Apartment holiday rentals in Lanesborough

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, 116 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.

LocationValueAmenities

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.

4.94 out of 5 average rating, 192 reviews

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.

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4.9 out of 5 average rating, 233 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.

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4.94 out of 5 average rating, 135 reviews

Charming Farmhouse Apt Near Williams College

Relax in this charming New England farmhouse apartment just minutes from Williams College, Mass MoCA, and downtown Williamstown. This private second-floor retreat features original wood floors, a spacious bedroom with a comfortable queen bed, a fully equipped kitchen, and a peaceful setting perfect for couples, Williams College visitors, and Berkshire escapes. Enjoy easy access to local restaurants, hiking trails, museums, and the best attractions throughout the Berkshires.

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4.97 out of 5 average rating, 730 reviews

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!

LocationFamilyRiver

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, 329 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.

ValueFamilyCleanliness

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.

FamilyLocationParking

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.

LocationFamilyAccuracy

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.

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A modern kitchen is equipped with stainless steel appliances, including a refrigerator and oven. White cabinetry offers ample storage. A central island features a sink and prep space, complemented by a set of kitchen utensils. Natural light enters through a nearby window.

5.0 out of 5 average rating, 171 reviews

Downtown | Waterfront | Walk to Shops

★ New to Williamstown? Explore our interactive guidebook. One bedroom apartment, meticulously upgraded with the discerning guest's convenience in mind. The property is in the midst of Williamstown's popular spots: Williams College campus, theaters, museums, restaurants, shops, and golf course. It also sits by the rushing, sometimes tranquil, Green River where you can sit back, relax and enjoy the fire pit.

LocationValueLong stay

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.

4.94 out of 5 average rating, 367 reviews

Cold Spring - The White Door

Welcome to your peaceful Berkshire retreat. Originally a barn, this charming two-bedroom, one-bath apartment features a fully equipped kitchen, skylight-vaulted ceilings, and original wood beams. Just a short drive from Mount Greylock, Jiminy Peak, and the Williamstown Theatre Festival—surrounded by scenic hikes and great local dining, it’s the perfect home base for your getaway.

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The light-filled living room features a comfortable gray couch with decorative pillows, a vintage coffee table, and an eclectic mix of artwork on the walls. A television is positioned on a wooden stand, and diverse seating options are provided by antique chairs and a small dining table.

4.97 out of 5 average rating, 199 reviews

Charming Art Filled Apartment

Charming and quirky, this 2nd floor apartment in a 120 year old house is decorated with art and antiques, like the living museum of an eccentric friend. Or a mini theme park for the mind. We are just blocks from downtown North Adams, on the main road into town. It’s literally a 2 minute drive to MASS MOCA, or a ten minute walk. Dogs are always welcome!

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Popular amenities for Lanesborough apartment rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.96 out of 5 average rating, 225 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

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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.

4.96 out of 5 average rating, 105 reviews

"Nostalgia" a spacious2 bedroom first floor unit.

LocationFamilyCleanliness

5.0 out of 5 average rating, 201 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

FamilyLocationOutdoor spaces

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.

4.91 out of 5 average rating, 511 reviews

Private guest apartment. One block from downtown.

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Apartment in Great Barrington

A modern bedroom features a spacious bed with high-end linens, flanked by two stylish chairs. A desk and chair sit by the window, and an arched door adds architectural interest. Natural light illuminates the room, highlighting a unique wall design in neutral tones.

4.92 out of 5 average rating, 181 reviews

King Bed | Patio | 2m to Ski Resort

LocationValueAmenities

4.97 out of 5 average rating, 310 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

ValueLocationHiking

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

FamilyLocationDecor

4.95 out of 5 average rating, 304 reviews

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

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Private apartment rentals

4.88 out of 5 average rating, 360 reviews

A cozy bedroom is filled with natural light from two windows, dressed with blue curtains. A spacious bed with striped bedding is centered in the room. A white dresser and a television are positioned along the walls, creating a relaxing atmosphere.

Apartment in Stamford

Getaway Near Mass MoCA, Great Hiking, Scenic Views

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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, 220 reviews

Overlooking the city in a quiet 7 unit building.

ValueFamilyBathroom

4.92 out of 5 average rating, 816 reviews

A modern kitchen features white cabinetry and a green tile backsplash. A large island with yellow bar stools provides a casual dining space. Stainless steel appliances and hanging pots enhance the functionality. Natural light floods the area, reflecting on the polished hardwood floor.

Apartment in Troy

Modern Luxury & Victorian Charm: The Bird in Hand

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A garden scene is presented with a wrought-iron chair nestled among frosted pink and green sedum flowers. A leafless tree stands in the background, framed by autumn foliage. Rolling hills are visible beyond the landscaped area, hinting at the surrounding natural beauty.

4.98 out of 5 average rating, 129 reviews

ALL welcome: Lovely 1 BR studio, Berkshires beauty

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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

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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.

4.78 out of 5 average rating, 60 reviews

Spacious 2 bedroom downtown very nice area!

ValueLocationCleanliness

4.87 out of 5 average rating, 83 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

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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.

4.94 out of 5 average rating, 72 reviews

Modern Gem in the Heart of Berkshires

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Apartment rentals with a hot tub

4.91 out of 5 average rating, 208 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

LocationFamilyTV

4.95 out of 5 average rating, 55 reviews

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

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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

4.84 out of 5 average rating, 44 reviews

Mountainside Condo Ski on/off

LocationValueSleep quality

4.88 out of 5 average rating, 8 reviews

Apartment in Troy

Luxury Downt. Troy Apartments near Franklin Plaza.

LocationFamilyBackyard

4.96 out of 5 average rating, 52 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

Dover VT 2 Bdrm Condo - Mt Snow Shuttle

ValueFamilyParking

5.0 out of 5 average rating, 35 reviews

The entryway features a covered porch with a wooden deck. Two blue chairs adorned with floral cushions are positioned beside the door. A welcome sign is displayed on the wall, and colorful flowers flourish around the steps, enhancing the inviting exterior.

Apartment in Stillwater

Saratoga Getaway 2

LocationValueBiking

5.0 out of 5 average rating, 8 reviews

Apartment in Dover

Peaceful Ski Escape in Mountain Village

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