Vacation 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!

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.

A cozy living area features a deep leather sofa positioned near a stone fireplace. A large window opens to the balcony, inviting natural light. A TV is mounted above a wooden mantle, and a small table and chair provide a space for work or dining.

4.99 out of 5 average rating, 160 reviews

Elegant Alpine Condo - Golf, Bike & Pool!

Newly renovated 1-bedroom Whiffletree condo with an upscale alpine feel—just minutes from Killington Resort, golf course and access road. Fully stocked with essentials and includes a locker for your gear. Relax and enjoy the onsite outdoor pool (Open Memorial Day - Labor Day). Easy access to summer fun and scenic Vermont trails! Sleeps up to 4 with a king bed and queen pullout sofa. Baby Pack & Play crib, mattress and sheets available upon request for $25 per stay. Killington Reg #007718

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.

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!

4.94 out of 5 average rating, 385 reviews

A serene lakeside scene captures a cozy cabin nestled among lush trees, illuminated by warm light. A dock extends into the water, featuring seating for relaxation. A canoe glides gently across the lake, adding to the tranquil atmosphere of this picturesque setting.

Cabin in Poultney

Waterfront Vermont Lake House w/ Panoramic Sauna

We invite you to come stay and experience all of the beauty that Vermont has to offer at Lake St. Catherine. Located on the west side of the lake off a quiet private drive with almost 100ft of lake frontage, there are few spots with a better view. Watch the sun rise each morning from either our private decks. Explore the lake by canoe or kayak; both available for our guests. If the dates you're looking for are booked, message us for availability at our second location! Follow us @vtlakehouse

4.98 out of 5 average rating, 292 reviews

A wooden cabin is set against a backdrop of colorful autumn foliage. The exterior features multiple large windows and a spacious deck with seating arrangements, including two lounge chairs. A grill and stacked firewood are visible on the deck, inviting outdoor gatherings.

Cabin in Roxbury

Off Grid Secluded Cabin on 37 Acre Farm

In a secluded, hand-crafted off the grid cabin, come and enjoy the elements with us at Drift Farmstead. A 3-minute walk leads you through gardens and pasture, to Ravenwood, a small, intimate cabin with everything you need. Be it an extended weekend tucked in seclusion, amongst the birds, river and trees, or find the comforts of a 37 acre small farm nestled in the mountains and settle in, working from afar. Top shelf skiing at Sugarbush is near, along with Vermont's finest grub and beer.

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.

4.97 out of 5 average rating, 100 reviews

Chalet in Killington

The Overlook - Views | Hot Tub | Fire Pits | Games

Escape to stunning mountain views at The Overlook. Just 5 min from Killington Resort, restaurants, and shops. Enjoy the peacefulness of this private cozy mountain chalet after a long day of adventure and unwind in the hot tub, game room, or by the fireplace. Convenient Level 2 EV charger compatible with all EVs at the chalet. 🏔️ Mountain View 🌄 Large decks and balcony 🏖️ Hot tub ⚽️ Game room 🍗 Propane grill 🍳 Fully stocked kitchen 🪵 Fire pit 🔥 Fire table ⚡️Level 2 EV Charger

Superhost

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

4.87 out of 5 average rating, 160 reviews

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, 310 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*

4.98 out of 5 average rating, 326 reviews

A spacious living area features large windows framing mountain views and a cozy fireplace. Natural wood accents complement the soft furnishings, including a circular glass coffee table atop a patterned area rug. A dining table for two is positioned near the sliding doors leading to the outdoor deck.

Home in Moretown

Dramatic Views at the Above the Clouds Guesthouse

As featured in Conde Nast Traveler (1/21/22) Peaceful & impeccable retreat with a 180 degree view of Vermont's tallest mountains. Near Vermont's premier skiing, hiking, & outdoor adventures, you’ll love the sunset views and cozy atmosphere (huge sheepskin in front of the fireplace) and the attention to detail (live-edge wood details, spa-like bathroom). This is an incredible retreat for couples and families, adventurers and business travelers alike!

Popular amenities for Pittsfield outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.9 out of 5 average rating, 246 reviews

Aerial view of a snow-covered landscape, showcasing rolling hills and a winding road. The scene includes a mix of bare trees and patches of evergreen, while the distant mountains hint at recreational opportunities. A clear sky and soft sunlight enhance the serene atmosphere.

Home in Killington

Luxury Condo Tucked in the Heart of Killington

4.89 out of 5 average rating, 119 reviews

A comfortable living area features a wood fireplace with tools nearby and a mounted television above it. Two armchairs flank a rustic coffee table, creating a cozy space. Large windows allow natural light to fill the room while offering views of the snowy outdoors.

Home in Killington

Trail Creek - ski home!

4.99 out of 5 average rating, 117 reviews

A red cabin is nestled within a lush green forest, surrounded by trees. A gravel driveway leads up to the entrance, while a vibrant lawn extends in the foreground. The bright blue sky and soft clouds create a serene backdrop.

Home in Norwich

Relaxing Countryside Oasis!

4.99 out of 5 average rating, 160 reviews

A newly renovated house is nestled among tall trees, surrounded by lush greenery. The structure features multiple windows reflecting sunlight, with a wooden deck visible in the foreground, leading to a serene setting that invites outdoor relaxation.

Home in Woodstock

Beautiful Woodstock Home-Perfect for entertaining

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!

4.95 out of 5 average rating, 332 reviews

Home in Clarendon

Killington Retreat | Deck-Fire Pit-Mountain Views!

4.98 out of 5 average rating, 127 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

4.95 out of 5 average rating, 175 reviews

A spacious living area features a modern wood-burning fireplace framed by light brick, with a mounted flat-screen TV above. Comfortable grey sofas and a wooden coffee table are arranged to encourage relaxation, while a wooden staircase leads to the upper level.

Home in Hartford

The Quechee Haus: VT Retreat with Outdoor Hot Tub

Apartment rentals with outdoor seating

4.95 out of 5 average rating, 359 reviews

Apartment in Clarendon

Dog heavenly! Private, beautiful and relaxing.

4.86 out of 5 average rating, 179 reviews

A vibrant autumn landscape is captured, featuring a variety of trees adorned with bright orange, red, and yellow leaves. A winding river is visible in the foreground, surrounded by the lush greenery of the season. Overcast skies provide a soft light over the scene.

Apartment in Bristol

Overlook at the Office

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.

Apartment in New Haven

Dog Team Falls Apartment - Minutes from Middlebury

4.98 out of 5 average rating, 155 reviews

A bright bedroom features a spacious bed adorned with white linens and subtle blue detailing. Natural light enters through two windows, accompanied by blinds. A potted plant adds a touch of greenery, while built-in shelving provides storage options.

Apartment in Middlebury

Mountain View Retreat

4.92 out of 5 average rating, 366 reviews

A spacious outdoor area features vibrant red Adirondack chairs positioned around a circular fire pit. Lush green grass surrounds the seating, while trees and shrubs add natural beauty. A charming two-story building can be seen in the background, inviting guests to enjoy the tranquil setting.

Apartment in Waitsfield

Mountain View Retreat | Private Deck + Fast WiFi

5 out of 5 average rating, 281 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.

Apartment 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.

Apartment in Hancock

Two-Bedroom apartment in the Green Mountains

4.99 out of 5 average rating, 161 reviews

Apartment in Roxbury

Private Resort Luxury in the Heart of Vermont

Condo rentals with outdoor seating

4.99 out of 5 average rating, 143 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.

Condo in Ludlow

Main St Escape | Explore Downtown Ludlow

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.

Condo in Mendon

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

A spacious living area features a plush sofa, a wooden dining table with chairs, and a large window allowing natural light. An electric fireplace is positioned against a stone wall, and a smart TV is mounted above a media console. The decor includes subtle rustic elements.

4.95 out of 5 average rating, 168 reviews

Spring Deals • Quiet Dog-Friendly Mountain Escape

The exterior of a multi-story building is shown, featuring a clock mounted on the facade. Snow covers the ground, and the roof is outlined with snowdrifts. Clear skies are above, contributing to a serene winter atmosphere.

4.76 out of 5 average rating, 105 reviews

Best skiing in yrs; reduced rates

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, 153 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, 333 reviews

Serene Top Floor Condo (resort style amenities)

Superhost

An open living space features a bright red sofa with decorative pillows, complemented by a warm wood dining area with stools. The kitchen, equipped with stainless steel appliances, is visible in the background. Soft lighting creates a welcoming ambiance throughout the suite.

4.89 out of 5 average rating, 253 reviews

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

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.