House vacation rentals in Chester

4.94 out of 5 average rating, 98 reviews

A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.

Home in Guilford

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

4.96 out of 5 average rating, 129 reviews

A gently sloping field is depicted, bordered by trees with autumn foliage. A red barn and a white building are visible in the distance, set against a bright blue sky with scattered clouds. The landscape conveys a peaceful rural setting.

Home in Townshend

Lawrence Cottage

Deep in the West River Valley region of Windham County, Lawrence Cottage is in a gorgeous and uncluttered setting upon Windham Hill. If you long for solitude, serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

4.9 out of 5 average rating, 245 reviews

An open concept living space features four arched windows that allow ample natural light. Wooden floors complement the revealed post and beam construction. A wooden dining table is centrally placed, with a cozy seating area in a corner, creating a relaxed environment.

Home in Putney

Spacious Loft with View

Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

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.

4.91 out of 5 average rating, 113 reviews

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!

4.91 out of 5 average rating, 117 reviews

Home in Ludlow

The Bluebird Day Chalet 2 bed dtwn Ludlow Village

Cozy heart of Ludlow Village location on the shuttle route (free!) for Okemo & close to Echo Lake that sleeps 6. As downtown as possible! Okemo shuttle stop at The Mill. Quick walk to good eats & drinks (Downtown Grocery, Stemwinder, Main + Mountain, etc.), Shaws, Rite Aid, and The Wine & Cheese Shop (perfect for après ski!). On site parking for 2 cars & free on street parking if needed (no overnight). Wifi & smartTV to stream your favorites while you relax after a long day on the slopes.

4.93 out of 5 average rating, 424 reviews

A rustic building with wooden siding is partially surrounded by a foggy landscape. An elevated deck with rocking chairs invites relaxation. The entrance features glass doors flanked by large windows, allowing natural light to illuminate the interior. Surrounding greenery creates a serene atmosphere.

Home in Putney

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

4.94 out of 5 average rating, 311 reviews

Home in Winhall

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

4.99 out of 5 average rating, 123 reviews

Adirondack chairs and a small side table are positioned on a spacious deck, offering an unobstructed view of Okemo resort. The winter landscape features snow-covered ground, complemented by a clear blue sky and distant mountain views.

Home in Ludlow

Stunning Okemo Views - 3BD 3BA on 10 Private Acres

Recently constructed on ten private acres with captivating views of Okemo. Three BR, three full bath, air conditioned modern chalet, just 1.5 miles from downtown and 3 miles from Okemo’s base areas. Epic views of Okemo and surrounding mountains from every room. Cozy around the fireplace in the living room or enjoy smores outside by the firepit, or unwind on the deck. Lower level has second living room great for kids with large TV, comfy couches, Pac Man arcade, foosball and board games.

4.98 out of 5 average rating, 102 reviews

A spacious kitchen and dining area features a wooden table surrounded by chairs, with a decorative table runner. Stainless steel appliances, including a refrigerator and microwave, create a modern look. Large windows allow natural light to fill the room, providing views of the outdoor scenery.

Home in Charlestown

Private & Cozy Farmhouse in New Hampshire

Escape to our relaxing farmhouse in a quiet corner of Charlestown, NH. Overlooking farm fields, old barns and the Connecticut River, this property is the perfect quiet getaway! The house is within walking distance of the river as well as downtown Charlestown. It is located between Claremont, NH and Keene, NH making it a great midway point to access both for shopping, area attractions and a number of ski resorts. Minutes from I-91. Come and make yourself at home in this private getaway!

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.

4.98 out of 5 average rating, 165 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.

A rustic cabin is nestled among vibrant wildflowers and lush greenery. A variety of flowers, including purple and yellow blooms, frame the scene, leading the eye towards the charming structure with a classic metal roof and wooden accents.

4.98 out of 5 average rating, 219 reviews

Meadow View. 35 acres outside your door!

Meadow View - pet friendly home away from home. 35 acres- including 2 trout ponds and 25 acres of wooded trails (perfect for hiking, cross country skiing/snow shoeing!). Featuring a newly remodeled kitchen and bathroom. Minutes from Mt. Ascutney (trails galore, rope tow in the winter). The unit is perfect spot for couples craving time in rural Vermont or for families/outdoor enthusiasts who want to go mountain biking, skiing, hiking. (Okemo 30 min Killington 45 min)

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.

4.97 out of 5 average rating, 115 reviews

Vermont 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.

Popular amenities for Chester house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

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

4.9 out of 5 average rating, 230 reviews

Luxury Condo Tucked in the Heart of Killington

4.91 out of 5 average rating, 105 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

Ski home to Trail Creek!

4.88 out of 5 average rating, 263 reviews

The exterior of a cozy ranch house is shown, framed by lush greenery and flowering shrubs. The front porch is accessible via steps, with a teal door welcoming visitors. A pathway leads through the manicured lawn, enhancing the inviting appearance of the property.

Home in Mendon

Ranch at Mendon Mt Orchards

4.88 out of 5 average rating, 180 reviews

A comfortable living area features a sectional gray sofa adorned with decorative pillows, a coffee table at the center, and two armchairs. Natural light filters in through large windows dressed in light curtains, illuminating the hardwood floor and creating a cozy atmosphere.

Home in Wilmington

Adams Farm-"The Little Farmhouse"

4.99 out of 5 average rating, 147 reviews

A spacious living room is illuminated by large windows overlooking the forest. A leather sofa and armchair are arranged around a patterned area rug. A coffee table and side table with modern lamps complete the cozy seating area. A wood-burning fireplace adds warmth to the setting.

Home in Killington

SugarBear- Pool, Hot Tub, 2 En Suites BR

4.93 out of 5 average rating, 230 reviews

A Colonial home is positioned on a green lawn, showcasing a charming brick façade and a classic porch. Large trees provide shade, while an American flag is displayed proudly by the door. Nearby, a design studio is visible, highlighting the spacious front yard.

Home in Keene

The Brick House on Washington Street

4.92 out of 5 average rating, 109 reviews

The spacious great room features a wood-burning fireplace and is furnished with two comfortable sofas and a wooden coffee table. A large flat-screen TV hangs on the wall, and natural light emanates from the surrounding windows. A dining area with a circular table is visible in the background.

Home in Ludlow

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

4.9 out of 5 average rating, 148 reviews

The exterior of a charming yellow house is surrounded by lush greenery and colorful landscaping. A stone pathway leads to the entrance, framed by well-maintained shrubs and ornamental features. Tall trees provide privacy and a natural backdrop, enhancing the serene outdoor atmosphere.

Home in Plainfield

Historic Home on 17 acres of land. Go escape!

Weekly house rentals

5 out of 5 average rating, 69 reviews

The living area features a spacious sofa and armchair, framed by large windows that provide ample natural light. Exposed wooden beams run along the ceiling. A decorative rug adds color to the hardwood floor, and a mantelpiece serves as a focal point in the room.

Home in Tinmouth

Charming Vermont Schoolhouse

The living room features a large sectional sofa positioned toward a TV stand, providing ample seating. A ceiling fan is installed above, and large windows allow natural light to fill the space. A coffee table rests in the center, while a dining area is visible through an adjacent room.

4.93 out of 5 average rating, 15 reviews

Bright and spacious 3 bed/3 bath

4.96 out of 5 average rating, 80 reviews

A charming two-story house with a yellow front door is set against a lush green lawn. Vibrant flowers bloom in the foreground, adding color to the landscape, while trees provide natural shade around the property.

Home in Springfield

Charming New England Cape

An outdoor space features a fire pit surrounded by four seating options, including two blue adirondack chairs and two black metal chairs. The area is set on a gravel surface with fallen leaves, complemented by a background of a blue farmhouse and trees.

4.85 out of 5 average rating, 47 reviews

Historic 150-Year-Old Farmhouse | Jacuzzi included

5 out of 5 average rating, 36 reviews

Home in Springfield

Scandinavian Serenity Close to Okemo

The exterior of a two-story wooden house is displayed, surrounded by lush greenery. A porch with green railings wraps around the building, and vibrant pink flowers are seen in a wooden barrel planter at the forefront, adding a touch of color to the serene landscape.

5 out of 5 average rating, 7 reviews

Remington Ridge

A charming yellow farmhouse is framed by lush greenery, highlighting its welcoming entrance. The front porch is accentuated by steps leading to the door, with multiple windows allowing natural light to fill the interior. A gravel path guides visitors to the home.

5 out of 5 average rating, 9 reviews

Quaint Farmhouse

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.

5 out of 5 average rating, 94 reviews

Historic Mill • Near Okemo • Fireplaces • Wi-Fi

Private house rentals

4.86 out of 5 average rating, 14 reviews

An open living space features large windows that allow ample natural light, revealing snow-covered grounds outside. A cozy sofa is adorned with decorative pillows and a throw. A rustic coffee table and an area rug add warmth, while the kitchen area is visible in the background.

Home in Londonderry

Bright & Vibrant Mountain Home

5 out of 5 average rating, 31 reviews

Home in Jamaica

Tranquil VT Ski House Retreat

5 out of 5 average rating, 69 reviews

The living room showcases vaulted wooden ceilings and large windows offering expansive views of the outdoors. A cozy seating arrangement is positioned around a central coffee table, with warm lighting provided by a chandelier. Natural light fills the space, enhancing the welcoming ambiance.

Home in Andover

Luxury VT Retreat. Breathtaking Views & Sunsets

The duplex farmhouse is surrounded by a spacious yard, featuring a mix of grass and patches of snow. Large trees provide shade, and the building shows a traditional design with multiple windows and a welcoming entryway. A distant barn is visible beyond the farmhouse.

5 out of 5 average rating, 26 reviews

Elm Gate Farm

5 out of 5 average rating, 99 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!

Superhost

A snow-covered landscape surrounds the historic farmhouse and attached barn. The yellow house features a rounded wall and is partially obscured by snowdrifts. The red barn is visible to the right, under a clear blue sky, creating a serene winter scene.

4.8 out of 5 average rating, 94 reviews

Vermont 1828 Reunion House, near Okemo

4.97 out of 5 average rating, 69 reviews

Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain

A spacious country manor is depicted, with a gray exterior and multiple windows. The property's expansive lawn is framed by colorful autumn foliage, offering hints of vibrant reds and yellows. A gravel driveway leads to a two-car garage on the right side.