Holiday rentals with outdoor seating in Becket

4.95 out of 5 average rating, 466 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

Great locationWell-equipped facilitiesClean

4.97 out of 5 average rating, 109 reviews

Home in Becket

Nerd Preservation Sanctuary

Nerdscapist, geekmantic country home; perfect for oddballs who wish for a crafty, private, hilarious country retreat. Featuring a bad art print collection from the glorious MA Museum of Bad Art (Or Mass MOBA). Original bad art and sculpture. Much scope for the imagination's doofiest crevices. Redonkulously close to all the local fun: tiny drive to 5 lakes, Jacob's Pillow, Tanglewood 17 mi, Otis ski, 1/2 hr to Butternut Ski & Tubing Pittsfield & Great Barrington, hour to Berkshire E & Mass MOCA.

Great locationQuiet surroundingsStylish design

4.95 out of 5 average rating, 305 reviews

A calm lake reflects vibrant autumn foliage, with trees displaying shades of red, orange, and yellow. A boat is anchored near a wooden dock, and the surface of the water mirrors the colorful landscape, creating a serene and picturesque scene.

Cottage in Becket

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. Approved pet = approved Pet Agreement.

Great locationFriendly hostExcellent service

4.91 out of 5 average rating, 130 reviews

A view from a framed window reveals a cozy living space featuring a vintage wood-burning stove. A green sectional sofa provides seating, complemented by a light wood coffee table. Natural light fills the room, highlighting the open layout connecting to the kitchen area.

Cottage in Becket

Stylish Shales Brook Cottage-Cozy up to happiness

Bright & inviting! Welcome to our charming cottage, a stylish 2-bedroom, 2-bath retreat by Shales Brook. Relax on cool evenings beside the vintage Malm wood-burning stove. Enjoy modern comforts with central air, a screened-in porch, and a deck overlooking the tranquil waters of Shales Brook. The soothing sounds of the brook enhance your stay.. Located near fabulous Berkshire attractions, fantastic hikes, 15 minutes to the town of Lee, minutes to Jacob‘s pillow and 20 minutes to Tanglewood,!

Great locationStylish designExcellent service

4.99 out of 5 average rating, 126 reviews

A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.

Home in Staatsburg

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Great locationQuiet surroundingsWell-equipped facilities

4.97 out of 5 average rating, 116 reviews

An expansive view of rolling hills and distant mountains is visible through a treeline, with a foreground of manicured green grass and apple trees. The cabin's wooden structure is partially seen on the right, enhancing the connection to nature.

Cabin in Williamsburg

Mountain Retreat close to Northampton & Amherst!

Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.

Great locationStylish designWell-equipped facilities

4.83 out of 5 average rating, 133 reviews

A contemporary cedar home is set on a spacious green lawn surrounded by trees. The two-story structure features a large front porch and a combination of wooden and glass elements, enhancing its integrated design with nature. A gravel pathway leads to the entrance.

Cabin in Becket

Wildlife Retreat in the Forest

Home in the Birkshires! 12 minutes away from Jacob's Pillow, 2.5 hours away from NYC. Our Beautiful Lindal Cedar Contemporary home has everything you'll need. It is tucked away on a private 9+ acre estate with 4 large bedrooms, 2.5 baths. The Master Bedroom can be your own private getaway with 2 balconies. One overlooks the large living room with floor to ceiling windows and stone fireplace. The other overlooks the expansive property. It's definitely a tranquil place to rest and relax.

Great locationCleanStylish design

4.94 out of 5 average rating, 267 reviews

A firepit area is surrounded by several light blue chairs, set on a pebbled ground. The calm lake reflects the trees and landscape, creating a serene outdoor space ideal for gathering and relaxation.

Cottage in Becket

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit (access via uneven steps) • Canoe & 2 kayaks • Smart TV & 4 Google smart speakers • 1 Gigabit Wi-Fi • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Great locationStylish designWell-equipped facilities

4.99 out of 5 average rating, 306 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 relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Great locationGreat stayFriendly host

4.96 out of 5 average rating, 123 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.

Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

Great locationCleanQuiet surroundings

4.99 out of 5 average rating, 295 reviews

A two-story home is depicted, featuring a grey wooden exterior with multiple windows. A wooden deck with stairs leads to the entrance, surrounded by green grass and vibrant yellow flowers. The clear blue sky complements the inviting structure.

Farm stay in Pittsfield

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Great locationExcellent serviceNear markets

4.95 out of 5 average rating, 109 reviews

Home in Becket

HOT TUB! Berkshires: Dog & Family Friendly!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch -Generator on site

Popular amenities for Becket outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.98 out of 5 average rating, 124 reviews

A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.

Home in Rhinebeck

Slate Cabin - Stylish Country Escape x Rhinebeck

Great locationGreat stayStylish design

4.97 out of 5 average rating, 384 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

Scandinavian Cottage/Mountain Views/Fire pit

Great locationGreat stayStylish design

4.92 out of 5 average rating, 174 reviews

The front of the house is framed by lush greenery and a vibrant red maple tree. A welcoming red staircase leads to the entrance, while large windows allow natural light to illuminate the interior. The roof is partially covered with clouds, enhancing the outdoor serenity.

Home in Otis

The Pinnacle House at Otis Ridge Ski Area!

Great locationQuiet surroundingsStylish design

4.94 out of 5 average rating, 159 reviews

A spacious living area features a large sectional couch surrounding a coffee table, with a stone fireplace serving as a focal point. Natural light enters through multiple windows, highlighting the open floor plan and wooden elements throughout the space.

Home in Otis

Berkshires hideaway! Summer serenity

Great locationStylish designWell-equipped facilities

4.98 out of 5 average rating, 112 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

Great locationQuiet surroundingsGreat stay

4.95 out of 5 average rating, 210 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

Great locationGreat stayNear markets

4.97 out of 5 average rating, 231 reviews

A serene riverside deck features two striped lounge chairs, positioned for optimal views of the Connecticut River. Lush greenery frames the scene, and flower pots add a touch of elegance. The wooden deck offers a natural and inviting space to relax by the water.

Home in Agawam

Sunrise on the Water's Edge - Riverside Bungalow

Great locationWell-equipped facilitiesFriendly host

4.95 out of 5 average rating, 476 reviews

A spacious interior features exposed wooden beams and light-colored flooring. Large windows allow natural light to illuminate the room, highlighting comfortable seating areas and a dining table. A staircase is visible, leading to the upper level, enhancing the open and airy design.

Home in Germantown

Rustic Swedish Barn/Featured in Airbnb Magazine

Great locationWell-equipped facilitiesExcellent service

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 294 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

Great locationGreat stayClean

4.99 out of 5 average rating, 185 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

Great locationQuiet surroundingsStylish design

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, 160 reviews

Bennett Abode

Great locationQuiet surroundingsFriendly host

4.89 out of 5 average rating, 285 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

Great locationCleanFriendly host

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, 364 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Great locationQuiet surroundingsExcellent service

Apartment in Great Barrington

A modern bedroom showcases a spacious bed with crisp white linens. Accent lighting frames the walls, and a patterned area rug adds warmth to the space. A compact seating area with stylish benches complements the décor, while an entrance leads to a private bathroom.

4.9 out of 5 average rating, 136 reviews

King Bed | Stylish | Wi-Fi | *2m Ski Resort*

Great locationWell-equipped facilitiesGreat stay

5 out of 5 average rating, 395 reviews

A spacious living area features comfortable seating, a glass coffee table, and a dining space with wooden chairs. The kitchen is visible, showcasing modern appliances and a light wood countertop. Natural light illuminates the room, creating a warm and open atmosphere.

Apartment in Sheffield

Hideaway with Spectacular Berkshire Views

Great locationFriendly hostGreat stay

4.99 out of 5 average rating, 235 reviews

A living room is displayed, featuring a comfortable blue couch adorned with patterned pillows. Three framed landscape images are mounted on the wall above a wooden coffee table. Natural light enters through a window with sheer curtains, illuminating a cozy reading nook in the background.

Apartment in Northampton

Cozy Haven: Convenience & Charm

Great locationQuiet surroundingsWell-equipped facilities

Condo rentals with outdoor seating

Condo in Litchfield County

A well-lit bedroom features a spacious bed covered in neutral bedding. A wooden dresser and a small nightstand with a lamp are positioned beside the bed. Natural light streams through a round window highlighting the warm wood floors.

4.93 out of 5 average rating, 30 reviews

Meadow View

Great locationExcellent serviceWell-equipped facilities

Condo in Hartford

4.79 out of 5 average rating, 24 reviews

Spacious Condo • Quick Drive to Everything

Great locationCleanGreat stay

4.94 out of 5 average rating, 71 reviews

A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.

Condo in Hancock

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Great locationGreat stayClean

5 out of 5 average rating, 10 reviews

Condo in Downtown Albany

Historic Gem, Fireplace,2BR/2BA,Capitol District

Friendly hostExcellent serviceStylish design

4.91 out of 5 average rating, 46 reviews

A dining area features a light-colored table with four wooden chairs, complemented by a decorative fruit bowl. Exposed brick walls add character, while soft lighting from nearby lamps creates a bright and inviting atmosphere. A comfortable living space is also visible in the background.

Condo in Lenox

Spacious 3 bedroom apt in Lenox historic downtown

Great locationFriendly hostExcellent service

4.9 out of 5 average rating, 51 reviews

A spacious light blue deck is shown, furnished with a small table and two white chairs. The surrounding area features greenery and a distant view of rolling hills, providing a serene outdoor space for relaxation.

Condo in Shelburne Falls

Flowers & Falls Spot House

Great locationGreat stayFriendly host

A bright and spacious bedroom features a large bed with soft bedding, complemented by two bedside lamps. A wooden bench sits at the foot of the bed, and a dedicated work desk is positioned near a window, allowing natural light to fill the room.

Condo in Simsbury

Luxury furnished condo. Attached garage. Fireplace