Holiday rentals with a fireplace in Sheffield

4.91 out of 5 average rating, 565 reviews

A charming two-story country cottage is shown, featuring natural wood siding and a welcoming entrance. A stone pathway leads to the front door, bordered by a manicured lawn and mature trees, embodying a peaceful rural setting.

Cottage in Craryville

Columbia County Getaway - Raspberry Ridge Cottage

Affordable, pet and family friendly country cottage in the Hudson Valley off TSP; close to Berkshires and Hudson. Amenities are high speed reliable internet, landscaped grounds, hilltop gazebo with dining deck, grill, fire pit and laundry facilities. Cosy wood-stove inside. Backyard chicken coop with fresh eggs. Go 'tree-bathing' on the deck. Woodland setting with open fields. Perfect for a low-key weekend getaway. Hosts live next door. Chief Martindale Diner walking distance. Ample parking

4.99 out of 5 average rating, 346 reviews

An exterior view of the renovated red barn features a sloped roof and white-trimmed windows. Two white Adirondack chairs adorned with pink cushions are positioned on the grass, under the shade of a nearby tree, providing a cozy outdoor seating area.

Loft in Great Barrington

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

4.95 out of 5 average rating, 439 reviews

A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.

Chalet in Otis

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

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!

4.96 out of 5 average rating, 373 reviews

A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.

Cabin in Red Hook

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

4.9 out of 5 average rating, 352 reviews

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.

Flat in Copake Falls

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

4.94 out of 5 average rating, 145 reviews

An open living area showcases rustic wooden beams and a cozy gas fireplace. A modern gray sofa faces the fireplace, complemented by a glass coffee table with a vase of pink flowers. Natural light floods in from the glass doors, leading to the lush green outdoor space.

Home in Stockbridge

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

Cottage in Great Barrington

A charming cottage is framed by vibrant flowering shrubs and greenery. The front porch is adorned with decorative elements, while large windows invite natural light into the space. A wooden fence encloses the front garden, enhancing the quaint and inviting atmosphere.

4.93 out of 5 average rating, 314 reviews

Artist Cottage

Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.

4.93 out of 5 average rating, 162 reviews

A spacious kitchen is equipped with white cabinetry and a large wooden island, featuring bar seating. Natural light floods the room through multiple windows. A dining table for six complements the space, with a fruit bowl as a centerpiece.

Cottage in Sheffield

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Tiny home in New Marlborough

4.94 out of 5 average rating, 119 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

4.97 out of 5 average rating, 354 reviews

A yellow sign is displayed among green foliage, featuring a goat and two ducks illustrated on it. The bold text indicates 'SLOW FREE RANGE DUCKS & GOATS at PLAY,' emphasizing the friendly atmosphere surrounding the property.

Farm stay in Ancram

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!

Cottage in Great Barrington

A bright living area is featured, showcasing large windows that provide views of the surrounding nature. A fireplace is positioned centrally, complemented by a light-toned wooden sofa and a cozy chair. A dining table for two is visible, along with a small shelf and potted plants.

4.93 out of 5 average rating, 167 reviews

The Cottage at The Barrington House

Welcome to the Cottage at the Barrington House! The Barrington House is nestled in the serene Berkshires Mountains - which have long been a sanctuary for weary city dwellers seeking breathing space, a perfect retreat for artists, writers and thinkers! It's sprawling grounds offer stunning views of lush valleys and distant peaks, while the interior features a fireplace, cozy reading nook, and unlimited windows that invite the natural world inside.

Popular amenities for rentals with a fireplace in Sheffield

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a fireplace

4.91 out of 5 average rating, 144 reviews

The exterior of the log cabin features natural wood siding and a stone chimney. An American flag hangs from the wall, and a wooden deck leads to the entrance. Surrounding greenery adds a touch of nature to the cozy setting.

Home in Copake

Modern, cozy log cabin in Copake

4.97 out of 5 average rating, 212 reviews

The exterior of a spacious house is shown, featuring a light-colored facade and a neatly landscaped yard. A winding pathway leads to the entrance, surrounded by lush greenery and colorful flowers. A large window reflects the natural light filtering through the trees.

Home in Millerton

Vacation Home In Millerton

4.95 out of 5 average rating, 135 reviews

A charming home is set on a raised stone foundation, featuring a bright blue front door that adds a pop of color. Lush green grass surrounds the property, complemented by a stone walkway leading to the entrance. Mature trees and yellow forsythia bushes provide a natural backdrop.

Home in Great Barrington

The Hideaway: Berkshire Home - village of Egremont

4.94 out of 5 average rating, 105 reviews

An open loft space showcases bright white wooden floors and a beamed ceiling. A comfortable couch and a hammock chair are positioned among large windows, allowing natural light to fill the room. Potted plants add a touch of greenery, while a wooden coffee table anchors the seating area.

Home in Lakeville

The Barn - Rustic Chic Loft, Hotchkiss, Lakes, Ski

4.94 out of 5 average rating, 146 reviews

A cozy living area features a stone fireplace with a warm fire, surrounded by wooden cabinetry and appliances. Brightly colored striped couches flank a wooden coffee table, while natural light streams in through a large window. Pendant lights add an inviting glow to the space.

Home in Ancramdale

Unwind in the country, stargaze in hot tub

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

4.92 out of 5 average rating, 143 reviews

A spacious living area is visible from above, featuring a tan leather couch, a gray armchair, and a brown coffee table. A woodburning stove is positioned against a dark tiled wall, with a Smart TV mounted nearby. Light pours in from adjacent windows, illuminating the area.

Home in Monterey

Berkshires Cottage | Trails & Water Nearby

4.92 out of 5 average rating, 279 reviews

The interior space showcases exposed wooden beams and a bright, open layout. A comfortable seating area is positioned near large windows that provide natural light and views of the surrounding trees. A round dining table is visible, accompanied by a set of stylish chairs.

Home in Cornwall

Secluded modern forest cabin with private brook

Apartment rentals with a fireplace

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.

Flat in Plainfield

Sunny, light filled loft in 1873 Colonial

4.94 out of 5 average rating, 290 reviews

A bright living area features a comfortable gray sofa complemented by colorful accent pillows. A black lounge chair sits beside a marble coffee table. Large windows allow plentiful natural light, and a sleek wood stove adds warmth to the space.

Flat in Hudson

Romantic Warren St Penthouse w/Catskill Mtn Views

4.9 out of 5 average rating, 138 reviews

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.

Flat in Lanesborough

Cozy Rustic Apt. in 18th c. Berkshire Farmhouse

4.77 out of 5 average rating, 229 reviews

A charming exterior of a one-story house is surrounded by vibrant red trees. A welcoming porch features rocking chairs, while a stone pathway leads to the entrance. Lush greenery is visible in the yard, along with a small seating area occupying the lawn.

Flat in Rhinebeck

Rhinebeck Village Apartment

4.92 out of 5 average rating, 100 reviews

A spacious living room features two upholstered chairs and a round coffee table topped with fruit. A decorative area rug in warm colors covers the floor, while a large, modern television is mounted above a decorative fireplace. Bookshelves are visible in the background.

Flat in Nassau

A Haven of Rest Beautiful Historic Tranquil Suite

4.93 out of 5 average rating, 202 reviews

An outdoor patio area features a stone surface surrounded by colorful flower beds. A round table with chairs and a large umbrella provide seating, alongside a charcoal grill. The home's entrance is highlighted by a welcoming red door and large windows.

Flat in Great Barrington

Secluded but not isolated Berkshire Retreat

4.9 out of 5 average rating, 329 reviews

The spacious living area features warm wooden flooring and exposed brick walls. A gas fireplace is positioned centrally, surrounded by comfortable seating. Dining furniture is visible nearby, along with a staircase leading to upper levels, illuminated by natural light from multiple windows.

Flat in Hudson

Warren St. Ensuites - Pets allowed

4.85 out of 5 average rating, 173 reviews

A well-equipped kitchen showcases modern appliances, including a refrigerator and microwave. Gray cabinetry provides ample storage, while a small window allows natural light to brighten the space. Decorative items and a plant add a welcoming touch, complemented by a patterned mat on the floor.

Flat in Catskill

The Hideaway| cozy studio in Catskill village

Other holiday rentals with a fireplace

4.91 out of 5 average rating, 23 reviews

A spacious living area features high, vaulted ceilings and large windows that frame views of the outdoors. Two comfortable sofas are arranged around a central area rug, with a stone fireplace serving as a focal point. Shelving units display various decorative items, while a light floor lamp adds illumination.

Home in Great Barrington

Valley Vista atop Jug End

5 out of 5 average rating, 21 reviews

A bright living area features large glass doors opening to a scenic view of greenery. A spacious grey sofa and a black armchair are arranged around a modern coffee table. Exposed wooden beams and a brick fireplace add character to the room, enhancing the tranquil atmosphere.

Barn in Sheffield

Modern Dairy Barn

5 out of 5 average rating, 77 reviews

The screened porch is illuminated at dusk, showcasing wooden walls and ceiling. Several seating options are visible, including wicker chairs and a dining table. A warm, inviting atmosphere is created by the soft lighting, enhancing the sense of outdoor comfort in the serene setting.

Cottage in Sheffield

The Blue Elm A Historic Country Cottage

4.97 out of 5 average rating, 38 reviews

The historic house is set against a backdrop of rolling mountains, surrounded by lush greenery and flower gardens. A tranquil lawn stretches before the home, which features large windows and a welcoming front porch, inviting guests to explore the expansive property.

Home in Sheffield

Private Berkshires Estate w/ Tennis Court

4.94 out of 5 average rating, 108 reviews

A serene pond reflects the surrounding greenery, with kayaks resting on the shore. A cozy cabin is visible in the background, framed by trees. The tranquil setting invites outdoor activities such as swimming or fishing, creating a peaceful natural atmosphere.

Cabin in Colebrook

Rustic Pond Cabin: Nature, Stars & Serenity

4.84 out of 5 average rating, 25 reviews

An aerial view of a private home nestled among vibrant trees that showcase fall colors. The house features a light exterior with a spacious lawn, surrounded by a field and dense foliage, offering a peaceful retreat in nature.

Home in Sheffield

Whitney by AvantStay | Private Berkshires Estate

4.8 out of 5 average rating, 87 reviews

A charming blue cottage is nestled among vibrant autumn foliage. The two-story structure features a mix of gabled roofs and a covered porch. Lush greenery surrounds the gravel driveway, enhancing the serene setting.

Cottage in Sheffield

Charming Handcrafted Cottage in the Berkshires!