House holiday rentals in Wardsboro

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, 240 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)

A warm living space is highlighted by a stone fireplace, wooden walls, and large windows that frame the surrounding trees. The area features a cozy couch with a throw blanket, a rustic dining table, and multiple black dining chairs, creating an inviting atmosphere.

4.96 out of 5 average rating, 117 reviews

Hot Tub & Game Room - Ski Mt. Snow/Stratton

Nestled in the heart of Southern Vermont, our cozy and inviting home sits 10 min from Mt Snow and 15 min from Stratton, making it the ideal base for your adventure. Whether you're hitting the slopes, exploring hiking trails, or simply unwinding, you'll find everything you need for a memorable stay. Soak under the stars in our 7-person hot tub or cozy up inside for a night of relaxation. Discover the charm of Vermont and visit local breweries, farm-to-table restaurants, farms, and quaint towns.

4.94 out of 5 average rating, 160 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

Summit View Chalet @ Stratton is the ideal VT retreat, Minutes from Manchester, directly across the entrance from Stratton's 27 Hole Championship Golf Course. Beautifully remodeled! Relax in the hot tub on the deck with direct summit views in any season. Enjoy shuttle access to lifts, minutes from snowmobiling, hiking, fine dining and shopping. Comfortable accommodations for 6 adults and 5 children. Perfect for 2 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

4.93 out of 5 average rating, 421 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.

4.83 out of 5 average rating, 110 reviews

A charming yellow house is nestled among snow-covered trees, framed by tall evergreens. A snow-blanketed driveway leads up to the entrance, inviting visitors into a serene winter retreat in a wooded setting.

Home in Stratton

Stay mins from Mt. Snow & Stratton w/ EV charger

Enjoy the ultimate ski getaway in this private home that sits on 1 acre of beautiful wooded land. Park your car in the detached garage (w/Tesla charger). The spacious house comfortably sleeps 8 guests and sits between Stratton Mountain and Mount Snow with hiking trails and lakes just minutes away. Sit outside on the deck to enjoy serene views, warm sunshine and sounds of nature. Leave your worries and just relax, BBQ and enjoy the fire pit for cozy evenings with friends & family.

4.99 out of 5 average rating, 342 reviews

The exterior of a charming house features a gabled roof and a welcoming front porch with a wooden rocking chair. Lush green grass surrounds the home, and neatly trimmed shrubs are visible, complemented by tall trees in the background against a partly cloudy sky.

Home in Bennington

Southern Vermont Home

Beautiful home that offers privacy on over one acre of land. It is only a short drive to the conveniences of downtown shopping, restaurants, Bennington College, and much more. This house is 35 minutes from Manchester's famous outlets, 20 minutes from Williamstown, MA, and 45 minutes from Albany, NY. Bromley and Mount Snow ski areas are 40 minutes. The home has wonderful finishes and you will feel right at home upon arrival. Please come explore Vermont from our country escape!

4.86 out of 5 average rating, 111 reviews

A spacious living area features a large area rug centered on natural wood flooring, with large windows allowing ample natural light. Two sectional sofas are arranged around a coffee table, creating an inviting space to relax. A stone fireplace is positioned to one side, providing a rustic touch.

Home in Windham

The Architect's Cabin, on 10 Secluded Acres

Nestled on a rise in a woodland clearing is this intriguing cubist design reminiscent of Post and Beam ambiance. Stone and wood materials from the property have been assimilated into intriguing modern design features throughout. Walls of windows share the tranquil and private outdoor setting with the indoor livings areas. We only accept Instant Bookings, which require a verified account and positive host reviews. There is no Air Conditioning.

4.98 out of 5 average rating, 405 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

Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.

4.93 out of 5 average rating, 116 reviews

The contemporary cabin features an elevated design with wooden walls and large glass windows. A spacious porch includes seating for relaxation. The surrounding grassy area is complemented by natural landscaping, with fire pit seating visible in the background.

Home in Jamaica

The Post Haus: one-of-a-kind modern VT experience

Welcome to The Post Haus! A one-of-a kind, modern Vermont mini cabin in the Green Mountain National Forest. This high-end, mid-century mod getaway offers an indoor wood-burning fireplace, sauna, high-end kitchen, and two acres alongside the beautiful Ball Mountain Brook. Come enjoy our truly special piece of Vermont! Pets welcome with a $100 pet fee.

4.87 out of 5 average rating, 186 reviews

A single-story house features a light grey exterior with white trim and a welcoming front door. Flanking the door is a stone walkway leading to a grassy yard, where two white adirondack chairs are positioned. A small flowerpot adds a touch of color near the entrance.

Home in Shaftsbury

Cheerful 1 bedroom cottage

Located one mile from the historic village of North Bennington, this newly renovated one bedroom, one bath (with full kitchen) affords all the comforts of home while providing easy access to both Bennington College (within two miles) and the many attractions of the surrounding area.

4.94 out of 5 average rating, 192 reviews

A two-story house is nestled among lush greenery, framed by large trees. A stone wall borders the front yard, which features a natural landscape. The house displays a light exterior, with windows that invite natural light into the interior spaces.

Home in Newfane

Adorable home in Newfane

3 bedroom, 1 bath home. Fully equipped kitchen, cable and internet access. Pastoral meadow view. Quiet road. Private back yard with patio. Bordering on town forest. Close to popular swimming holes. 25 minutes to Mt. Snow, 15-18 to Brattleboro and Putney

Popular amenities for Wardsboro house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The open living area features a spacious green sofa with decorative pillows, facing a rustic wooden coffee table. Natural light illuminates the space, highlighting the vaulted ceilings and a cozy, inviting atmosphere. A breakfast bar can be seen in the background along with the kitchen area.

5 out of 5 average rating, 70 reviews

Stratton/Mt Snow minutes away! Hot tub + Game room

5 out of 5 average rating, 25 reviews

MtSnow/Stratton Ski Lodge-Hot Tub-Game Room-Pool

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"

4.93 out of 5 average rating, 229 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

5 out of 5 average rating, 21 reviews

A charming house is nestled among greenery, featuring a screened-in porch with a red door. Low shrubs and flowering trees frame the entrance. Soft light filters through the trees, highlighting the natural surroundings and offering a sense of tranquility.

Home in Dummerston

Woodsy Retreat with Private Pool

4.98 out of 5 average rating, 62 reviews

The spacious living room features a large, sectional grey couch and a white armchair, arranged around a wooden coffee table. A brick wood-burning fireplace is situated against a wooden wall, with a mounted TV above it. The room is illuminated by warm lighting.

Home in Dover

Winter Skiing @ Mt Snow! Ski off trail sleeps 8.

Wander In | Close to Mount Snow & Stratton

4.89 out of 5 average rating, 228 reviews

A pathway lined with lush greenery leads to a bungalow with a screened-in porch, featuring outdoor seating. The soft sunlight filters through the foliage, creating a serene entrance to the welcoming space.

Home in Williamstown

Hollywood Bungalow in the Berkshires #C0191633410

Weekly house rentals

A charming, blue house nestled among snow-covered trees showcases an inviting entrance with wooden steps leading up to a deck. A festive star and decorative elements adorn the exterior, while fresh snowfall blankets the surrounding landscape, creating a serene winter scene.

The Castle

A single-story chalet is nestled among trees, featuring a light green exterior with white trim. Large windows allow natural light into the living space, while a decorative element mimics the shape of a window above the entrance. Colorful plants adorn the entrance, surrounded by grassy land.

4.94 out of 5 average rating, 47 reviews

Riverside Chalet near Mt. Snow & Stratton resorts

A large hot tub is seen illuminated in blue light, positioned on a deck surrounded by a serene wooded area. String lights overhead create a gentle ambiance, with outdoor seating visible in the background, inviting relaxation in a peaceful setting.

5 out of 5 average rating, 23 reviews

Mountain house w/ large hot tub

5 out of 5 average rating, 63 reviews

An open living area features vaulted ceilings and large windows, allowing natural light to fill the space. A comfortable leather sofa sits adjacent to a dining table, with views of the surrounding greenery visible outside. A spacious kitchen island adds functionality to the layout.

Home in East Dover

Magical Retreat Cottage Autumn Colors & Waterfalls

A tranquil view of a swimming pond is reflected among lush greenery and blooming wildflowers. A charming house with a light green exterior is visible in the background, framed by vibrant trees and a partly cloudy sky.

4.85 out of 5 average rating, 41 reviews

Cozy mountain getaway between Mt. Snow&Stratton

A historic red farmhouse is partially visible, surrounded by a blanket of fresh snow. Snow-covered mounds can be seen below a mature tree, which stands prominently near the house. The cloudy sky adds a serene ambiance to the winter scene.

4.8 out of 5 average rating, 64 reviews

Fairview Farmhouse. Rambling, cozy 1800s hideaway

4.93 out of 5 average rating, 15 reviews

Home in Townshend

Historic Riverfront 3BR Farmhouse, Pet-Friendly

5 out of 5 average rating, 13 reviews

Home in Brattleboro

1840 cottage

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

4.71 out of 5 average rating, 38 reviews

A cozy living area features a comfortable sofa and two armchairs arranged around a circular wooden coffee table. Large floor-to-ceiling windows allow natural light to illuminate the space, providing views of the lush greenery outside. Exposed wooden beams enhance the room's character.

Home in Sunderland

Modern, Serene Farmhouse Retreat

Home in Dover

Private Chalet - 4 mins to Mt Snow

5 out of 5 average rating, 93 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

The Vermont Farmhouse+Ski Bromley+Dog Friendly

4.99 out of 5 average rating, 76 reviews

The exterior of a charming converted carriage house is showcased, featuring a mix of wood and siding. Lush greenery surrounds the structure, with colorful flower pots placed along the pathway leading to the entrance. A gravel driveway and mature trees add to the serene atmosphere.

Home in Dorset

Home in the Heart of Dorset Village

Mt Snow/Stratton Cozy Ski Cottage with river views

4.89 out of 5 average rating, 19 reviews

A modern wooden structure is situated on a grassy area, surrounded by vibrant autumn foliage. The large windows reflect the natural light and provide a view of the colorful trees in the background, emphasizing the serene woodland setting.

Home in Newfane

Relaxing Mountain Retreat with a View