Holiday rentals with outdoor seating in Chester

4.94 out of 5 average rating, 371 reviews

The rustic cabin features a red exterior with a metal roof, framed by lush greenery. Flower pots with colorful blooms adorn the porch, which includes a small table and chairs. Large windows allow natural light to illuminate the interior.

Cabin in Londonderry

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

4.99 out of 5 average rating, 146 reviews

A spacious living area features a central stone fireplace, surrounded by cozy seating. Large windows frame scenic views of the trees outside, filling the space with natural light. The rustic wooden beams and walls add warmth, while the open layout connects to the kitchen and loft above.

Barn in Andover

Fat Cat Barn - Close Okemo & Magic, Vermont

Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

4.92 out of 5 average rating, 119 reviews

The historic 'Elm House' showcases its bright yellow exterior, framed by lush greenery and a spacious wraparound porch. A nearby structure is visible in the background, featuring a distinctive cupola. The scene is accented by a clear blue sky with scattered clouds.

Home in Chester

Charming 1868 Farmhouse | Okemo & Magic Mtn

Our Historic Victorian is less than a mile to charming Chester Village-enjoy quaint restaurants and pubs, antique shops, art galleries, yoga studio and a country market. Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers, covered bridges + breweries. Close proximity to the best of Vermont's ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington) Come experience why Chester has been voted one of the top 10 most beautiful towns in Vermont!

4.97 out of 5 average rating, 105 reviews

A log cabin is set amidst a snowy landscape, featuring a large wrap-around deck that offers outdoor seating. Snow blankets the ground and the roof, while evergreen trees frame the property, enhancing the secluded ambiance. The stone chimney rises from the cabin, suggesting warmth inside.

Cabin in Cavendish

Pine Ridge Log Cabin Minutes to Okemo & Killington

Get away to Pine Ridge Cabin! A secluded quintessential Vermont log cabin nestled below a pine filled ridge. Have your morning coffee on the large wrap around deck overlooking Elm Brook before your day hiking, brewery hopping, or hitting the slopes! The cabin provides open floor plans centered around the large stone face fireplace, the perfect space for gatherings of family, friends, or a couples retreat! Pine Ridge Cabin is only a few minutes to town, shopping, restaurants, bars, and spa!

4.99 out of 5 average rating, 290 reviews

The cabin's exterior showcases a warm wooden facade with large, strategically placed windows. A spacious screened porch extends from the building, inviting natural light and outdoor enjoyment. A stone pathway leads to the entrance, surrounded by landscaped gravel and native vegetation.

Cabin in Jamaica

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

4.94 out of 5 average rating, 1,326 reviews

The tiny house exterior features a charming porch with colorful railings and vibrant green doors. Tall trees surround the cottage, and a light dusting of snow covers the ground, adding to the serene atmosphere of the setting.

Tiny home in Jamaica

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

4.97 out of 5 average rating, 170 reviews

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

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!

4.99 out of 5 average rating, 733 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, 171 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.

4.99 out of 5 average rating, 187 reviews

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.

Flat in Weathersfield

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.

5 out of 5 average rating, 101 reviews

A historic three-story structure is shown surrounded by snow-covered landscapes, with a backdrop of trees. The red building features multiple windows, showcasing its classic architecture. The Williams River flows alongside, enhancing the serene winter setting.

Home in Chester

Historic Mill • Near Okemo • Fireplaces • Wi-Fi

6-BR, 12+ guests • 18 mins to Okemo, 21 mins to Magic • Hot tub • Fireplaces • Family friendly • Pet friendly • situated along the banks of the Williams River. 1st floor: Two LR's with fireplaces, full bath, large dining room, queen BR; 2nd floor: Large kitchen with fireplace, dining room, full bath, four BR's; 3rd floor: Primary BR suite with sitting area, gas fire, and spa-like bath; separate loft room with twin daybed. Perfect for family gatherings and reunions.

4.93 out of 5 average rating, 160 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.

Flat in Chester

Lovely 2 Bedroom Apartment w/deck & pond view

The perfect Vermont getaway. Lovely new apartment behind retail store on main road to Okemo and Killington for winter skiing and summer adventure. Bedroom, living room, bunk room, fully equipped kitchen, laundry and mudroom. Large deck with pond view, easy access to vacation sites, mountain hiking and biking, discovering Vermont small towns. Experienced, welcoming Airbnb Super Hosts providing all the amenities for a comfortable stay.

Popular amenities for outdoor seating rentals in Chester

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.98 out of 5 average rating, 146 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

4.9 out of 5 average rating, 115 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!

5 out of 5 average rating, 108 reviews

A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.

Home in Bennington

Vermont Farmhouse •Walk to Village & Hiking Trails

4.98 out of 5 average rating, 122 reviews

Home in Windsor

Fresh Snow- Luxury Cabin near Ski Areas

4.93 out of 5 average rating, 141 reviews

A spacious living area features a cozy arrangement of comfortable seating, an inviting coffee table, and a large bookshelf filled with books. Natural light filters through a window, highlighting the greenery outside, while a subtle area rug adds warmth to the wooden floor.

Home in Poultney

Cozy Home in Poultney, Vermont.

4.91 out of 5 average rating, 151 reviews

A cozy bed is adorned with an assortment of pillows in various colors, inviting relaxation. A tray on the bed holds a kettle, two mugs, and a small vase with greenery, while sunlight filters through curtains, illuminating the serene winter landscape outside.

Home in Mount Holly

Newly renovated. Minutes to Slopes & Trails

Superhost

Home in Jamaica

4.86 out of 5 average rating, 310 reviews

Yellow Sweetie at the Base of Stratton

4.98 out of 5 average rating, 415 reviews

A mid-century retreat is illuminated at dusk, surrounded by snow-covered trees. Floor-to-ceiling windows create a warm glow, inviting guests into the living space. The landscape features a serene atmosphere with gently falling snow, enhancing the peaceful setting of the property.

Home in Winhall

Stunning mid-century house on 2.5 private acres

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.

Flat in Townshend

Private Apt. on Farm, Hot Tub with views!

4.95 out of 5 average rating, 258 reviews

A comfortable white sofa with decorative pillows is positioned against a light wall. A small, light-colored side table holds a potted plant. Natural light streams in through a nearby window, illuminating the wooden floor and a blue woven rug beneath.

Flat in Dummerston

HeART Barn Retreat

4.95 out of 5 average rating, 352 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.

Flat in Clarendon

Dog heavenly! Private, beautiful and relaxing.

5 out of 5 average rating, 107 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

4.92 out of 5 average rating, 292 reviews

A one-story cabin is partially enveloped by a blanket of snow, featuring a covered porch with orange railings. The entrance is accessible via a gentle ramp, while trees in the background provide a natural setting. Soft evening light gently illuminates the cabin.

Flat in Ludlow

Okemo Vermont Getaway

4.99 out of 5 average rating, 173 reviews

Two white lounge chairs are positioned around a small black fire pit in a grassy area. Lush greenery and trees define the backdrop, while an open space creates a sense of privacy and tranquility.

Flat in Brattleboro

River View apartment

4.94 out of 5 average rating, 379 reviews

Flat in Poultney

Cozy Poultney Village Apartment

4.95 out of 5 average rating, 125 reviews

A spacious living area features a comfortable, light-colored sofa with multiple cushions. A low, dark wooden coffee table is centered on a textured rug. Green plants are positioned throughout, and ample natural light enters through large windows adorned with simple treatments.

Flat in Putney

Minimal organic hideaway inspired by nature

Apartment 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.

Apartment in Ludlow

Main St Escape | Explore Downtown Ludlow

4.99 out of 5 average rating, 131 reviews

A spacious living area features a large sectional sofa adorned with cozy throw pillows, complemented by a textured area rug. Natural light pours in through expansive windows, enhancing the inviting atmosphere. A side table and a plush armchair add to the comfortable seating options.

Apartment in Dover

Winter Dream! The Handle Lodge at Snowtree Condos

A cozy living area is visible, featuring a dining table surrounded by bright yellow chairs. A fireplace is seen, enhancing the space, while a large bear-themed wall mural adds a touch of nature. Natural light floods in from the nearby window.

4.93 out of 5 average rating, 208 reviews

CozyCub- Location, Ski Off/Shuttle On!

4.95 out of 5 average rating, 113 reviews

The exterior of the condominium building is showcased, featuring three levels with large windows that allow natural light in. A central staircase leads to the entrance, flanked by green grass and small shrubs, creating a welcoming appearance.

Apartment in Stratton

Great 2 bedroom condo at Stratton Mountain

4.94 out of 5 average rating, 104 reviews

A spacious living area features a large sectional sofa adorned with decorative cushions. A wooden coffee table sits in front, with a lamp beside it. A dining area is visible, accompanied by a window allowing ample natural light and a view of the surrounding trees.

Apartment in Dover

Cozy Mt Snow Ski In / Out

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, 155 reviews

Cozy Mountain Condo

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, 172 reviews

Modern Killington Farmhouse Condo: Close to Resort

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.