Vacation rentals with a patio in Pittsfield

Guest suite in Lake Bomoseen

An aerial view showcases a large, red two-story building with a metal roof nestled among lush greenery. The property features multiple decks and a private outdoor space. The surrounding landscape provides a serene backdrop of trees and grass, enhancing the natural setting.

4.97 out of 5 average rating, 249 reviews

My house is your house!

Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K w/ surround sound. w/ game hook-up. Wi-Fi. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage.Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 15 miles to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

4.93 out of 5 average rating, 159 reviews

Home in Killington

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

Our 2-bedroom, 2.5-bath Airbnb, nestled in Vermont’s Green Mountains, invites you to escape into a haven of year-round adventure. Enjoy breathtaking views of a scenic pond, skiing through pristine slopes, bike along winding trails, or hike amidst the number 1 ranked foliage in the USA. Rejuvenate in the indoor pool and spa, with hot tubs, steam rooms, sauna and gym. Unwind by the cozy fireplace, creating unforgettable memories. Pool and Spa area closed May 4 to May 15 for annual Maintenance

5 out of 5 average rating, 159 reviews

Home in Killington

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!

The Big Lebearski is a modern Killington home located just off the main road and close to everything. While you relax at our home after a day on the mountain, you can catch a movie on one of our smart TVs, relax in the outdoor hot tub, roast s'mores at the fire pit, enjoy a drink at the motorcycle bar, shoot hoops in the game room or sit by the wood burning fire. This home is perfect for groups and families to spread out and enjoy all that Killington has to offer. Central AC - rare in Vermont!

4.98 out of 5 average rating, 122 reviews

An exterior view of the home showcases a patio adorned with string lights, providing a warm glow against the backdrop of rolling green hills. The hot tub is visible nearby, adding to the inviting outdoor space perfect for gatherings.

Cabin in Killington

Camp Poe: Hot Tub/Game Room/6acres/Patio/EV Chrgr

Experience the heart of the Green Mountains on our private 6 acre estate. Camp Poe at Estabrook is the ultimate Vermont getaway--wide plank floors, fully stocked farmhouse kitchen, wooden beams and a two story family room w/ a wood burning stove. This 3200 sq ft house is perfect for entertaining with two separate living rooms, bar, game room, 10ft dining tables (inside AND outside) and hot tub. 13 min to Killington Mtn & 4min to the #1 golf course in VT! EV Charger available for guest use.

4.98 out of 5 average rating, 289 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.

4.99 out of 5 average rating, 112 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!

Welcome to our cozy 2BR/1BA cabin, ideal for 6 guests. Relax by the indoor fireplace or outside by the fire pit and hot tub. Listen to the stream from the patio. Fully equipped kitchen and washer/dryer for convenience. Only 10 mins from Dartmouth College and 5 mins to downtown Norwich, VT. Multiple ski resorts within 30-minutes. Perfect for a serene getaway, this cabin offers a blend of comfort, nature, and convenience, ensuring a memorable stay for family, friends, or a romantic retreat!

4.98 out of 5 average rating, 127 reviews

Home in Windsor

Stylish Vermont Cabin | Views · Trails · Luxe

There is something about spring and summer at the Red House that makes you stop and gaze. Watch the hills come back to life from the porch, coffee in hand, as green rolls up the valley and wildflowers take over the fields. Hike or bike to a trailhead five minutes from the front door. Gather around the fire pit and wonder how dark and wide the night sky can be. The Red House sits within reach of some of the best restaurants in New England and patiently awaits the discerning traveler.

4.98 out of 5 average rating, 174 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

Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

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.

4.99 out of 5 average rating, 303 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*

4.97 out of 5 average rating, 158 reviews

A stone pathway is framed by lush greenery and garden beds leading to the entrance of the chalet. Soft lighting from lanterns illuminates the steps, creating a welcoming atmosphere as it transitions from the natural surroundings to the home's entrance.

Chalet in Stockbridge

Gnome Home Mountain Ski Chalet w/Sauna Killington

Mountaintop Chalet perched in the heart of Green Mountains. Enjoy true mountain living all year long 25m to Killington, White River access minutes from home, abundance of hiking trails, and golf courses. Central to Killington, Rochester, & Woodstock. After your adventures, return to a welcoming & comfortable home with beautiful views from every room, multiple decks, new! fireplace, & sauna, and plenty of special touches to help you unwind and relax.

4.94 out of 5 average rating, 141 reviews

A private deck with a hot tub is surrounded by colorful planters filled with seasonal flowers and pumpkins. The entrance to the cabin features a welcoming door framed by autumn decorations, backed by lush greenery from the surrounding forest.

Cabin in Chittenden

Outside Inn - Hot Tub/Killington/MtnTop Inn/VAST

Reconnect with nature at the Outside Inn, a four season retreat, locally known as the Labor of Love. A man fell in love with a woman, but when he asked for her fathers blessing he said, first you must build her a home. So he built this beautiful post and beam cabin and they lived happily ever after! *Decorated seasonally!* IG/TikTok: outside_inn_vt FB: Outside Inn VT

Popular amenities for Pittsfield patio rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

4.92 out of 5 average rating, 51 reviews

An open-concept living area features a light-colored sofa arranged with a soft throw. A small dining bar with green cabinetry is visible, balanced by pendant lighting above. Kitchen utensils hang on the wall, and natural light enters through the windows, enhancing the welcoming ambiance.

Apartment in Vergennes

Little City Brick Apt A - Downtown Vergennes

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.

Apartment in Mount Tabor

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

4.93 out of 5 average rating, 71 reviews

A bright living area features large windows that allow natural light to fill the space. A light-colored sofa and armchair are accompanied by a round coffee table and a woven rug. A bookshelf displays decorative items, and a TV is positioned for viewing.

Apartment in Rochester

Green Mountain Collection: Cozy Vermont Haven

4.97 out of 5 average rating, 131 reviews

A spacious living room is depicted featuring comfortable sofas and a stylish coffee table. Natural light enters through a window with dark curtains, while a decorative rug adds warmth to the wood floor. A welcoming entryway is visible in the background.

Apartment in Middlebury

Middlebury Grand Family Retreat | Fast Fiber WiFi

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

4.97 out of 5 average rating, 150 reviews

A spacious bedroom features a large bed adorned with a textured gray blanket and multiple pillows. Elegant curtains frame the two windows, allowing natural light to filter in. Decorative lamps provide a warm glow, while art pieces add character to the walls.

Apartment in Randolph

Beautiful private village apartment with king bed

4.99 out of 5 average rating, 177 reviews

A spacious living area features a queen size bed with a blue quilt, adjacent to a cozy fireplace. Green armchairs and a small round table provide additional seating. Tall curtains frame windows, and a bookshelf adds a touch of color to the wall.

Apartment in Middlebury

Bluebird Studio- Light filled and airy

4.95 out of 5 average rating, 39 reviews

A cozy bedroom is presented, featuring a spacious bed adorned with a soft yellow and white bedspread. Two lamps on nightstands cast a warm glow. A framed landscape photo hangs above the bed. The room is softly lit, creating a relaxed atmosphere.

Apartment in Bethel

Brookside

House rentals with a patio

5 out of 5 average rating, 26 reviews

A log-style home is set amidst a spacious green lawn and trees. The stone chimney and patio chairs are visible under a covered porch, with the path leading to the entrance. Soft sunlight filters through the leaves, creating a serene ambiance.

Home in Woodstock

Fabulous Log Home in the Woods

4.89 out of 5 average rating, 226 reviews

A new hot tub with jets is positioned under a wooden structure, surrounded by grass and landscaped areas. A tranquil view of distant mountains and trees is visible in the background, creating a peaceful outdoor setting.

Home in Rutland

Killington/Okemo, 7p Hot tub, Mtn.views, Spacious!

5 out of 5 average rating, 23 reviews

Home in Warren

Sky Zen - Ridgeline Retreat

4.79 out of 5 average rating, 95 reviews

A cozy house is set against a snowy landscape, featuring a covered front porch with white railings. The exterior showcases neutral tones and is surrounded by trees, providing a secluded atmosphere. Snow covers the ground, enhancing the peaceful winter scene.

Home in Stockbridge

Ski, snow mobile, hiking, fun on slopes & trails!

4.93 out of 5 average rating, 58 reviews

A charming farmhouse is showcased, featuring a sloped metal roof and a welcoming porch adorned with hanging planters. Green grass surrounds the property, framed by large trees, while open fields can be seen in the background under a clear blue sky.

Home in Bethel

Fred Eddy Farmhouse

5 out of 5 average rating, 14 reviews

A warm hot tub is presented against a snowy landscape, surrounded by trees bare of leaves. The distant view of the reservoir is framed by the serene white of winter, inviting relaxation and tranquility.

Home in Chittenden

Modern Retreat, Mountain Top Inn, Killington, Pico

4.98 out of 5 average rating, 44 reviews

A spacious living area showcases wooden beams and warm-toned walls. Large windows allow natural light to enter. Furnishings include two sofas, a coffee table, and various side tables. A vibrant area rug covers the wooden floor, and decorative plants add a touch of greenery.

Home in Waitsfield

Charming and Centrally Located Waitsfield Home.

5 out of 5 average rating, 52 reviews

A two-story gray house with an A-frame design is surrounded by trees. Large windows fill the front facade, allowing natural light inside. A spacious wooden deck features multiple seating areas and an umbrella, promoting outdoor relaxation.

Home in Mendon

The Old Home Place!

Condo rentals with a patio

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.

Condo in Ludlow

Main St Escape | Explore Downtown Ludlow

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

A modern living room features a cozy fireplace, with decorative skis mounted above it. A large TV is positioned on a stylish media console, while a comfortable sofa and ottoman provide ample seating. Large windows allow natural light to brighten the space.

4.98 out of 5 average rating, 52 reviews

Killington Condo-Indoor Pool/HotTub/FitnessCenter

4.96 out of 5 average rating, 89 reviews

FUN 2BR/2BA Condo – Pool, Spa & Walk to Lift!

A tranquil sleeping area features a cozy bed with soft bedding and accent pillows. Nightstands with lamps are placed on either side, providing gentle light. A large horse portrait adorns the wall above the bed, contributing to the serene ambiance.

4.91 out of 5 average rating, 105 reviews

Great Deal Cozy 2 Bedroom .2 mi to lift

4.94 out of 5 average rating, 104 reviews

A living area features a gray sofa adorned with decorative pillows in various patterns. A wooden coffee table sits in front, and a side table with a lamp complements the space. Light filters through a sliding glass door, which opens to a patio.

Condo in Ludlow

Ground Floor, Okemo True Ski-in/Ski-Out

4.94 out of 5 average rating, 49 reviews

A snow-covered landscape is captured, featuring frosted trees along a winding path. The sun is positioned low in the sky, casting a soft glow over the snowy terrain. Rolling hills and distant mountains create a serene backdrop, all under a cloudy sky.

Condo in Mendon

Mountain Hideaway two bedroom condo Near PICO MTN