Holiday rentals with a fireplace in Williamstown

4.95 out of 5 average rating, 244 reviews

An open living space with a high wood-beam ceiling is displayed. A large stone fireplace serves as a focal point, surrounded by comfortable seating. A kitchen island with stools offers additional space. Large windows allow natural light to fill the room, enhancing the inviting atmosphere.

Farm stay in New Lebanon

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

4.98 out of 5 average rating, 151 reviews

A charming yellow house features a welcoming front porch, adorned with potted flowers and comfortable seating. Generous windows allow natural light to brighten the space. The well-maintained landscaping includes trimmed hedges and a stone pathway leading to the inviting entrance.

Home in Williamstown

Quality, Comfort, Charm in Williamstown Center

Stay at this completely renovated house in the center of Williamstown! Conveniently located in a quiet neighborhood within easy walking distance to the town center, Williams College and The Clark Art Institute. The house was fully renovated in 2021. All new everything including appliances, a luxurious tile shower, fresh sheets and towels and lovely furnishings, all to make your stay comfortable and cozy. The living room has a beautiful gas fireplace and smart tv and in the summer, central air.

4.94 out of 5 average rating, 136 reviews

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"

This beautiful, spacious, and historic property was formerly the Inn at Oak Hill. It is convenient to Williams College, Williamstown Theater Festival, Clark Art Museum, MassMOCA, FreshGrass Festival, BerkshireStock, Jiminy Peak, Bennington College, VAST snowmobile system and many other destinations in southern Vermont and western Massachusetts. Comfortably furnished with modern amenities such as Wi-Fi and satellite TV, our home also surrounds you with beautifully preserved & original features.

Place to stay in North Adams

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.

4.93 out of 5 average rating, 166 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.

4.92 out of 5 average rating, 186 reviews

A bright dining area features a large table surrounded by four chairs. Natural light filters through multiple windows, highlighting the warm wood floor. Potted plants are positioned near the windows, and wall art adds a touch of color to the neutral space.

Home in North Adams

A paradise in the woods, minutes from MASS MoCA

Stay and wake up to the magic Berkshire sunlight ! Nestled on a quiet hill on the back of MassMoca, this house is only 3 minute drive from downtown. It was renovated in 2021 with brand new wood floors in the living room and master bedroom, and an updated bathroom with hot tub. This is a second home to the owners, who sometimes come to the area for work, the arts, and the outdoors. They treat every corner of the house with love and care, and want to share this serene experience with you.

4.96 out of 5 average rating, 343 reviews

A rustic cabin constructed with wooden planks and stone features is nestled among tall trees. Lush greenery surrounds the cabin, while a stack of logs is positioned in the foreground. A gravel pathway leads up to the entrance, enhancing the natural setting.

Cabin in West Sand Lake

The Lodge at June Farms

Enjoy a 3rd night for FREE when you book 2 nights! The Lodge at June Farms is a stunning, rustic, open-floor-plan retreat. The screened-in front porch looks down onto our beautiful horse pasture. This main cabin is our most romantic cabin on the property. Our gigantic rain shower in the bathroom has an 8'x5' wall mirror and a French door that opens out to the forest. If you are a cook, this cabin is a chef's dream. Please check the availability for our other luxury cabins if booked!

4.92 out of 5 average rating, 256 reviews

Home in Adams

1890 House

Back online after renovations. This beautiful Victorian farmhouse is situated on a 1/2 acre with great views of Mount Greylock, surrounding mountains and quaint town of Adams. The wraparound porch is perfect for relaxing. It is fully furnished and has a fully equipped kitchen. There is a wood stove in living room. Walking distance to Adams/supermarket. Short drive North Adams (MASSMoCA), Williamstown (Clark Museum) and Jiminy Peak (ski resort) which is 30 minutes drive.

4.88 out of 5 average rating, 155 reviews

The exterior of a charming yellow cottage is visible, featuring dark green shutters and a welcoming porch with decorative elements. A well-kept garden with colorful flowers and greenery surrounds the cottage, while a gravel pathway leads to the entrance under a partly cloudy blue sky.

Cottage in Monroe

Pumpkin Pine Cottage: your next adventure awaits!

Explore the Deerfield River Valley and Hoosac Range from this tranquil base. Close to skiing, snow tubing, snowshoeing, hiking, birding, kayaking, white-water rafting, fly fishing, zip lines, and more. Like bikes? Amazing gravel, road, and MTB offerings await. Seek culture? Mass MOCA, Clark Art Institute, Northampton, Shelburne Falls, and the Berkshires are a short drive away. Covered bridges, farm stands, sugar shacks, and waterfalls are too plentiful to count!

4.98 out of 5 average rating, 147 reviews

The historic Gate House is framed by lush greenery and a manicured lawn, set against a vibrant sunset sky. Its stone façade and charming architecture are accentuated by soft lighting that bathes the exterior in warmth, inviting guests to explore the expansive outdoor space.

Home in Bennington

The Gate House--Experience Vermont!

The Gate House is a historic property located at the foothills of Mt Anthony. Built in 1865, the original structure of the house served as the gate house to the Colgate Estate, one of the most beautiful properties in Southwestern Vermont. Our home is just a few short miles to downtown where you can find local restaurants and breweries. We are not far from some of the best skiing/riding in the Northeast at Mt Snow, Bromley, Stratton and Prospect Mountains.

4.94 out of 5 average rating, 272 reviews

A group of twelve alpacas stands in a lush outdoor setting, showcasing various colors including white, brown, black, and grey. A wooden structure is visible in the background, surrounded by greenery and fencing.

Farm stay in Hoosick

Airbnb @ Sweet & Savory Farmette

Welcome to the AirBnB situated on a small working farm. You are welcome to tour the grounds to say hello to all the animals. This place is for the birds! No really you will enjoy watching chickens, ducks, emus, geese, guinea fowl, and peafowl. The farm is also home to a herd of beautiful alpaca and resident llama, curious goats, and barn cats. There are working livestock guardian dogs who watch over the herd who will greet you from behind the fence.

4.96 out of 5 average rating, 622 reviews

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.

Apartment in North Adams

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.

4.99 out of 5 average rating, 101 reviews

A living area features a stone fireplace with a roaring fire, surrounded by large windows that invite natural light. A circular coffee table rests on a textured rug, while comfortable seating options include an upholstered chair and wooden accent chairs, complemented by soft lighting.

Cottage in Bennington

Cozy, bright 3-bedroom Cottage with fireplace.

Cozy, spacious brook-side cottage with 3 bedrooms, 2 baths, fully-equipped kitchen, fireplace, and serene, 382-acre country setting. Colorful artwork, designer furnishings, and well-appointed kitchen and bathrooms will make you feel welcome and at home. Historic charm of Bennington ten minutes away. NYC (182 miles); Boston (118); Mt. Snow (32); Prospect Mountain (13). Close to MASS MoCA (22), Tanglewood (49) and Manchester outlets (32).

Popular amenities for Williamstown Accommodation with Fireplace

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a fireplace

4.99 out of 5 average rating, 168 reviews

A vintage-style freestanding bathtub is filled with water, complemented by a wooden tray featuring a book and a glass of white wine. A soft glow is provided by a candle placed nearby, enhancing the serene atmosphere of the bathroom.

Home in Dalton

Cleveland House - renovated Berkshires' gem.

4.93 out of 5 average rating, 114 reviews

The contemporary cabin features an elevated design with wooden walls and large glass windows. A spacious porch includes seating for relaxation. The surrounding grassy area is complemented by natural landscaping, with fire pit seating visible in the background.

Home in Jamaica

The Post Haus: one-of-a-kind modern VT experience

4.83 out of 5 average rating, 109 reviews

A charming yellow house is nestled among snow-covered trees, framed by tall evergreens. A snow-blanketed driveway leads up to the entrance, inviting visitors into a serene winter retreat in a wooded setting.

Home in Stratton

Stay mins from Mt. Snow & Stratton w/ EV charger

4.95 out of 5 average rating, 263 reviews

An open kitchen and dining area feature rustic wooden beams and warm wooden floors. A round dining table with black chairs is positioned near double glass doors leading to a deck. An island with stools offers additional seating, with kitchen amenities visible in the background.

Home in Ghent

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

4.99 out of 5 average rating, 123 reviews

The colonial home features a classic white exterior with black shutters and a welcoming front porch. An American flag is displayed prominently, and soft outdoor lighting highlights the entrance. The well-maintained lawn includes neatly trimmed bushes, creating a warm first impression.

Home in Sandgate

Country Colonial Home with rolling fields & stream

4.86 out of 5 average rating, 221 reviews

A rustic red barn stands among lush greenery, featuring large glass doors inviting natural light inside. The path leading to the barn is lined with gravel, and a stack of wood is neatly arranged beside the structure.

Home in Cheshire

19th c. Barn in The Berkshires

4.93 out of 5 average rating, 197 reviews

An open living space features high wooden ceilings with exposed beams and a stylish pool table positioned at the center. A cozy couch sits nearby, with a staircase leading to a loft area visible in the background. Natural light fills the room through large windows.

Home in Dalton

Brooksong, the perfect Berkshires getaway

4.94 out of 5 average rating, 135 reviews

The exterior of a two-story yellow house is set among trees under a clear blue sky. A full-width porch with simple wooden chairs and a table invites relaxation. Sunlight filters through the foliage, creating a tranquil atmosphere around the property.

Home in Ghent

Blacksmith House - Charming Historic Getaway

Apartment rentals with a fireplace

4.97 out of 5 average rating, 100 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

4.96 out of 5 average rating, 103 reviews

Apartment in Bennington

Suite Sunset 311 Rice Lane Bennington VT

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

4.99 out of 5 average rating, 171 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

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

4.88 out of 5 average rating, 102 reviews

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

Hist. Troy River acc. Modern Apt

4.88 out of 5 average rating, 272 reviews

A spacious living area is presented with exposed wooden beams and wide pine floors. A comfortable couch faces a welcoming dining area, where a large table is set for meals. Sunlight streams through a window adorned with sheer curtains, enhancing the cozy ambiance.

Apartment in Ashfield

Zachariah House Main St. Ashfield

4.88 out of 5 average rating, 145 reviews

A rustic wooden cabin exterior is shown, featuring a balcony on the upper level. Two garage doors are visible below, with a small seating area made of metal in the foreground. Lush green grass surrounds the cabin, framed by trees.

Apartment in Arlington

Brian Peace of Heaven

Other holiday rentals with a fireplace

4.93 out of 5 average rating, 113 reviews

A chalet-style home is surrounded by lush greenery, featuring a large three-sided wrap-around deck. Tall windows dominate the front, allowing ample natural light. To the side, a wooden garage complements the main structure, set against a backdrop of trees and an expansive lawn.

Chalet in Stamford

Peaceful VT Chalet w/ Mountain View’s

4.98 out of 5 average rating, 56 reviews

A cozy cottage is positioned amidst a lush field of wildflowers, with vibrant greenery surrounding it. The blue exterior of the cottage complements the clear blue sky and mountains in the background, creating a serene and inviting environment.

Cottage in Pownal

Beautiful, 100 Acre Retreat, Williamstown 10 Mins

5 out of 5 average rating, 4 reviews

Home in Williamstown

New Luxe Downtown Cottage | Walk to Shops & Dining

Cottage in West Sand Lake

The living area features a green couch and a wooden coffee table, complemented by a comfortable rocking chair. A flat-screen TV is positioned on a media console. Natural light filters through large windows framed by sheer curtains, illuminating the vaulted knotty pine ceiling.

4.99 out of 5 average rating, 114 reviews

Cozy Cottage near lake

4.85 out of 5 average rating, 306 reviews

An old-fashioned cedar hot tub is positioned on a wooden deck, surrounded by trees displaying autumn foliage. The peaceful outdoor setting offers a serene atmosphere for relaxation.

Cabin in Stephentown

Cabin in the woods w cedar Hot Tub + private pond

4.93 out of 5 average rating, 56 reviews

A charming red barn stands against a backdrop of trees, with a gently sloping roof and a well-kept grassy area in the foreground. The scene is complemented by a colorful autumn sky at dusk, surrounding the structure with a peaceful ambiance.

Barn in Florida

The Red Barn- close to ski mountains & museums

5 out of 5 average rating, 32 reviews

A spacious yard is shown with a variety of trees, framed by a vibrant sunset sky. A comfortable seating area with chairs is positioned on the grass, offering views of the home and surrounding landscape, blending nature with the warm invitation of the evening.

Home in Bennington

VT at its best! - near museums, trails & colleges