Vacation rentals with a firepit in Lenox

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, 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!

4.94 out of 5 average rating, 110 reviews

An open kitchen and dining area feature a wooden dining table surrounded by black chairs. The space is illuminated by natural light from large windows, with a breakfast bar visible in the background. A neutral color palette adds warmth to the inviting layout.

Home in Pittsfield

Net Zero home with rustic Berkshire charm

Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

Apartment in Copake Falls

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.

4.9 out of 5 average rating, 352 reviews

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!

4.88 out of 5 average rating, 225 reviews

An open living space showcases wooden beams and natural light. A cozy seating area features a plush couch, patterned cushions, and a round coffee table. A dining area is visible, complemented by a well-equipped kitchen in the background. A ship ladder leads to a sleeping loft above.

Cabin in Stockbridge

Hip Stockbridge Cabin - A stroll to the lake

Hello hip, glamping cabin! The decor is chic & bohemian cool! Enjoy the large yard & sunny deck. Fieldstone fireplace w/ vaulted ceilings & skylights. Cottage has beautiful pine throughout w/ fabulous interior design picks. Enjoy the sweet reading nook, master bedroom w/ skylights or put on a favorite record. Kids will love the sleeping loft. A 9 minute walk or 2 minute drive to lake public beach (The lovely Stockbridge Bowl) . BBQ grill, outdoor fire pit . Gates of Tanglewood minutes aaway!

4.9 out of 5 average rating, 284 reviews

A detached red barn is surrounded by a grassy yard, with patches of snow visible on the ground. The property features a gravel driveway leading to the barn's double garage doors. Mature trees line the background, offering a natural setting.

Guesthouse in Lenox

The Coach House | Modern 2BR Loft + Views & Pool

Restored coach barn with 25-ft cedar ceilings, skylights, and mountain views—part of House on Golden Hill, a historic Lenox farmhouse compound. This airy 2BR + loft retreat blends rustic charm with modern ease. Enjoy a full kitchen, cozy living space, and outdoor area. Set beside a stream with seasonal pool access, it’s perfect for families, couples, or creative escapes. Centrally located and just minutes to downtown Lenox, Tanglewood, and trails—your Berkshires base for rest and inspiration.

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.

4.96 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!

Vacation home in Great Barrington

An open, airy space features a wooden staircase leading to the upper level. A small dining area includes a table and two stools, while a comfortable seating area is visible in the background. Natural light filters through large windows, illuminating the modern design.

4.94 out of 5 average rating, 244 reviews

Home in Great Barrington. Steps from downtown!

First Things First… Let’s Keep the Love Alive! ❤️ 🙌 Central and Private! Just steps away from historic downtown Great Barrington. East Mountain Hiking trails are a quick walk away. Enjoy sunset views with friends and family, before you walk into town for a night out! Butternut Ski Area: 5-10 min drive(traffic depending) Tanglewood: 20-25 min This new home features all new appliances and furniture. Enjoy luxury, charm, and privacy while you rest easy at The Maple. 🫶

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.

4.99 out of 5 average rating, 298 reviews

Home in Lee

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relax by the firepit- we hope you enjoy your stay and will visit us again.

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.

Popular amenities for Lenox fire pit accommodations

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a fire pit

4.88 out of 5 average rating, 304 reviews

A single-story wooden lodge with a green metal roof is set amidst a grassy area. The exterior is lined with windows, allowing natural light to fill the interior. Surrounding trees provide a backdrop, and a paved driveway leads to the entrance, enhancing accessibility.

Home in Pittsfield

Dancing Horse Lodge

4.97 out of 5 average rating, 359 reviews

A bright living space features a white sofa with light striped cushions, complemented by a wooden coffee table. A dining area with a light wood table and chairs is present. Large glass doors open to a scenic outdoor view, enhancing the open and airy ambiance.

Home in Germantown

Private Cottage/Mountain Views/Trails/Fire pit

4.96 out of 5 average rating, 208 reviews

A tranquil lake scene is presented, with calm waters reflecting greenery from the surrounding trees. A wooden dock extends into the lake, while a selection of houses is visible in the distance, nestled among the landscape.

Home in Copake

Lakefront +pets +skiing +bbq +firepit +games

4.99 out of 5 average rating, 110 reviews

A light-filled open living area features a large sectional sofa arranged around a coffee table, with a soft rug underfoot. Two expansive windows provide views of the greenery outside. A dining space with high chairs is visible in the background, enhancing the inviting atmosphere.

Home in Great Barrington

Private Home in The Berkshires (New 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

4.95 out of 5 average rating, 201 reviews

A bright living area features a yellow couch and two accent chairs, inviting relaxation. A patterned area rug centers the space, while natural light filters through large windows. A staircase is visible in the background, along with decorative plants and artwork adorning the walls.

Home in Pittsfield

Cantabile life in the Berkshires

4.98 out of 5 average rating, 101 reviews

A spacious living area features a large, cushioned sectional sofa in a warm hue, complemented by a round coffee table. Natural light floods through tall windows, highlighting a minimalistic bookshelf and a stylish armchair in the corner, enhancing the room's cozy atmosphere.

Home in Hudson

Chic Hudson Farmhouse w/ Fireplace & Porch

4.89 out of 5 average rating, 134 reviews

A two-story house is set amidst greenery, featuring a fenced yard with varied foliage. A spacious deck equipped with a red umbrella is visible. A sunken fire pit is highlighted in the garden area, surrounded by trees and bordered by a quiet road.

Home in Craryville

The Gatehouse at Raspberry Ridge

Apartment rentals with a fire pit

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

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"

4.92 out of 5 average rating, 363 reviews

A well-lit patio space features a wooden table with a gas fire pit at its center, surrounded by four wicker chairs. Natural stone walls and a flower-adorned fence provide a backdrop, while soft lighting enhances the cozy atmosphere.

Apartment in Saugerties

Saugerties Village home with great backyard!

4.99 out of 5 average rating, 206 reviews

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.

Apartment in North Adams

Overlooking the city in a quiet 7 unit building.

4.95 out of 5 average rating, 199 reviews

The kitchen features a blend of modern cabinetry and original brick walls, showcasing a clean, functional design. Open shelving displays glassware and plants. A window allows natural light to fill the space, and a patterned rug adds comfort underfoot.

Apartment in Troy

Luxury downtown penthouse, by Franklin Plaza.

4.92 out of 5 average rating, 131 reviews

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.

Apartment in North Adams

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

4.96 out of 5 average rating, 137 reviews

Two pinball machines are positioned against a dark blue wall, featuring vibrant art and illuminated playfields. The machines offer a mix of classic and modern designs. A person stands nearby, engaging with the machines, while additional board games are visible on shelves in the background.

Apartment in Troy

Retro Pinball Arcade/Board Game AirBnB

4.96 out of 5 average rating, 119 reviews

A lush, green lawn gently slopes toward a small pond, framed by trees on either side. The natural foliage provides shade and privacy, while a stone is visible among the undergrowth. The area is serene, inviting reflection and connection with nature.

Apartment in Otis

Enjoy every season the Berkshires have to offer.

Cabin rentals with a firepit

4.93 out of 5 average rating, 255 reviews

An inviting bedroom is adorned with warm knotty pine walls and features a queen bed with decorative pillows. Two windows allow natural light to fill the space, with bedside lamps providing additional illumination. A cozy ottoman sits at the foot of the bed, complementing the rustic decor.

Cabin in Copake Lake

Secluded Cabin w/ PRIVATE HOT TUB and LAKE ACCESS

4.97 out of 5 average rating, 116 reviews

A spacious living area features vaulted wood ceilings and a mix of natural wood and stone finishes. A comfortable couch and chair are arranged around a central coffee table, with a warm glow from the fireplace adding to the cozy ambiance. Light enters through large windows.

Cabin in Chesterfield

Hilltown Cabin Hideaway: A River Runs Through It!

5 out of 5 average rating, 147 reviews

An inviting living space features a modern wood stove as its focal point. Large windows allow natural light to fill the room, revealing views of the surrounding trees. Two comfortable sofas are arranged for relaxation, with a hanging planter adding a touch of greenery.

Cabin in Ancram

The Ancram A - Luxury Mid-Century Modern Cabin

4.94 out of 5 average rating, 107 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

4.85 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

4.96 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

4.97 out of 5 average rating, 112 reviews

The modern cabin is illuminated by string lights, creating a warm ambiance against the dark backdrop of surrounding trees at night. The deck extends outward, providing a welcoming entrance, while large windows hint at the interior’s cozy atmosphere.

Cabin in Red Hook

Secluded luxury: modern riverfront fishing cabin