name 'Second Drop Farm' prominently displayed in metallic letters. Inside the circle, a metal silhouette of a tree is depicted, showcasing intricate branches and roots against a rustic wooden background.

4.9 out of 5 average rating, 138 reviews

Cozy Rustic Apt. in 18th c. Berkshire Farmhouse

This cozy rustic studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in the 1700’s, this centuries old farmhouse has since been converted into four separate cute suites. Newly updated kitchen, bathroom and furniture. Enjoy exploring the sprawling 19 acre property you will be staying on which includes seasonal flower fields, thousands of berry bushes, fruit trees, creek, and walking trails full of wildlife. Follow us on IG @SecondDropFarm

4.89 out of 5 average rating, 203 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 Petersburgh

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.

4.97 out of 5 average rating, 285 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

Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!

4.96 out of 5 average rating, 121 reviews

The living area features a comfortable seating arrangement with a patterned armchair and a light-colored sofa accented by a vibrant throw. A side table is positioned next to the sofa, and a wall clock adds a decorative touch, while wooden flooring enhances the cozy ambiance.

Apartment in Troy

Adorable Apartment - Near Emma Willard, RPI, Troy

Welcome to Cheri's house! You'll enjoy a private 1 bedroom apartment including a full size bed in the bedroom, living room with pull-out sofa and smart TV, full kitchen, bathroom and bonus work space or dining room. Off street parking, free WiFi and breakfast included. My home is a quick 5 min walk to Emma Willard School, 1.5 miles to RPI, and 2 miles to Russell Sage College. The unit is on the 2nd floor of an owner-occupied house. Please ask me any questions!

4.94 out of 5 average rating, 474 reviews

An open studio layout features a sleeping area with a spacious bed and a colorful area rug. A wooden loft with stairs for access is visible in the background. Bathroom and kitchen areas are partially seen, providing convenience and functionality.

Apartment in Troy

Stunning studio in the heart of Troy: Raven's Den

Raven's Den is a large studio apartment with a queen sized bed, full kitchen, and an extra-deep bathtub. It is an open plan room that can be configured as needed, featuring two "aerial silk" hammocks that double as swings. It's in the heart of Downtown Troy, close to RPI, EMPAC, The Troy Music Hall, The Farmers Market, and the Takk House. Whether you need a cozy romantic getaway or simply a clean, fresh, place to lay your head, Raven's Den could be for you.

A large Victorian house is framed by vibrant autumn foliage, with colorful orange, yellow, and red leaves. The home features a spacious porch and multiple gabled roofs, blending harmoniously with the surrounding nature and the peaceful landscape.

4.96 out of 5 average rating, 622 reviews

Steps to MoCA: 2bd + SAUNA!

A spacious, private two-bedroom at the Small Mansion of Chase Hill Estate in North Adams. Just 3 minutes to MASS MoCA, 5 minutes to downtown restaurants, and 10 minutes to Williams College or The Clark. Closest ⛷️ SKI resorts are Jiminy Peak and Berkshire East Mountain. Whimsically restored (yes—fast Wi-Fi & great water pressure!) and part of @chasehillartistretreat. ✨ Your stay supports pro bono residencies for refugee & immigrant artists.

Apartment in Center Square

A charming entrance to the garden apartment is presented, featuring a black door flanked by windows and adorned with flower boxes. A set of black wrought-iron stairs leads to the entrance, while a flower planter with vibrant blooms adds color to the pathway.

4.94 out of 5 average rating, 191 reviews

Empire Plaza Apartment

Welcome to our garden apartment, nestled in a walkable neighborhood filled with diverse restaurants, cozy pubs, and the picturesque Washington Park. The apartment features a sound-dampened bedroom, ensuring a serene and peaceful retreat. Just steps away, you'll find the New York State Capitol, Empire State Plaza, The Egg, and the New York State Museum, making this location ideal for both relaxation and exploration.

4.96 out of 5 average rating, 114 reviews

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.

4.87 out of 5 average rating, 154 reviews

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

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

4.88 out of 5 average rating, 198 reviews

An inviting entrance area showcases a vintage Coca-Cola vending machine. A wooden door leads into a room with a detailed patterned wallpaper. A decorative stove stands prominently, complementing the warm aesthetic of the space.

Apartment in Lenox

Station House 1E Private Room & Bath

Our place is a central location in Berkshire County, short drive to restaurants and shops; art and culture, skiing and hiking also close by. You’ll love this former train station( next to the Housatonic RR tracks) which is on three acres between a chapel, the scenic Housatonic River and October Mountain. Our place is good for couples, solo adventurers, and business travelers.

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, 289 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. 28 minutes from Jiminy peak. Close to downtown restaurants and theaters.

Popular amenities for Pittsfield apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

Apartment in Center Square

4.93 out of 5 average rating, 205 reviews

Historic, Spacious Mansion Suite

4.98 out of 5 average rating, 266 reviews

The living room features a light-colored sofa adorned with assorted pillows, positioned next to large windows that invite natural light. A vibrant area rug adds warmth to the wooden floor. Decorative plants and a framed piece of art contribute to the inviting atmosphere.

Apartment in Hudson

Serving Sexy Historic Hudson Realness Steps from Warren St

The exterior of the condominium building is highlighted, featuring a two-story design with a light blue facade. Lush greenery surrounds the property, enhancing the natural setting. A gravel pathway leads to the entrance, and outdoor seating areas are visible in the landscaped garden.

4.99 out of 5 average rating, 206 reviews

Overlooking the city in a quiet 7 unit building.

A comfortable living area features a gray futon sofa and a wooden coffee table. Natural light enters through two large windows, which are equipped with shades. A compact television is positioned on a stand in the corner, complementing the modern decor.

4.92 out of 5 average rating, 51 reviews

Comfortable Pittsfield Loft

4.95 out of 5 average rating, 203 reviews

A spacious bedroom is showcased with a wooden bed frame and comfortable linens, complemented by two bedside lamps. Natural light floods the space through windows adorned with simple treatments, and a cozy rug lies beneath. A small table and a decorative plant add warmth to the inviting atmosphere.

Apartment in Valatie

Holland House: Modern Rustic Guest Apartment

A welcoming bedroom features a spacious bed with a light duvet and decorative pillows. A wooden dresser stands beside the bed, and natural light filters through a window adorned with light curtains. Soft wooden flooring enhances the room's warm ambiance.

4.92 out of 5 average rating, 131 reviews

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

4.93 out of 5 average rating, 206 reviews

A comfortable living area features a gray sofa adjacent to a wooden table and two chairs. Natural light filters through sheer curtains on the windows, highlighting the rustic wood flooring and a statement brick wall with a vintage-style light fixture above.

Apartment in Catskill

Catskill Village House - Garden Studio

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 out of 5 average rating, 57 reviews

Comfy Quaint Tavern

Private apartment rentals

Apartment in Great Barrington

A cozy living area features a spacious blue sofa, wooden dining table, and decorative rug. Large glass doors provide views of the surrounding greenery, while soft pendant lights illuminate the space. A blend of natural wood and light-colored walls creates a calming atmosphere.

4.8 out of 5 average rating, 282 reviews

Beautfiul, modern, GB apartment

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, 96 reviews

Downtown Apartment A

An open concept kitchen and living area features light-colored cabinetry and modern appliances. A spacious kitchen island with seating is positioned next to the stainless steel dishwasher and stove. Decorative elements add character to the inviting space, with natural light illuminating the area.

4.61 out of 5 average rating, 71 reviews

Beautiful Apartment in Central Pittsfield

4.95 out of 5 average rating, 62 reviews

A serene sleeping area features a spacious bed adorned with white linens and a decorative pillow displaying floral patterns. An orange lamp softly illuminates the room, contrasting with the muted gray walls. A framed piece of art adds a touch of sophistication above the bed.

Apartment in Lenox Dale

Cute, Cozy and Comfortable apartment

4.54 out of 5 average rating, 26 reviews

A spacious sleeping area features a large bed with a soft white duvet, complemented by two windows providing natural light. A modern sofa is positioned against one wall, and a small nightstand is beside the bed, creating a comfortable, inviting space.

Apartment in Adams

Guestrooms on the Bike Trail

5 out of 5 average rating, 30 reviews

A welcoming bedroom features a spacious bed dressed in white linens and accented by two bedside tables with lamps. Natural light fills the room through a large window, complemented by a decorative rug with floral patterns on the floor.

Apartment in Lenox

Center of Lenox, cozy Apartment 2-bedroom

4.97 out of 5 average rating, 72 reviews

A cozy living room is featured with natural light streaming through large windows. A comfortable sectional sofa and two stylish armchairs are arranged around a round coffee table. Decorative elements include a soft throw and an elegant light fixture hanging from the ceiling.

Apartment in Lenox

Main Street Delight - One Bedroom Apartment

5 out of 5 average rating, 383 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

Apartment rentals with a hot tub

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.

4.82 out of 5 average rating, 38 reviews

Mountainside Condo Ski on/off

A cozy living area showcases a combination of comfortable seating, including a sectional sofa with decorative pillows and a patterned armchair. A wooden table complements the space, while a mounted television is visible on the wall. Natural light enters through the window, enhancing the inviting atmosphere.

4.83 out of 5 average rating, 6 reviews

Cozy Ski Retreat

4.97 out of 5 average rating, 33 reviews

A comfortable living space features a warm-toned sofa, wooden tables, and a dining area with a large table and six chairs. Natural light filters through the window adorned with dark curtains, creating a bright and inviting atmosphere.

Apartment in Dover

Mt Snow 2 Bdrm Condo - Free Ski Shuttle

A cozy living area features a tall Christmas tree adorned with lights and ornaments next to a glass-top coffee table. A fireplace with built-in decor sits beneath a mounted television. Velvety blue chairs complement an orange accent pillow on the nearby couch, surrounded by large windows with sheer curtains.

4.78 out of 5 average rating, 18 reviews

Artsy Ski Loft with Hot Tub near MassMoca

A 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.

4.74 out of 5 average rating, 104 reviews

The Crystal Loft

4.93 out of 5 average rating, 70 reviews

A cozy living area features a wood-burning fireplace with a flat-screen TV above. A foldout queen murphy bed is neatly tucked against the wall. A sectional sofa, dark wood coffee table, and a patterned area rug complete the inviting space, with large windows offering views of the outdoors.

Apartment in Dover

Walk to main lift! The Handle Studio @ Mt. Snow!

4.95 out of 5 average rating, 83 reviews

An outdoor recreational area is illuminated at night, featuring a billiard table under a gazebo. Guests are seated around picnic tables, enjoying their time. Soft lighting enhances the ambiance, while the yard displays green grass and surrounding structures.

Apartment in Watervliet

Uptown Watervliet

A spacious living and dining area features a large wooden table and a cozy seating arrangement. A flat-screen TV is mounted above a fireplace, and natural light flows through windows, creating a bright environment. Textured rugs add warmth to the hardwood flooring.