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Vacation rentals with outdoor seating in Lenox

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Top-rated outdoor seating rentals in Lenox

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

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

4.99 out of 5 average rating, 334 reviews

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.

A striped hammock is suspended between trees, set against a backdrop of lush greenery and the cottage above. The property is surrounded by stones and ferns, creating a serene natural environment that invites relaxation.

Cottage in Becket

4.94 out of 5 average rating, 214 reviews

Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D

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 • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • 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

A modern living area features large windows allowing natural light to fill the space. A cozy sofa and a comfortable chair invite relaxation, while a country-style table accommodates dining or work. The decor is enhanced by a colorful area rug and minimalistic furnishings.

Guest suite in Richmond

4.93 out of 5 average rating, 184 reviews

Tanglewood/Private Ranch/Kid&Pet Friendly/Horses

Pet-Friendly, Child-Friendly Getaway! Modern suite with full kitchen on private horse ranch. Wake to horses in the fields, hiking, breakfast on your patio. Perfect location for individuals, couples, families animal lovers. Near all ski areas (Jiminy Peak/Catamount/Bousquet /Butternut), shopping, museums (Norman Rockwell/Mass MoCA) wine tasting (Balderdash Cellars, Hilltop Orchards) Tanglewood, Jacobs Pillow, Miraval, Kripalu, Canyon Ranch. Trail ride lessons /Horse activities available by appt!

A whimsical tower with a conical roof is framed by lush greenery. A stone path leads to an intricately carved wooden door, surrounded by seasonal flowers. Natural stone and rustic wood elements enhance the enchanting garden setting.

Tiny home in Tyringham

4.97 out of 5 average rating, 365 reviews

Enchanted Tiny Tower nestled in the Berkshires

Whimsical and romantic tower on the Santarella Estate in Tyringham, MA in the heart of the Berkshires. Live out your fairytale in this two-story unique, tiny home. First floor offers 3 rooms in one with kitchenette, sitting area, and dining room looking out on to the babbling brook. Upper bedchamber with canopied bed provides amazing views of sky and trees through massive, mill windows. Perfect destination for a relaxing getaway or special stay while exploring all the Berkshires has to offer.

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

4.88 out of 5 average rating, 218 reviews

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!

Lush, colorful flowers surround the entrance of the cottage, adding a vibrant touch to the exterior. A combination of greenery and blooms creates a welcoming atmosphere. The cottage features large windows, allowing for ample natural light and offering views of the blooming landscape.

4.93 out of 5 average rating, 232 reviews

Heart of Lenox Walk to Town Cozy Cottage!

The cottage is a 2-minute walk to Church St., right in the heart of Lenox. Kennedy Park (1.5 miles) is a short stroll away for great hiking & biking, while multiple 5-star restaurants are all within a few minute walk. Tanglewood (2 miles), Kripalu (3 miles), Shakespeare & Co. (1 mile), Berkshire Theatre Festival & the Norman Rockwell Museum (7 miles), Butternut, Jiminy Peak (15 miles) & Bousquet (5 miles) ski area, Mahaiwe Performing Arts Center & Jacob's Pillow (14 miles) are all close by!

The living room features a wood stove, providing a focal point for warmth. A large sectional sofa is positioned for comfort, alongside a wooden rocking chair. Natural light filters through sheer curtains, illuminating the space, which is also equipped with air conditioning and a modern floor lamp.

4.9 out of 5 average rating, 258 reviews

Cozy Berkshires Cottage

Stay in a cozy, newly remodeled Berkshires 1920's cottage! We've added bedrooms and a bathroom with a soaking tub upstairs, expanded the first floor bathroom and added a laundry room. The cottage is set back from the main road, easily accessible yet private. -Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. -Ideal for couples, adventurers, business travelers, and furry friends (pets). -Note: Stairs to the 2nd floor are steep: guests are responsible for child safety.

A sunlit living area is furnished with a spacious sectional sofa and a round coffee table atop a patterned area rug. The hardwood floors and natural light from the multiple windows enhance the room's inviting feel, complemented by a decorative fireplace and wall art.

4.88 out of 5 average rating, 161 reviews

Spacious 4-Bedroom Colonial Gem in Downtown Lenox

Spacious 4-Bedroom Retreat in Lenox, MA Experience your perfect getaway in this beautifully renovated home in Lenox, MA. This charming 4-bedroom, 3-bathroom retreat offers 2,089 sq. ft. of space and is designed for a comfortable stay. The deck, BBQ grill, and cozy seating make for memorable gatherings. The Wi-Fi is fast for all your streaming needs, and there are 2 Wi-Fi HDTVs. Lenox, MA, is a picturesque town in the heart of the Berkshires. Book your stay today!

Top guest favorite

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

4.99 out of 5 average rating, 223 reviews

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.

Top guest favorite

An entryway features a grey console table with glass-front cabinets, topped by a table lamp and a potted plant. A round mirror hangs above the table, while a doorway leads into the home, revealing glimpses of the kitchen and hallway beyond.

Home in Stockbridge

4.95 out of 5 average rating, 132 reviews

Sun-filled, Charming Stockbridge Classic- In Town!

Beautiful remodel on a classic old, well-appointed New England house located in the middle of town on a dead-end road leading to hiking trails for Laura's Tower. A quick walk to Downtown Stockbridge, Red Lion Inn, gas station, cafes, markets, shops... everything you need. A park sits directly across the street with open acreage, swings, sandbox, skate park. Parking available on site. Located within minutes of four season activities- happy to make recommendations!

The exterior of the Granary is highlighted, featuring a mix of red barn siding and natural stone. The two upper windows allow natural light inside, while a mint green double door adds a pop of color. Lush greenery and colorful flowers surround the entrance.

Guesthouse in Lenox

4.93 out of 5 average rating, 376 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

A cottage entrance is framed by lush greenery, with a stone pathway guiding guests to a welcoming front porch. The wooden door features a round window, and large windows on either side allow natural light to illuminate the space, surrounded by vibrant flora.

4.96 out of 5 average rating, 179 reviews

Lenox - Walk to Town - Berkshire Home

Come, enjoy the Berkshires! This cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a large front yard and beautiful backyard for grilling. Explore the best of Lenox and the Berkshires activities and fare! Sitting in this cottage surrounded by forest, you really feel like you are in the shire!

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Popular amenities for Lenox outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

The exterior of a two-story home features a combination of dark wooden and white siding. A well-maintained garden with colorful flowers surrounds the house, complementing the lush greenery of the yard. Large windows reflect the natural light filtering through the trees.

5 out of 5 average rating, 25 reviews

Cliffwood Cottage

A spacious living room is presented, featuring a large, dark sectional couch with various cushions. A 60-inch 4K TV is positioned on a low media console, opposite the couch. Natural light filters through sheer curtains into the room, complemented by a soft area rug and a potted plant.

4.87 out of 5 average rating, 46 reviews

Spacious & Family-Ready Home w/ Fenced Yard in Lee

A charming two-story house is set against a snowy landscape, surrounded by tall trees. Soft golden light is seen emanating from one window, contrasting with the cool tones of the winter scene. A wooden fence borders the property, partially covered by fresh snow.

4.96 out of 5 average rating, 48 reviews

Lenox Farmhouse, three blocks to village!

A blue front door with an oval glass inset stands prominently against a white wooden facade. A small porch is visible, featuring a wooden bench and a gray chair. Fallen leaves are scattered across the gray decking.

Home in Richmond

4.94 out of 5 average rating, 18 reviews

Sunshine Cottage

The exterior of a transformed church features a pointed steeple and a central double door framed by a decorative arch. Stained-glass windows are visible, adding a historic charm against the dark wood siding. The surrounding area is lined with trees, hinting at the serene natural setting.

Home in Great Barrington

5 out of 5 average rating, 3 reviews

Berkshires Black Abbey

Top guest favorite

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

4.95 out of 5 average rating, 175 reviews

Cantabile life in the Berkshires

A serene view of a winding driveway surrounded by vibrant perennial gardens. Colorful flowers grow abundantly along the path, leading to a scenic landscape of rolling hills and distant mountains under a partly cloudy sky.

Home in Pittsfield

4.98 out of 5 average rating, 125 reviews

Hidden Oasis in the Mountains by Evergreen Home

Top guest favorite

A warm fire burns within a stone fire pit, with flames flickering against the evening sky. The serene lake reflects the fading light, while a wooden dock is visible in the distance, surrounded by tall reeds and lush greenery.

5 out of 5 average rating, 27 reviews

Lakefront Retreat -Private Dock,creek,and Fire pit

Apartment rentals with outdoor seating

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

4.97 out of 5 average rating, 272 reviews

Sunny, light filled loft in 1873 Colonial

An airy interior showcases exposed wooden beams and a blend of modern and rustic decor. A kitchen counter with stools is positioned towards the left, complemented by a dining table with chairs in the center. A cozy bedroom is visible through the doorway on the right.

Apartment in Philmont

4.9 out of 5 average rating, 119 reviews

Beautiful space in the heart of Philmont

Top guest favorite

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.

Apartment in East Chatham

4.95 out of 5 average rating, 122 reviews

Bennett Abode

A spacious room features a plush king-sized bed centered on a decorative area rug. Dark-colored walls provide contrast to the light wooden flooring. A functional desk and chair are positioned by the window, with a small kitchenette area visible. A bathroom door is seen in the background.

Apartment in Great Barrington

4.9 out of 5 average rating, 135 reviews

King Bed|Wi-Fi|2m Ski Resort

Top guest favorite

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

4.95 out of 5 average rating, 271 reviews

Sunny carriage house apartment

Top guest favorite

A cozy seating area features a large, woven hanging chair with a white cushion and a bright green accent pillow. A textured pouf and a small side table complement the space, which is surrounded by large windows offering views of the mountains and natural light.

Apartment in Freehold

5 out of 5 average rating, 306 reviews

Mountain View Retreat~Sunny Hill Golf / Skiing

Top guest favorite

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

4.97 out of 5 average rating, 566 reviews

Steps to MoCA: 2bd + SAUNA!

Top guest favorite

A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.

Apartment in Coxsackie

5 out of 5 average rating, 116 reviews

Hudson River Beach House

Condo rentals with outdoor seating

A multi-level chalet-style building features a blend of wood and stone exteriors. Large windows enhance natural light, and several balconies overlook a lush green landscape. A wooden bridge leads across a small waterway, connecting seamlessly to the surrounding nature.

Condo in Hunter

4.86 out of 5 average rating, 138 reviews

Trailside At Hunter-Phase II-Hunter NY

A snowy landscape showcases the mountain in the background with ski trails visible. The foreground features a winter scene with snow-covered ground and trees. A building is partially visible on the left, adding to the serene atmosphere.

4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

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.

4.94 out of 5 average rating, 36 reviews

Spacious 3 bedroom apt in Lenox historic downtown

Top guest favorite

A modern living room corner features a brown leather recliner with high backrest beside a window. A small table holds a potted plant, while a wood stack is positioned against the wall for a rustic touch. Natural light filters through brown curtains.

4.99 out of 5 average rating, 120 reviews

Summer Dream! The Handle Lodge at Snowtree Condos

Top guest favorite

The exterior of the studio is framed by lush greenery and well-maintained landscaping. Large glass doors provide entrance to the studio, while a hammock is visible on the patio above. The peaceful outdoor setting offers ample grass space shaded by trees.

Condo in Northampton

4.94 out of 5 average rating, 101 reviews

Cozy Studio with patio, 1.2 mi from downtown

Icicles hang from a structure in the foreground, with a view of snow-covered ski slopes illuminated by soft lights in the distance. The landscape is blanketed in fresh snow, creating a serene winter atmosphere.

Condo in Hancock

5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Top guest favorite

The exterior showcases a two-story condo surrounded by greenery. A pathway lined with gravel leads to the entrance. Flowering plants and shrubs are visible along the pathway, and a lamp post adds a lighted accent. The condo features a mix of dark and muted colors with a welcoming porch.

4.92 out of 5 average rating, 125 reviews

3 Story Condo - 5 Minutes to Mount Snow!

A spacious living area features large windows offering mountain views. A beige couch with textured cushions sits on a plush carpet. A wooden coffee table is positioned in front of the couch, complemented by a decorative wall hanging. A guitar rests on the floor beside a low bench.

Condo in East Jewett

4.97 out of 5 average rating, 126 reviews

MountainViewBrightCondo10MinToColgateLakePool

Quick stats about vacation rentals with outdoor seating in Lenox

Total rentals
110 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
4.9K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool

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