Vacation rentals with outdoor seating in West Windsor

4.97 out of 5 average rating, 201 reviews

A charming cottage is set against a backdrop of lush trees, with a deck extending from the front. The warm, orange sky creates a serene atmosphere, casting soft light on the exterior of the house and surrounding landscape.

Guesthouse in Hartland

Cozy - Killington 40 min. Woodstock-Hanover-Piano!

Luxurious, well appointed cottage - Beautiful sunrise view located between Woodstock VT and Hanover NH. Inspiring treat for musician’s getaway is a fully restored 1929 Steinway Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer. VERY comfortable queen bed. Romantic getaway in the woods, relax, work in peace, explore the beauty and history of the area. Hiking, biking, fishing, hot air balloon rides and shopping are all close by. Long (90 day) or weekend rental

Superhost

A rustic cabin surrounded by tall trees is showcased. A light-colored entrance door and two windows are displayed at the front. Adjoining the cabin, a grassy area features a stone pathway leading to a pair of white adirondack chairs, inviting relaxation.

Guest suite in Hartford

4.88 out of 5 average rating, 154 reviews

Adorable one bedroom studio in 1844 farmhouse.

Keep it simple at this peaceful and centrally-located place. We have a beautiful 1844 farm house located in Quechee, that has been in our family for over a hundred years. It is located less than a 1/4 mile from the Quechee Gorge and Antique Mall. The farm includes fifty acres of land and trails with wonderful views of Mt. Ascutney, Killington and more. We also abut the state park which has twelve hundred acres of land. All perfect for hiking, snowshoeing, snowshoeing, biking or just relaxing.

4.96 out of 5 average rating, 274 reviews

The rustic cabin, surrounded by lush trees, features a porch with a picnic table. The wooden structure is designed with a gabled roof and large windows, providing a welcoming entrance. Flower boxes adorn the front, enhancing the natural setting.

Cabin in West Windsor

Sunset Cabin - your private romantic hideaway

Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; this rustic, pet friendly cabin is a perfect romantic hideaway. Two trout ponds are steps from your door for fishing and swimming. Just minutes from Mt. Ascutney's hiking/biking trails and in the middle of fantastic cycling country. Near local race including the VT100, Vt overland, VT50. Sunset Cabin is a marvelous spot for enjoying fall foliage and exploring VT!

4.99 out of 5 average rating, 735 reviews

A cozy living area features a mixture of seating options, including a tufted sofa and a vintage-style sofa adorned with decorative cushions. Natural wood floors enhance the warmth of the space, while artwork on the walls and a circular coffee table complete the inviting atmosphere.

Barn in Chester

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

4.98 out of 5 average rating, 173 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.

Apartment in Weathersfield

The exterior of a modern blue house is depicted, featuring a combination of angular roofs and large windows allowing for ample natural light. A stone wall borders the property, which is surrounded by lush greenery and trees in the background.

4.99 out of 5 average rating, 188 reviews

The Loft at Weathersfield

Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.

4.81 out of 5 average rating, 196 reviews

The historic farmhouse features a white exterior with a gabled roof, surrounded by lush greenery. A large tree provides shade in the front yard, and flower gardens can be seen along the stone pathway leading to the porch, which has seating for relaxation.

Apartment in Taftsville

Quiet Vermont Farmhouse

Rent a quiet two-bedroom apartment in our 1850's farmhouse in historic Taftsville, Vermont. We are close to the fascinating history, arts, and shopping of Woodstock VT, and near several downhill and cross country ski and snowshoe centers, Marsh-Billings-Rockefeller National Historical Park, and lots of hiking trails, as well as within a short drive of Hanover NH and White River Junction VT. Come enjoy our warm hospitality, wander our gardens, and enjoy our shared patio.

4.98 out of 5 average rating, 290 reviews

A cozy cabin is nestled among the trees, showcasing a rustic wooden exterior with large windows. It overlooks a gentle slope covered in green grass and wild plants, with sunlight filtering through the canopy above, creating a serene and inviting atmosphere.

Guesthouse in Woodstock

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.

4.95 out of 5 average rating, 101 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, 121 reviews

The exterior of a two-story home is set among vibrant gardens filled with colorful flowers. A neatly maintained lawn extends toward a shaded area featuring rustic seating. Lush trees and greenery complete the serene landscape, providing a peaceful and inviting outdoor atmosphere.

Home in West Windsor

Mt Ascutney Retreat Near Okemo | 3BR w/ Fireplace

Peaceful 3BR Vermont Estate Near Woodstock & Mt. Ascutney Escape to our serene Vermont retreat on 7 private acres. Just 5 minutes from Mt. Ascutney trails and 15 minutes from Green Mountain Horse Association. Perfect for families, riders, and nature lovers, our modern country home blends comfort with classic Vermont charm. Whether you’re planning a quiet couples’ retreat or a family getaway full of Vermont adventure, you’ll find space, serenity, and style here.

4.95 out of 5 average rating, 1,036 reviews

The spacious interior of the yurt features a circular design with natural wood and fabric elements. Comfortable seating areas include a queen-sized futon and a wooden sofa. Large windows allow natural light to fill the space, while a wood stove provides warmth.

Guesthouse in Hartland

Yurt In The Woods - Come to the Yurt.

The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for Weekends. October 6th and 12th are currently vacant if you want a fall foliage trip. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available May - October

4.98 out of 5 average rating, 497 reviews

The Kingsley Grist Mill is positioned alongside a flowing river, surrounded by trees showcasing autumn colors. A historic covered bridge is visible in the distance, enhancing the landscape. The building features multiple stories with varying textures and roof styles, reflecting its rich history.

Castle in Rutland

Kingsley Grist Mill Waterfall & Private Beach OMG

One of the "World's Most Amazing Vacation Rentals " as seen on the exciting NetFlix series, s.2, ep.7 and on HGTV's "You Live in What?, s.2, ep.1. Join us this season for the romance, the history, the breakfast, the natural mineral spring tap water, the concert, the rafting, the architecture and the legacy of the KGM, Vermont's Wright-esque falling water masterpiece. No cleaning fees added. Come make history with us ! Near Killington & Okemo Mtns.

Popular amenities for West Windsor outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.96 out of 5 average rating, 157 reviews

A charming home is set among lush greenery, featuring a screened porch and a vibrant orange front door. Flowering shrubs and stones create a welcoming landscape, while tall trees provide privacy and shade.

Home in Cornish

Country Home next to Covered Bridge

4.87 out of 5 average rating, 122 reviews

A sign reading 'The Oaks' is prominently displayed in front of the property. Colorful metal flowers are set in the lush green grass, framed by a backdrop of blooming trees and a partially visible building. Soft clouds pass overhead, creating a serene outdoor atmosphere.

Home in Plainfield

The Oaks - secluded rural estate w/ amazing views

4.95 out of 5 average rating, 111 reviews

A bright yellow wall features a modern artwork piece framed above a set of wooden steps. The wood accent of the steps complements the white wainscoting that runs along the base of the wall.

Home in Bethel

Comfortable 3 Bedroom King size Master w/ En suite

5 out of 5 average rating, 108 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, 161 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

4.95 out of 5 average rating, 169 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, 174 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

4.96 out of 5 average rating, 122 reviews

A serene lakeside setting is presented, featuring a stone patio bordered by natural boulders. Colorful adirondack chairs in blue and green invite relaxation. A wooden dock extends into the calm water, with trees and hills visible in the distance under a cloudy sky.

Home in Enfield

Quiet lakeside retreat with private dock.

Apartment rentals with outdoor seating

4.93 out of 5 average rating, 264 reviews

An outdoor deck features a round table surrounded by four black metal chairs, offering a panoramic view of rolling hills and trees. The clear blue sky complements the lush greenery of the landscape.

Apartment in Townshend

Private Apt. on Farm, Hot Tub with views!

4.93 out of 5 average rating, 162 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.

Apartment in Chester

Lovely 2 Bedroom Apartment w/deck & pond view

4.95 out of 5 average rating, 157 reviews

Apartment in Springfield

Connecticut River Odyssey

4.95 out of 5 average rating, 354 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.

Apartment in Rutland

Dog heavenly! Private, beautiful and relaxing.

5 out of 5 average rating, 108 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.

Apartment in Rutland

49 River Street

4.96 out of 5 average rating, 117 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.

Apartment in Ludlow

Peaceful Ludlow Base 5 minutes to Okemo

4.99 out of 5 average rating, 147 reviews

A spacious apartment is reflected in the calm water of a pond, surrounded by lush greenery. The building's exterior features large windows and a welcoming design, while the natural landscape adds to the serene setting.

Apartment in Thetford

Charming & Peaceful Upper Valley 1BR Retreat

4.93 out of 5 average rating, 118 reviews

A cozy bedroom is featured, furnished with a spacious bed adorned with decorative pillows. A vintage dresser and a chair add charm to the room, while an elegant lamp and a mirror enhance the ambiance. Floral wallpaper complements the warm carpet design.

Apartment in Ludlow

Charming Suite

Condo rentals with outdoor seating

4.99 out of 5 average rating, 140 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

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, 260 reviews

Cozy Studio for 4 - Walk to Mountain w/Balcony

4.96 out of 5 average rating, 140 reviews

A living area is presented with a spacious purple sectional sofa and an accent chair, creating a comfortable seating arrangement. A wooden coffee table occupies the central space, and large windows allow natural light to fill the room, revealing a snow-covered landscape outside.

Condo in Eastman

Cozy Light-filled Condo in Charming Eastman

Superhost

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.

4.89 out of 5 average rating, 148 reviews

Location + Spa! - Cozy 2BR Condo - Mountain Side

The living area features a cozy seating arrangement with a brown couch and recliners, complemented by a decorative area rug. A coffee table sits in front of the seating, and a dining table with wooden chairs is positioned nearby. Soft lighting enhances the welcoming ambiance.

4.94 out of 5 average rating, 285 reviews

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!

A living room with a gas fireplace built into a brick facade provides warmth. A comfortable sectional couch faces the fireplace, complemented by a small coffee table. Large sliding glass doors open to a balcony, offering views of greenery outside.

4.98 out of 5 average rating, 157 reviews

Cozy Mountain Condo

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, 324 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.