Holiday rentals with outdoor seating in Lee

4.95 out of 5 average rating, 468 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, 307 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. $29. pet fee = approved Pet Agreement.

4.97 out of 5 average rating, 395 reviews

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

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.

4.99 out of 5 average rating, 372 reviews

Tiny home in Wilmington

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

4.99 out of 5 average rating, 114 reviews

A modern kitchen is equipped with stainless steel appliances and wooden cabinetry, complemented by light hardwood flooring. A rustic table with a fruit bowl is surrounded by four wooden chairs. A glass door provides access to the outdoor deck, allowing natural light to fill the space.

Cottage in Lee

Perfect Holiday Home Renovated & Fully Equipped

Welcome to Prospect Place! Our charming renovated home is set upon a hilltop overlooking downtown Lee, "The Gateway to the Berkshires." The house is in the heart of the Berkshires and central to just about everything. It is a a short drive to Tanglewood, the Berkshire Theater Festival, Jacobs Pillow and the Berkshire Outlet Mall. Golf, tennis, skiing, swimming, and spas are just minutes away. It is a perfect spot for relaxation, culture, sports, a girls weekend, and family gatherings.

4.99 out of 5 average rating, 127 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.

Guesthouse in Stockbridge

A modern, renovated barn is set against a backdrop of lush greenery. Two brightly colored lounge chairs and a reclining chair are positioned on the grassy area, inviting relaxation. Large windows reflect the surrounding trees, emphasizing the tranquil outdoor setting.

4.9 out of 5 average rating, 152 reviews

Modern barn in the heart of the Berkshires

Modern, renovated dairy barn in the heart of the Berkshires. Located on 3.5 acres with beautiful views and close to everything. 1.5 miles to Main St Stockbridge/Red Lion Inn, 5 minutes to Tanglewood, 5 minutes to the Stockbridge Bowl and beautiful hiking trails, under 10 minutes to Lenox . This is the perfect base for exploring the Berkshires or a great getaway for relaxing and enjoying nature. Family and pet friendly! *Please read Interaction with Guests section before booking*

4.88 out of 5 average rating, 242 reviews

Cabin in Stockbridge

Hip Stockbridge Cabin - A stroll to the lake

Welcome to our stylish glamping cabin! Relax in the spacious yard & sunny deck. Cozy fieldstone fireplace, vaulted ceilings & skylights. The cottage features gorgeous pine wood & fantastic interior design. Unwind in the reading nook, master bedroom with skylights, or put on your favorite vinyl. Kids will adore the sleeping loft. Just a 9-minute walk or 2-minute drive to the public beach (the beautiful Stockbridge Bowl). BBQ grill, outdoor fire pit . Tanglewood is just minutes away.

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.

Apartment in Great Barrington

A modern bedroom features a spacious bed dressed in crisp white linens, flanked by two stylish stools. The dark green wall is adorned with sleek light fixtures and framed art, creating a balanced and inviting aesthetic.

4.91 out of 5 average rating, 110 reviews

King Bed|Wi-Fi|2m Ski Resort|Berkshires

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv

4.99 out of 5 average rating, 303 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.

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, 337 reviews

Artist Cottage

Artsy vintage cottage with a private lodge in a quiet Berkshire neighborhood. Backyard opens to woods with trails nearby. Enjoy fireplaces and hot tub in winter, waterfall and outdoor shower in summer. Upstairs queen ensuite with bathroom and soaking tub; downstairs retro kitchen, living room, and full bath with shower. Lodge offers comfy seating, farm table, and big-screen TV. High-speed internet, Prime & Spectrum TV.

Popular amenities for Lee outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.93 out of 5 average rating, 130 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

4.98 out of 5 average rating, 125 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

4.99 out of 5 average rating, 128 reviews

A serene bedroom is presented with a spacious bed adorned with soft linens and a cozy throw. Two bedside tables hold elegant lamps, and natural light floods the room through large windows. A decorative wreath hangs above the headboard, enhancing the tranquil ambiance.

Home in Sheffield

Belle Meade

4.96 out of 5 average rating, 387 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

4.99 out of 5 average rating, 123 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!)

4.98 out of 5 average rating, 186 reviews

A serene landscape is captured, featuring a tall tree with budding leaves beside a rustic barn. Mist gently envelops the grassy area, creating a tranquil atmosphere as light filters through the trees in the background.

Home in Saugerties

The Stone House

4.97 out of 5 average rating, 115 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

4.99 out of 5 average rating, 241 reviews

A cozy living room features a brown sofa positioned centrally, paired with an ottoman. Striped armchairs flank the space, with two lamps providing soft illumination. Warm wood paneling and large windows contribute to a welcoming ambiance, complemented by a decorative area rug underneath.

Home in Colebrook

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 296 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

Apartment in Great Barrington

A cozy living room features a light sofa and two armchairs flanking a wooden coffee table. A decorative rug with intricate patterns lies beneath. Natural light filters through multiple bay windows, highlighting the serene and vintage-inspired decor.

5 out of 5 average rating, 139 reviews

Walk Everywhere! | Relax in Easy Elegance!

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, 166 reviews

Bennett Abode

4.99 out of 5 average rating, 153 reviews

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

Hudson River Beach House

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, 366 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

4.96 out of 5 average rating, 124 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.

4.99 out of 5 average rating, 243 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

4.99 out of 5 average rating, 438 reviews

A spacious sleeping area features a California king bed with light bedding. Decorative pillows add a soft touch. A stone wall and floral artwork enhance the room's character. Soft lighting from unique lamps provides a warm glow, complemented by a cozy seating bench at the foot of the bed.

Apartment in Simsbury

Ensign House Room

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

Condo in Hartford

4.78 out of 5 average rating, 27 reviews

Spacious Condo • Quick Drive to Everything

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

4.91 out of 5 average rating, 47 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

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

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