Apartment holiday rentals in Williamstown

4.95 out of 5 average rating, 370 reviews

Chic Downtown Studio, Perfect for College Weekends

★ New to Williamstown? Explore our interactive guidebook. Charming studio just steps away from shops, restaurants & few minutes’ walk to Williams College. Renovated and well-equipped, this home offers a wonderful view of Water Street. If you like the outdoors, descend on the Green River back of the property. The wooded riverbank with Adirondack chairs, and picnic tables is great for relaxing while enjoying your evening sundowners by the fire pit with the sound of the river in the background.

LocationFamilyKitchen

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

Our happy place is a 5 minute walk to Berkshire East/Thunder Mountain . An 8 minute walk to the Deerfield River for guided fishing tours with Hilltown Anglers, kayaks, ,whitewater rafting. 10 minute walk to town and shuttle for tubing. A 5 minute drive to local wedding venues. We provide a full kitchen with all cooking essentials, a private picnic area with charcoal grill (charcoal provided). We reside at the single family home on property and we’re excited to share our Suite 23 !

LocationFamilyCheckout

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, 188 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.

FamilyLocationAir conditioning

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 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.

LocationValueAccuracy

4.94 out of 5 average rating, 133 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.

LocationValueCleanliness

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, 217 reviews

Overlooking the city in a quiet 7 unit building.

This is a quiet, 7 unit, newly renovated condominium building. We welcome quiet guests who will appreciate a relaxing stay and be conscious of others around them. We are within walking distance to the countries largest contemporary art museum. The 2nd floor is an open plan divided by the stair case. Each side has a queen bed, its own closet. The full bathroom is shared with the two beds. This is a loft, there are no full walls between the two sides of the loft.

LocationValueWi-Fi

4.99 out of 5 average rating, 135 reviews

The MoCA-Cabana: 2 bd + Sauna

Welcome to the MoCA-Cabana at Chase Hill—the historic estate of the owners of the factory that became MASS MoCA. More than just guest houses, Chase Hill is an experience: gardens, fire pits, sauna, occasional music rehearsals. Just a 5-minute walk to MASS MoCA, 10 mins by car to Williams & Clark. ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates often available beyond what the calendar shows—don’t hesitate to contact us!

LocationValueCheckout

4.92 out of 5 average rating, 324 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

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.

ValueFamilyComfort

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, 123 reviews

ALL welcome: Lovely 1 BR studio, Berkshires beauty

Come as you are - we welcome ALL visitors. Relax and soak in your surroundings in this new 1 bedroom vacation spot. Part of a barn conversion, the space is clean and bright and ideally located for those exploring all the Berkshires has to offer. Perfect for an individual or couple looking to escape to a serene and beautiful setting - a stream abuts the property and hiking/snowshoeing trails are accessible out the front door.

LocationValueAccuracy

4.92 out of 5 average rating, 199 reviews

Two wooden chairs are positioned on a grassy area, facing a gently sloping hill. A modern white farmhouse is visible alongside a deck with stairs. In the background, trees frame the serene landscape, and mountains are faintly visible under a cloudy sky.

Apartment in Bennington

Scenic Vermont Studio

This beautiful retreat is halfway between the ski slopes of southern Vermont and the cultural centers of Williamstown and North Adams, MA. The residence is a modern, spacious, basement apartment, part of an 1860 farm house. It has its own private entrance around the back of the house at ground level. Solar garden lights and motion detector lighting will illuminate your path to the apartment.

FamilyValueCondition

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, 362 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.

LocationValueCleanliness

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, 194 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 Williamstown apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

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

FamilyValueLong stay

A balcony deck is depicted with two blue Adirondack chairs facing a small round table. A floral centerpiece is placed on the table, which is accompanied by two glasses. The area is surrounded by lush green trees, creating a serene atmosphere.

4.98 out of 5 average rating, 142 reviews

Historic Victorian - Entire 3rd floor

ValueLocationWi-Fi

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.

4.96 out of 5 average rating, 180 reviews

Bennett Abode

LocationValueCondition

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

LocationFamilyTV

4.92 out of 5 average rating, 102 reviews

A curved driveway leads to a charming white multi-story house surrounded by lush green grass and trees. A well-maintained lawn and flower beds are visible. Additional buildings can be seen in the background, with vehicles parked nearby, suggesting ample parking space.

Apartment in Pownal

"The Chambers"

FamilyValueKitchen

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, 505 reviews

Private guest apartment. One block from downtown.

ValueLocationHospitality

4.8 out of 5 average rating, 101 reviews

A bright interior space features light-colored walls and large windows with flowing white curtains. A small wooden table with flowers is positioned beside a wall-mounted shelf. A kitchen area is visible in the background, while a warm wooden floor complements the overall aesthetic.

Apartment in Grafton

#2 at Grafton Inn

LocationFamilyParks

4.88 out of 5 average rating, 294 reviews

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

ValueFamilyCheckout

Private apartment rentals

4.97 out of 5 average rating, 109 reviews

A welcoming living area features a large gray couch adorned with decorative pillows, complemented by a vibrant yellow armchair. Wooden cabinetry in the kitchen area holds essential appliances, while a lush indoor plant adds a touch of greenery. Natural light enters through the windows, creating a cozy atmosphere.

Apartment in Greenwich

Cozy Riverside Apartment with Private Backyard

FamilyValueLaundry

4.98 out of 5 average rating, 535 reviews

A well-lit kitchen and dining area features a wooden dining table surrounded by six chairs. Light hardwood flooring complements the gray cabinetry. A potted plant sits on the table, and modern appliances are visible in the background, including a refrigerator and stove.

Apartment in Wilmington

**Happy Hour! Gorgeous & Modern Downtown Retreat**

LocationFamilyTV

The Victorian duplex features a symmetrical facade with large windows fitted with black shutters. The porch is bordered by slender trees, and shrubs are evenly placed in front, enhancing the inviting entrance. A clear blue sky provides a bright backdrop.

4.97 out of 5 average rating, 277 reviews

Spacious Victorian duplex near MASSMoCA, MCLA (19)

LocationValueDecor

4.95 out of 5 average rating, 300 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

LocationValueAccess

4.92 out of 5 average rating, 807 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

ValueFamilyLong stay

4.95 out of 5 average rating, 194 reviews

A cozy living area features a light grey sofa paired with a wooden coffee table. An accent chair with a textured throw sits beside a basket. A large cow print hangs on the wall, with two framed pieces nearby. A patterned rug covers the floor.

Apartment in Bennington

Cooper's Place

LocationValueSolo travel

4.97 out of 5 average rating, 149 reviews

A modern living area features a teal couch paired with a mustard yellow chair. A round mirror hangs above a black accent wall, while a glass coffee table with golden legs sits on a textured area rug. Colorful abstract art adorns the walls.

Apartment in Troy

Clean & Quiet Apartment | Parking + WiFi

FamilyValueAccuracy

Superhost

The living room features a marble fireplace framed by decorative items. Two light-colored chairs are positioned around a round glass coffee table, which holds a floral arrangement and a few books. A dining table is set nearby, illuminated by natural light.

Apartment in Troy

4.86 out of 5 average rating, 130 reviews

Hist. Troy River acc. Modern Apt

FamilyLocationQuiet

Apartment rentals with a hot tub

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

ValueFamilyComfort

5 out of 5 average rating, 33 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

LocationValueSleep quality

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-In Ski-Out Loft Lift & MT. Views

ValueLocationHiking

4.99 out of 5 average rating, 75 reviews

An open-plan kitchen and dining area features wood cabinetry and stainless steel appliances. A rectangular dining table is surrounded by four chairs, with a multi-coloured striped rug laid on the floor. Natural light enters through large windows, enhancing the spacious atmosphere.

Apartment in Sunderland

Apartment in the Woods

LocationValueBarbecue

4.98 out of 5 average rating, 50 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

FamilyLocationSkiing

4.94 out of 5 average rating, 31 reviews

A spacious living area includes a large sectional sofa, a wooden dining table with chairs, and a flat-screen TV mounted above a fireplace. Natural light filters in through a large window, illuminating the soft beige walls and neutral carpeting.

Apartment in Stratton

Summit’s Stratton Sneak Away II

LocationFamilyAccess

4.89 out of 5 average rating, 9 reviews

Apartment in Stratton

Walk to Ski Lifts & Village | Hot Tub & Sauna

FamilyLocationHospitality