Holiday rentals with outdoor seating in Weston

4.96 out of 5 average rating, 108 reviews

The cabin's exterior showcases a sturdy log design with a grey roof and inviting wrap-around porch. Flowering planters are placed on either side of the door, and two rockers are positioned for outdoor relaxation, surrounded by landscaped gravel.

Cabin in Andover

Little Cabin on the Ridge

Classic Vermont cabin.This cozy home is perfect for singles, couples and families.The well-designed space offers sleeping for 4 in two bedrooms and an open loft space. Wrap around porch has 4 rockers for taking in the mountain air, coffee or tea, or reading in a cozy quilt. Fiber optic wifi 1000 mbps.Very efficient forced hot air heating and Central Air cooling.Peaceful, quiet,relaxing, great place to unwind with all kinds of activities nearby. due to health and safety concerns no animals please

4.99 out of 5 average rating, 144 reviews

An outdoor tub is situated on a wooden deck, surrounded by vibrant autumn foliage. A red faucet provides a natural flow of water, while a small bowl of floating objects rests nearby. In the background, a glimpse of a serene lake can be seen through the trees.

Cabin in Stoddard

Boulder House - Extraordinary Luxury in the Woods!

From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

4.99 out of 5 average rating, 148 reviews

A spacious living area features a central stone fireplace, surrounded by cozy seating. Large windows frame scenic views of the trees outside, filling the space with natural light. The rustic wooden beams and walls add warmth, while the open layout connects to the kitchen and loft above.

Barn in Andover

Fat Cat Barn - Close Okemo & Magic, Vermont

Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

4.88 out of 5 average rating, 154 reviews

A charming treehouse is nestled in a snowy landscape, elevated on stilts with a wraparound deck. Soft white lights illuminate the exterior, while snow gently falls around it. A wooden staircase leads up to the entrance, highlighting the inviting ambiance.

Treehouse in Londonderry

Riverbed Treehouse @hot tub & a new sauna & views!

The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

4.97 out of 5 average rating, 108 reviews

A spacious lawn is shown, featuring two buildings. One is a charming cottage with large glass doors, while the other is a main house with a traditional exterior. The ground is covered with fallen leaves, and trees line the background.

Cottage in Weston

Charming Mountain Cottage **NO CLEANING FEE**

Enjoy a charming cottage on the side of a hill in beautiful Weston, Vermont. You'll have the entire building to yourself (it's a stand-alone structure) to come and go as you please. My goal is to provide a five-star experience for five-star guests. I think little details like Ralph Lauren bath sheets, freshly-pressed bed linens, and duvet covers that are laundered between each guest make a difference. If you agree, you're probably the type of guest I'd enjoy hosting! Motorcycle friendly!!

4.99 out of 5 average rating, 354 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, 211 reviews

The rustic cabin sits amidst a lush green landscape, framed by towering trees. The stone chimney adds character, while the two separate structures showcase a combination of wood siding and modern roofing. Clear blue skies create a serene backdrop for the natural beauty.

Cabin in Landgrove

The Owl’s Nest in Landgrove

Our recently renovated cabin is the perfect escape during any season! Located within minutes of Bromley, Magic, and Stratton, Wild Wings, and Viking. Also nestled in an amazing network of hiking, biking and ski trails. Guests will never be more than a few minutes away from outdoor adventure. With two bedrooms and one bonus loft, guests can enjoy the comforts of our cozy cabin, including a full kitchen, bathroom, outdoor shower, HOT TUB, fire pit, WiFi and FREE EV CHARGING. @owlsnestvt

4.87 out of 5 average rating, 160 reviews

An A-frame cabin is nestled among trees with autumn leaves in vibrant shades. A large deck extends from the cabin, featuring a hot tub and outdoor dining area. A barrel sauna is positioned nearby, completing the inviting outdoor space.

Cabin in Mount Holly

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.

4.95 out of 5 average rating, 102 reviews

A modern cabin is situated in a snowy landscape, surrounded by tall evergreen trees. Large windows reflect the falling snow, creating a serene atmosphere. A snow-covered rock ledge lines the front, enhancing the cabin's rustic charm against the winter backdrop.

Cabin in Cavendish

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board

Escape in a beautiful light-filled upscale cabin deep in the woods at Sugar Maple Mountain Retreat. Relax at the end of the day in our hot tub which is shared between our 3 cabins. Steps away from two picturesque lakes, enjoy complimentary seasonal use of our kayaks, paddle boards and snow shoes. Go fishing, biking, hike country roads or trails on the 1275 acres of surrounding preserved land. In winter hop on the VAST trail nearby. 4 WD Required Dec 1- April 15th

4.98 out of 5 average rating, 163 reviews

A charming home is shown, featuring a combination of wood and glass elements. The property is surrounded by green lawn and seasonal foliage. Rolling pasture views are visible in the background, lending a serene and open feel to the setting.

Home in Peru

Serene & Pristine Vermont Home

Perfect for a staycation, as a work-from-home alternative, or for family vacations. Situated on the edge of picturesque 120 acre New Spring Farm that borders the Green Mountain National Forest, is this up to date charming home awaiting your visit. With brilliant natural light and rolling pasture views, the quiet dead end dirt road provides privacy, while still being only a mile from J.J. Hapgood general store and centrally located to multiple towns and ski areas.

4.98 out of 5 average rating, 753 reviews

An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.

Cottage in Shaftsbury

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Superhost

A modern cabin features a contrasting black exterior and wooden accents, nestled among lush trees. A wide deck with railing leads to the entrance, offering a welcoming space to enjoy the surrounding nature. Large windows provide ample natural light and views of the forest.

Tiny home in Athens

4.84 out of 5 average rating, 170 reviews

LUXE Forest Retreat

Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

Popular amenities for outdoor seating rentals in Weston

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.98 out of 5 average rating, 227 reviews

A comfortable sofa adorned with decorative pillows and a cozy throw stands before a wall of glass doors. The view of Lake Sunapee stretches beyond, framed by trees and vibrant outdoor furniture on the deck.

Home in Sunapee

@SunapeeSeasons—Across from Dewey Beach, Lake View

4.99 out of 5 average rating, 334 reviews

A white farmhouse-style structure is set on a lush green hill, surrounded by a clear blue sky. The building features a gabled roof, multiple windows, and a small cupola. A neat lawn frames the house, emphasizing its inviting exterior.

Home in Bennington

Cozy Modern Sugar House with spectacular views.

5 out of 5 average rating, 113 reviews

A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.

Home in Bennington

The Vermont Farmhouse|Hiking|Dog Trails|Village

4.99 out of 5 average rating, 151 reviews

An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.

Home in Londonderry

Modern 3-bedroom A-frame in Londonderry w/ Pond

4.95 out of 5 average rating, 171 reviews

A cozy fire pit is surrounded by stone, situated in the foreground of a spacious lawn. In the background, a modern chalet features large windows and a combination of wood and stone siding, framed by colorful autumn foliage.

Home in Winhall

Summit View Ski and Golf Retreat w/hot tub & Sauna

4.95 out of 5 average rating, 329 reviews

Home in Clarendon

Killington Retreat | Deck-Fire Pit-Mountain Views!

4.98 out of 5 average rating, 127 reviews

Home in Windsor

Stylish Vermont Cabin | Views · Trails · Luxe

4.99 out of 5 average rating, 283 reviews

A charming red barn with a pitched roof is prominently displayed against a backdrop of rolling hills and cloudy skies. A welcoming sign featuring a cow stands at the entrance next to a gravel drive, inviting guests to explore the countryside.

Home in Mount Tabor

Cow Barn Lodge

Apartment rentals with outdoor seating

4.93 out of 5 average rating, 164 reviews

A welcoming storefront features a wooden sign for Simon Pearce, accompanied by colorful pumpkins and vibrant yellow mums. The gray building showcases a green roof and large windows, with outdoor seating available on the patio. A blue sky with scattered clouds serves as the backdrop.

Flat in Chester

Lovely 2 Bedroom Apartment w/deck & pond view

Flat in Marlboro Township

A gently sloping lawn leads up to the light-colored building, framed by lush gardens and vibrant greenery. A pair of purple Adirondack chairs sits invitingly on the grass, offering a serene spot to enjoy the surrounding landscape.

4.93 out of 5 average rating, 294 reviews

Shakespeare’s Folly Side Farm and AirBnB.

4.93 out of 5 average rating, 127 reviews

The exterior of a red wooden house is showcased, surrounded by lush green grass and trees. A neatly trimmed garden features colorful flowers, while a small shed is visible in the background. Pebbled pathways provide access to the home's entrance.

Flat in Mount Tabor

Vermont Ski / Okemo / Killington / Pico / Stratton / Bromley

4.95 out of 5 average rating, 260 reviews

A comfortable white sofa with decorative pillows is positioned against a light wall. A small, light-colored side table holds a potted plant. Natural light streams in through a nearby window, illuminating the wooden floor and a blue woven rug beneath.

Flat in Dummerston

HeART Barn Retreat

5 out of 5 average rating, 113 reviews

A cozy seating area is presented, featuring a patterned rug beneath a wooden coffee table. A sofa with light-colored cushions and decorative pillows is accompanied by a lamp providing warm light. A chest of drawers and a framed artwork add character to the inviting space.

Flat in Wallingford

49 River Street

4.95 out of 5 average rating, 357 reviews

An open living space is captured, featuring a comfortable couch, a colorful chair, and a round coffee table. Natural light brightens the room, highlighting a kitchenette area and coordinating furnishings across the suite. High ceilings contribute to an airy atmosphere, creating a welcoming environment.

Flat in Clarendon

Dog heavenly! Private, beautiful and relaxing.

4.96 out of 5 average rating, 121 reviews

A modern kitchen features sleek white cabinetry and open shelving displaying glassware and kitchen essentials. A wooden dining table with black chairs provides a gathering space. Stainless steel appliances, including an oven and microwave, complement the stylish design, while a fresh plant adds a touch of greenery.

Flat in Ludlow

Peaceful Ludlow Base 5 minutes to Okemo

4.94 out of 5 average rating, 382 reviews

A two-story, white wooden house is surrounded by lush greenery and shrubs. A porch with a small seating area is visible, along with an air conditioning unit installed on the upper level's front wall. The bright sky and soft clouds provide a picturesque backdrop.

Flat in Poultney

Cozy Poultney Village Apartment

Apartment rentals with outdoor seating

4.99 out of 5 average rating, 142 reviews

The dining area features a large wooden table surrounded by six stools. A metal-framed desk and chair are present nearby, along with a coffee maker and additional kitchen appliances. Light wood flooring complements the neutral walls, creating a spacious and functional environment.

Apartment in Ludlow

Main St Escape | Explore Downtown Ludlow

A view from the balcony showcases the surrounding landscape, highlighting green hills and clear blue skies. Two adjoining buildings are visible, featuring sloped roofs and a variety of architectural styles. The area appears tranquil, with open spaces and scattered trees enhancing the natural scenery.

4.95 out of 5 average rating, 202 reviews

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

A cozy living room features a dark leather sofa adorned with decorative pillows. Above the couch, three framed nature-themed art pieces display serene mountain landscapes. A dog rests comfortably on the carpet, with soft lighting from two side lamps enhancing the peaceful ambiance.

4.95 out of 5 average rating, 167 reviews

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

Aerial view of the ski resort highlighting the surrounding Green Mountains. The image captures the condo's sloped roof and multiple skylights, with ski trails visible on the mountain slope. Lush greenery fills the valley, creating a scenic backdrop.

4.79 out of 5 average rating, 262 reviews

Cozy Studio for 4 - Walk to Mountain w/Balcony

4.99 out of 5 average rating, 134 reviews

A spacious living area features a large sectional sofa adorned with cozy throw pillows, complemented by a textured area rug. Natural light pours in through expansive windows, enhancing the inviting atmosphere. A side table and a plush armchair add to the comfortable seating options.

Apartment in Dover

Winter Dream! The Handle Lodge at Snowtree Condos

A cozy living area is visible, featuring a dining table surrounded by bright yellow chairs. A fireplace is seen, enhancing the space, while a large bear-themed wall mural adds a touch of nature. Natural light floods in from the nearby window.

4.93 out of 5 average rating, 215 reviews

CozyCub- Location, Ski Off/Shuttle On!

4.95 out of 5 average rating, 117 reviews

The exterior of the condominium building is showcased, featuring three levels with large windows that allow natural light in. A central staircase leads to the entrance, flanked by green grass and small shrubs, creating a welcoming appearance.

Apartment in Stratton

Great 2 bedroom condo at Stratton Mountain

A spacious living room features a real wood fireplace with a modern hearth, surrounded by a cozy seating arrangement. A flat-screen television is mounted above the fireplace. Large windows provide natural light and a view of the outdoor balcony, enhancing the inviting atmosphere.