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Holiday rentals with a patio in Windsor County

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Top-rated rentals with patio in Windsor County

Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.

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Top guest favourite
An open-concept kitchen and living area are highlighted by high ceilings and large windows, allowing natural light to fill the space. A central island with a dark countertop complements the cabinetry, while a cozy seating area is visible through expansive glass doors opening to the outdoors.
Home in Windsor
4.98 out of 5 average rating, 129 reviews

Stylish Vermont Cabin | Views · Trails · Luxe

Combining sweeping views of distant hills with complete privacy and wraparound porches on two sides, the Red House is a custom cabin built for couples and smaller families. Surrounded by working farms and within easy reach of trailheads to hike or bike Mt Ascutney, or to visit Woodstock, Hanover, Ludlow and the Upper Valley, the Red House sits among some of the best restaurants in Vermont and awaits the discerning traveler who has earned the right to do absolutely nothing and experience it all.

Top guest favourite
Home in Bridgewater
5 out of 5 average rating, 100 reviews

Breathtaking Riverfront Retreat w/Mountain Views

Thoughtfully designed to elevate every moment of your Vermont getaway, our home offers a comfortable & uniquely historic experience, along with panoramic views of the beautiful Ottauquechee River. Perfectly nestled between the vibrant towns of Woodstock and Killington, guests have incredible hiking, skiing, golfing, shopping, leaf peeping, delicious dining, and so much more right at your finger tips. Wonderful for families, couples, or small groups looking to explore all that VT has to offer!

Guest favourite
The cabin entrance is framed by freshly fallen snow, with wooden siding that blends into the winter landscape. A lantern on the left provides a soft glow, illuminating the path. Tranquil trees surround the area, enhancing the serene atmosphere.
Cabin in Plymouth
4.99 out of 5 average rating, 129 reviews

~The ClubHaus~

Appreciate life at our peaceful home away from home in the Vermont Woods... Located a short drive from Killington and Okemo ski mountains, The ClubHaus is the perfect spot to unwind after enjoying four season New England activities. Breweries and great food are nearby in Woodstock, Manchester, and Dorset. Huge fireplace, hot tub, comfortable beds, and lots of thoughtful touches provided to welcome you to the ClubHaus family. Wifi, Netflix, and Disney+ included, no cable. @clubhausvt on IG

Top guest favourite
A master bedroom features a vaulted ceiling and coral-colored walls. A spacious bed is centered beneath large windows, allowing natural light to fill the room. A cozy bench with decorative accents rests at the foot of the bed, and bedside lamps provide ambient lighting.
Guest suite in Norwich
5 out of 5 average rating, 156 reviews

In-Town Norwich 1.5 miles to Hanover/Dartmouth

Located in the center of Norwich, this modern townhome-style accommodation is a wing attached to our residence. Enjoy your upstairs master suite + office/2nd bedroom, downstairs "café" and all-season sunroom. Relax with a view to the garden and woods beyond. We are 1.5 miles to Hanover/Dartmouth, and 1.0 mile to King Arthur Baking. Our street is part of the Appalachian Trail, and you will be near many Upper Valley attractions. We live onsite and are available to assist you upon request.

Top guest favourite
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
4.99 out of 5 average rating, 122 reviews

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!

Guest favourite
The exterior of Bearfoot Cottage is highlighted, featuring a combination of wood and metal finishes. A spacious deck with steps leads to the entrance, framed by large windows. A fire pit sits nearby, complemented by comfortable seating arrangements on the gravel surface.
Tiny home in Chester
4.97 out of 5 average rating, 175 reviews

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Tiny living at its best! Welcome to Bearfoot Cottage, a custom-designed Tiny House escape nestled on 15 acres in Southern Vermont. Enjoy the entire property to yourself with hot tub, Char-Griller BBQ, & Solostove firepit. Hike or snowshoe Ladybug Trail to our babbling brook. Then explore the best of Okemo Valley all at your fingertips! Ski/Snowboarding (+more Winter sports), biking, hiking, fishing, dining, breweries, and live music/nightlife. Your vacation is what you make it!

Top guest favourite
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
4.98 out of 5 average rating, 181 reviews

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.

Top guest favourite
A modern fire pit is illuminated in the evening, surrounded by a wooden enclosure. The design features an open, triangular mesh body that reveals flickering flames within. Soft light casts a warm glow on nearby seating, providing a cozy atmosphere for gathering.
Home in Ludlow
4.97 out of 5 average rating, 105 reviews

Mountain views - hot tub, games, minutes to lakes

Enjoy our 3900 square ft home with 5 bedrooms and 3 full bathrooms, large kitchen and dual dining areas. Enjoy the Buck Hunter arcade game, a 75-inch TV, a stocked library and shuffleboard table. Relax in the backyard with a fire or a dip in the Jacuzzi hot tub. Sleeps 12. Explore nearby Woodstock, Manchester and Weston. Okemo & Jackson Gore resorts are less than 10 minutes away. Killington Mtn 30 min drive. Enjoy hiking, fishing, biking, kayaking, skiing & golf nearby.

Guest favourite
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, 165 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.

Top guest favourite
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
4.97 out of 5 average rating, 163 reviews

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.

Top guest favourite
The exterior of an 1840s stone house is displayed, featuring a warm red door and large windows under a sloping roof. A well-maintained garden surrounds the entrance, and a tall tree provides shade. A gravel path leads to the house, with a visible stone wall along the yard.
Cottage in Chester
4.91 out of 5 average rating, 120 reviews

Quaint stone house!

⭐️ 2022 Rockingham Old House Award ⭐️ Take it easy at this unique and tranquil getaway. The Cairn of Vermont is an 1840s stone house located in the sleepy remnants of Bartonsville Village, now part of Chester, VT. 20 minutes to skiing and hiking, biking and the great outdoors are all around you! Less than 5 minutes to Vermont Country Store and make your way home through the Bartonsville Covered Bridge!

Guest favourite
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
4.94 out of 5 average rating, 143 reviews

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 rentals with patio in Windsor County

KitchenWifiPoolFree parking on premisesAir conditioning

Flat rentals with a patio

Guest favourite
A rustic barn conversion features a white exterior with multiple windows that reflect natural light. An ADA compliant ramp provides accessible entry, leading to a wooden deck surrounded by grassy area and trees. The clear blue sky creates a serene backdrop.
Flat in Randolph
4.81 out of 5 average rating, 78 reviews

Cozy VT 1st floor apartment

Guest favourite
A wooden deck is shown with a round table surrounded by four metal chairs. A large red umbrella provides shade over the table, while lush greenery is visible in the background, creating a sense of privacy and tranquility.
Flat in Lebanon
4.83 out of 5 average rating, 77 reviews

Lovely Duplex with Deck and Central Location

Top guest favourite
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.
Flat in Rochester
4.93 out of 5 average rating, 73 reviews

Green Mountain Collection: Cozy Vermont Haven

Top guest favourite
Flat in Ludlow
5 out of 5 average rating, 11 reviews

Cozy Mountain-style Condo by Okemo with a View!

Guest favourite
The exterior of the condominium is framed by a well-maintained fence and lush shrubbery. Colorful foliage adds vibrancy to the entrance, which features a welcoming pathway leading to a front door partially obscured by a small overhang.
Flat in Hanover
4.95 out of 5 average rating, 43 reviews

2 BR Condo, 5 minute walk from Dartmouth campus

Top guest favourite
A cozy studio apartment showcases a wood-burning stove located on a brick hearth. A dark sofa is positioned across from a flat-screen TV mounted on the wall. The space is illuminated by sunlight through two windows, draped with sheer white curtains.
Flat in Thetford
4.99 out of 5 average rating, 74 reviews

Cozy Studio Apartment

Top guest favourite
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.
Flat in Randolph
4.97 out of 5 average rating, 159 reviews

Beautiful private village apartment with king bed

Top guest favourite
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.
Flat in Bethel
4.95 out of 5 average rating, 40 reviews

Brookside

House rentals with a patio

Guest favourite
A serene view showcases a house nestled in a wooded area, surrounded by tall trees and patches of snow. The property features a clear driveway leading to the main home, accentuated by a charming red-roofed structure nearby. The landscape blends nature and tranquility.
Home in Plymouth
4.95 out of 5 average rating, 66 reviews

Killington - Woodstock: Private Oasis w/ Hot-Tub

Guest favourite
A charming cottage with a pitched roof is surrounded by lush greenery. The gravel driveway leads up to the entrance, where a porch can be seen. Large trees provide shade and enhance the natural setting of the exterior.
Home in Bridgewater
4.91 out of 5 average rating, 53 reviews

Quaint Cottage

Top guest favourite
The bright kitchen showcases a spacious island with seating for four at sleek, modern bar stools. Stylish pendant lights hang above, and large windows provide natural light. Ample cabinetry lines the walls, with contemporary appliances positioned for easy access.
Home in Hartford
4.94 out of 5 average rating, 124 reviews

Quechee Getaway See the Vermont MTNs

Top guest favourite
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
5 out of 5 average rating, 27 reviews

Fabulous Log Home in the Woods

Top guest favourite
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
4.89 out of 5 average rating, 235 reviews

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

Guest favourite
A serene exterior view of the timber-frame home is presented amidst a lush green lawn, surrounded by vibrant autumn foliage. The private pond and distant hills enhance the tranquil setting, while a large tree provides shade beside the inviting outdoor space.
Home in Mount Holly
4.91 out of 5 average rating, 34 reviews

Stunning 3 br Timber Frame ski retreat on 6 Acres

Guest favourite
Home in Barnard
4.97 out of 5 average rating, 29 reviews

The Looking Glass, a modernistic escape

Guest favourite
A modern cabin stands surrounded by lush greenery, featuring a dark exterior that contrasts with the natural landscape. A spacious deck is supported by wooden beams, and large windows invite natural light. A stone wall borders the property, adding character to the setting.
Home in Killington
5 out of 5 average rating, 24 reviews

Skye Ridge Lodge: Private Hot Tub, Open Concept

Apartment rentals with a patio

Top guest favourite
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
4.99 out of 5 average rating, 144 reviews

Main St Escape | Explore Downtown Ludlow

Guest favourite
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.
Apartment in Killington
4.95 out of 5 average rating, 169 reviews

AC | Dog-Friendly | Bike, Hike & Relax

Guest favourite
A cozy living area features a spacious sectional sofa and a wooden coffee table, with candles placed on top. Artwork depicting mountain scenes decorates the wall, while a glass door leads to the private balcony, allowing natural light to brighten the space.
Apartment in Mendon
4.93 out of 5 average rating, 91 reviews

¤5-15 Mins to Ski Slopes | Fast WiFi | Fireplace¤

Guest favourite
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.
Apartment in Killington
4.92 out of 5 average rating, 108 reviews

Bike park open Cozy 2 Bedroom .2 mi to mountain

Guest favourite
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.
Apartment in Ludlow
4.94 out of 5 average rating, 105 reviews

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

Top guest favourite
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.
Apartment in Mendon
4.94 out of 5 average rating, 50 reviews

Mountain Hideaway two bedroom condo Near PICO MTN

Guest favourite
A modern kitchen area features a gray dining table surrounded by four black metal chairs. A wall clock hangs above the table, while white cabinetry and appliances are visible in the background. Natural light brightens the space, creating a clean and inviting atmosphere.
Apartment in Hartford
4.93 out of 5 average rating, 58 reviews

Christian Street Condo w/ Screened In Balcony

Top guest favourite
The living area features a modern design with a mounted television above a sleek electric fireplace. Plush seating includes a cozy couch and two armchairs, accompanied by a stylish coffee table. Light-colored curtains frame the windows, enhancing the room's bright ambiance.
Apartment in Rutland
4.93 out of 5 average rating, 69 reviews

Luxury, downtown apt w/ balcony close to skiing

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