Holiday rentals with outdoor seating in Pittsfield

5 out of 5 average rating, 176 reviews

A cozy living area showcases a comfortable sofa adorned with patterned cushions and a soft throw. A rustic coffee table sits in front, complemented by stylish armchairs. Natural light filters through large windows, illuminating the modern kitchen with dark cabinetry in the background.

Tiny home in Fairlee

Private, 1 bedroom boutique tiny home

This boutique tiny home is situated in the picturesque Upper Valley of Vermont. The nearly 50 acres of private land is equal parts woods and water. You will wake to the mooing of dairy cows. Have your coffee on the porch while watching birds dive for their breakfast on the pond. Inside you will find every modern amenity. A fully appointed chef's kitchen. A living area filled with comfy furnishings and a cozy fireplace. Upstairs is a queen bedroom with an ensuite double showered bathroom. Heaven!

4.9 out of 5 average rating, 105 reviews

A charming treehouse is perched among vibrant autumn foliage, surrounded by trees displaying shades of yellow and red. The wooden structure features a red roof and a spacious deck that offers a scenic view, harmonizing with the natural hillside landscape.

Treehouse in Warren

The Birch Perch! Treehouse with spa and fire pit!

Romantic Honeymoon or fun family fantasy come true this treehouse has it all! Built by The DYI Network Treehouse Guys! Every detail custom crafted in this home in the tree tops makes your ultimate Vermont experience. All just 8 minutes to the lifts at Sugarbush. Kitchenette, cast iron stove, clawfoot tub, washer/dryer, AC, & outdoor shower all encased in a whimsical perch near skiing, waterfalls, biking and hiking. Incredible hillside views from your private deck! Romantic Hot tub in the trees!

Guest suite in Stockbridge

5 out of 5 average rating, 115 reviews

Studio Suite with Vermont Style & Amazing Views

Central to Killington, Pico & Sugarbush Ski Areas. Breathtaking views. Features all Vermont has to offer in any season - Golf, Downhill & X-country Skiing, nearby VAST trails, Snowshoeing, Hiking, Trail & Road Biking. Unit is en suite w/sitting area, dining table/desk, kitchenette (no stove). Shower and toilet with ADA bars. Handicap accessible. Large closet, dresser. Streaming TV/DVD/VHS, selection of games, discs and tapes. 2 entrances - public and private. Stone patio and fire pit. Quiet.

4.96 out of 5 average rating, 579 reviews

The uniquely shaped house, adorned with shingles, is surrounded by lush greenery. Large windows reflect the vibrant foliage, allowing natural light to illuminate the structure. The natural stone wall complements the rustic aesthetic, creating a harmonious blend with the wooded landscape.

Home in Fairlee

Cozy Bow House Perched in Trees w/ Hot Tub & View

The cozy Bow House is perched up above a lovely valley and boasts large south facing windows, a unique bowed loft and a warm, inviting space to relax. Up a charming dirt road past Brushwood & Fairlee Forests with hiking, biking and ATV trails nearby. Lake Fairlee is a scenic 10 min drive; 15 min to Lake Morey & I-91 and 30 min to Dartmouth College. Enjoy the glow of the rising sun and beautiful views above the fog, unwind in the hot tub surrounded by the magical woods and wildlife of Vermont.

4.85 out of 5 average rating, 193 reviews

An A-frame chalet features a sloped metal roof and wooden exterior, surrounded by verdant greenery. A welcoming wooden deck with stairs leads to the entrance, inviting guests to enjoy the natural setting. Large windows allow for sunlight to illuminate the space.

Chalet in Stockbridge

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

5 out of 5 average rating, 155 reviews

A lush, green landscape is framed by trees and gently sloping hills. The manicured lawn leads to a quaint white home in the distance, surrounded by vibrant foliage under a partly cloudy sky.

Guest house in Corinth

The Guest House at Chandlery Farm

This classic Vermont farm estate has everything that description implies: end-of-the-road privacy with breathtaking views, where the only sound is the wind rustling through the leaves. The manicured gardens, stone walls and quaint but luxurious home seem plucked from classic American folklore. Guests can drink their morning coffee while soaking in views of rolling pastures and forested hills, and spend their days exploring the property's trails, and the beautiful towns and countryside nearby.

4.98 out of 5 average rating, 186 reviews

Cabin in Pittsfield

Tiny Vermont Cabin!

Newly built tiny cabin in the woods of Vermont! Perfect for a quiet get away and close by outdoor fun! Killington and Pico Mountain is 15 minutes away! Sugarbush is 50 minute drive. Coming to Pittsfield for a wedding? Riverside Farm is only .7 of a mile down the road! Winter: MUST have AWD/4x4 for winter access on dirt road and driveway. Snow tires recommend. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the beauty Vermont has to offer!

4.93 out of 5 average rating, 122 reviews

A spacious outdoor deck features a mix of seating, including lounge chairs and a table set for two. String lights are elegantly draped above, providing a warm glow. Surrounding trees add to the natural setting, enhancing the peaceful atmosphere.

Cabin in Stockbridge

1958 Classic "Hunting Cabin" w/ Breathtaking Views

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

4.99 out of 5 average rating, 305 reviews

The kitchen area features a large island with seating and modern appliances. Natural wood paneling complements the high cathedral ceiling. Glass doors open to a scenic view of the surrounding hills, providing ample natural light and a connection to the outdoors.

Barn in Woodstock

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". A lofted space on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony. For more go to @theloft.vt

4.94 out of 5 average rating, 272 reviews

A charming red house is set against a lush green backdrop. Large windows provide natural light and views of the surrounding trees. A wooden deck is featured at the front, leading to a beautifully maintained lawn, inviting outdoor activities.

Cabin in Hancock

Hancock hideaway

Skiing, snow biking 10 minutes away at Middlebury Snow Bowl and Rikert crosscountry. Sugarbush and Killington half hour drive. Snowshoeing and hiking right behind house in the Green Mountain National Forest. Easy drive to river swimming holes and lakes. Excellent restaurants in Waitsfield and Middlebury - about half hour. Good restaurant, cafe, small grocery store, in Rochester, 4 miles. Great location, beautiful views, lovely little house, totally private, romantic.

4.87 out of 5 average rating, 163 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.

4.99 out of 5 average rating, 314 reviews

A modern house with wooden exterior is shown from an elevated perspective, surrounded by autumn foliage. A hot tub is positioned on a spacious deck, which includes a seating area with four chairs and a small table. Scenic mountain views and vibrant trees enhance the natural setting.

Tiny home in Warren

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

Popular amenities for outdoor seating rentals in Pittsfield

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.98 out of 5 average rating, 151 reviews

A bright living area is illuminated by large picture windows showcasing panoramic views of rolling green hills. Comfortable seating arrangements include a sofa and armchair, positioned around a wooden coffee table. A cozy fireplace and a projector screen are visible, enhancing the inviting space.

Home in Pomfret

Private Oasis Under 10 Mins from Woodstock

4.89 out of 5 average rating, 121 reviews

Home in Killington

Steps to Golf and Mountain Biking

4.97 out of 5 average rating, 100 reviews

A newly renovated home showcases a green exterior with a metal roof. A welcoming front porch spans the width of the house, featuring multiple entry points and shaded by surrounding trees. A gravel driveway leads up to the home, offering ample outdoor space and a peaceful setting.

Home in Ripton

cozy home for a relaxing fall getaway

5 out of 5 average rating, 158 reviews

The exterior of a renovated one-room schoolhouse is presented, set amidst lush green foliage. A vibrant red door stands out against the white walls, while a well-maintained hedge borders the property. Surrounding trees provide a serene backdrop, creating a peaceful atmosphere.

Home in Rutland

One Room School House. No Cleaning Fees!

4.98 out of 5 average rating, 128 reviews

A spacious living area features exposed wooden beams and a cozy arrangement of leather seating. A modern flat-screen television is mounted on the wall, across from a wooden dining table. Nearby, a stone fireplace adds a rustic touch, complementing the open kitchen layout.

Home in Windsor

Stylish Vermont Cabin | Views · Trails · Luxe

4.96 out of 5 average rating, 337 reviews

Home in Clarendon

Killington Retreat | Deck-Fire Pit-Mountain Views!

4.98 out of 5 average rating, 178 reviews

A well-appointed bedroom showcases a spacious bed dressed in white linens, complemented by decorative pillows. A wooden bench is situated at the foot of the bed. A large mirror and artful wall decor enhance the serene atmosphere, while natural light enters through a large window.

Home in West Windsor

Birdie's Nest Guesthouse

4.97 out of 5 average rating, 230 reviews

A warmly lit cabin emerges from the surrounding trees, framed by a quiet, snow-covered dirt road. Soft light spills from the windows, creating a welcoming glow in the tranquil, darkened landscape.

Home in Rochester

The Guest House at Sky Hollow

Apartment rentals with outdoor seating

5 out of 5 average rating, 119 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, 361 reviews

Flat in Clarendon

Dog heavenly! Private, beautiful and relaxing.

4.96 out of 5 average rating, 123 reviews

A stone patio is illuminated by string lights, featuring a fire pit surrounded by three adirondack chairs in red, blue, and white. Lush greenery is visible in the background, creating a serene outdoor gathering space.

Flat in Ludlow

Peaceful Ludlow base for exploring Okemo valley

4.95 out of 5 average rating, 112 reviews

A serene lake scene is presented at sunset, with a solitary kayaker navigating the calm waters. The reflection of the sun creates a shimmering path across the lake's surface, while trees line the distant shore, adding to the peaceful atmosphere.

Flat in Leicester

Hideaway Lodge at Lake Dunmore Cozy VT Retreat

5 out of 5 average rating, 265 reviews

A flowing waterfall cascades over rocky terrain, surrounded by lush greenery. Sunlight filters through the trees, creating a serene atmosphere. The water splashes against large stones, while vibrant foliage frames the scene.

Flat in New Haven

Dog Team Falls Apartment - Minutes from Middlebury

5 out of 5 average rating, 282 reviews

A cozy bedroom features a spacious bed with a white quilt and decorative pillows. Natural light enters through two windows, illuminating the room's soft blue walls. A bedside table with a lamp is positioned next to the bed, adding functional charm to the space.

Flat in Chittenden

Vermont Country Suite

4.99 out of 5 average rating, 128 reviews

The exterior of the white house is framed by green landscaping, featuring black shutters on the windows. A covered porch with hanging flower baskets invites visitors, while solar panels sit atop the roof. A well-maintained garden complements the welcoming atmosphere.

Flat in Hancock

Two-Bedroom apartment in the Green Mountains

4.91 out of 5 average rating, 127 reviews

The rustic farmhouse is set on a spacious green lawn, showcasing a classic red exterior with a metal roof. Large windows provide ample natural light, and the surrounding trees create a serene country atmosphere.

Flat in West Rutland

Mountain View Apartment

Apartment rentals with outdoor seating

4.99 out of 5 average rating, 144 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

4.95 out of 5 average rating, 126 reviews

A bright living area is furnished with a sectional sofa in teal and a wooden coffee table. A fireplace with a brick surround adds warmth. Light streams through glass doors leading to a balcony, while wall art provides color and personality to the space.

Apartment in Warren

Ski-in, Ski-Out / 4 beds / seasonal pool

4.89 out of 5 average rating, 124 reviews

The exterior of the building is shown against a backdrop of a green and orange hillside. Surrounding landscaping includes neatly trimmed bushes, with a paved parking area featuring two parked cars. The structure has a mix of stone and brick accents, complemented by gray roofs.

Apartment in Mendon

105 Fox Hollow Village Pvt - Red Fox - Unit B-4

4.76 out of 5 average rating, 105 reviews

Book Now for Spartan Race, Brewfest, Harvest Faire

The living area features a spacious navy sofa adorned with colorful pillows and a light wooden coffee table. A round dining table with black chairs is present, alongside a large mirror and soft lighting that enhance the inviting space. Natural light filters through the sliding doors.

4.9 out of 5 average rating, 154 reviews

Cozy Mountain Retreat w Views | Pool, Hot Tub, Ski

A modern studio space is presented with wood paneling and a vaulted ceiling. Stainless steel kitchen appliances are featured alongside a dining table and a comfortable seating area. Two vintage ski boards are mounted on the wall, and a sliding glass door provides access to a private balcony.

4.78 out of 5 average rating, 334 reviews

Serene Top Floor Condo (resort style amenities)

A dining area is set with a wooden table adorned with plates and glassware, complemented by a stylish chandelier overhead. In the background, a comfortably furnished living area features a sofa and a smart TV, creating a welcoming environment.

4.89 out of 5 average rating, 176 reviews

Modern Killington Farmhouse Condo: Close to Resort

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.