House holiday rentals in Stratton

4.94 out of 5 average rating, 132 reviews

A spacious living room features a vaulted ceiling and an arched window that allows natural light to flood the space. Comfortable seating arrangements include two red sofas and a patterned area rug. Shelving units display decorative items, while a media system is positioned above the fireplace.

Home in Brattleboro

Modern Spacious Home with Mountain Views

Modern Home in Brattleboro with mountain view & many extras: Italian-Marble master-suite, Jacuzzi/Shower for 2, walk-in closet, king bed, grill, heated garage, cable, WiFi. Open-concept living room w/ cathedral ceiling, office, & movie screen. Large open kitchen w/ wine fridge. Second bedroom w/ loft. Explore hiking trails from backyard. Pets ok! 3 mins from Vermont Country Deli & I91 Exit 2. Walking distance to dog park, swimming holes. Downtown: 4 mins Mount Snow: 40 mins Stratton: 54 mins

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.

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, 119 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.

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.

4.95 out of 5 average rating, 164 reviews

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!

A modern interior is showcased with wooden walls and flooring, featuring a cozy bed positioned near large windows. A compact dining area is visible, with a small table and two chairs. An air conditioning unit is installed on the wall, contributing to the space's comfort.

4.94 out of 5 average rating, 308 reviews

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, 122 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.

4.86 out of 5 average rating, 301 reviews

Home in Jamaica

Yellow Sweetie at the Base of Stratton

Our adorable home, The Yellow Sweetie, is located in a convenient setting at the base of Stratton Mountain, just 1 minute to the Stratton Resort access road and 8 mins to the slopes. Explore Vermont's many historic towns with classic architecture and covered bridges, as well as its breathtaking mountains, rivers and lakes. The Yellow Sweetie offers stylish country living-meets-shabby chic comfort and coziness. Escape to the fresh Vermont mountain air where life feels a little bit simpler!

4.83 out of 5 average rating, 111 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.

A cozy living area features a large sectional sofa adorned with decorative cushions. A wooden coffee table sits in the center, surrounded by an area rug. A stone fireplace with a fire is visible, enhancing the space's comfort, and a staircase leads to the upper level.

4.98 out of 5 average rating, 131 reviews

3BR 2BA Stratton Condo w/ Fireplace & Forest Views

Newley renovated 3 bed 2 full bath condo on Stratton, just minutes to Stratton's base lodge. Kitchen is well equipped for cooking. Private balcony with forest views. All new appliances. Wood burning fireplace & firewood included. All beds & baths are on 2nd floor up spiral staircase which may be difficult for elderly or young children. Stairs are required. Master bed has en suite full bath and smart tv. Free parking. Living room has an 86" smart TV. Poker set, & board games.

4.93 out of 5 average rating, 134 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.

If you are looking for a cozy spot to relax in a small town, with fast internet and easy access to lots of fun activities, this house is it! On the main floor of the house, there is an open layout that includes a library, a small bar, a dining room, a kitchen, a bathroom, and two bedrooms. Downstairs, there is a finished basement that includes a large family area with a huge couch (perfect for movies), a workspace, and a laundry space. Private parking and lots of outdoor space.

4.77 out of 5 average rating, 230 reviews

A sunroom is featured with large windows allowing natural light to fill the space. Wooden furniture adds a warm touch, while a woven rug covers the floor. A small side table is positioned next to a seating area, overlooking a green landscape outside.

Home in Manchester

The Equinox Cottage

The Equinox Cottage is a quick 3 minute drive to the Equinox Hotel and the heart of Historic Manchester Village. Enjoy the shops, outlets, restaurants, cafes, golfing, and relaxed summer vibe. The Cottage is also an easy walk to the trails in the Equinox Pond preserve. Enjoy this pristine wilderness oasis, plus hiking up Equinox Mountain and surrounding trail system without having to step into your car. This peaceful, spacious, serene spot is ideal for summer relaxation.

4.88 out of 5 average rating, 259 reviews

An open dining area features a large wooden table surrounded by white chairs. Natural light fills the space from multiple windows, highlighting rustic wooden beams above. A cozy seating nook with plants and a decorative fireplace creates a welcoming ambiance.

Home in Dover

Mt Snow retreat, ski & summer

Warm and welcoming space for relaxation and play, your home base for VT recreation. 7 min. drive to Mount Snow, convenient location. Easy access to hiking, mountain biking, x-c skiing, golf course, and more! Sleeps 5 easily. ~10 min. walk to Moover, 7-11, restaurants. INTERNET - There is a fiber optic connection and the plan speed is 50Mbps down / 30Mbps up. LGBTQ+ friendly 🌈💞

Popular amenities for house rentals in Stratton

Kitchen

Wifi

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, 71 reviews

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

4.98 out of 5 average rating, 203 reviews

The classic two-story farmhouse features white siding with black shutters. A green door welcomes visitors, while lush greenery and blooming lilac bushes create a natural frame. The surrounding lawn is expansive, emphasizing the peaceful rural setting.

Home in Salem

Magical Farm Getaway - a must visit!

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.

4.88 out of 5 average rating, 180 reviews

Adams Farm-"The Little Farmhouse"

4.92 out of 5 average rating, 107 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!

5 out of 5 average rating, 11 reviews

Wander In | Close to Mount Snow & Stratton

4.93 out of 5 average rating, 117 reviews

The historic farmhouse is presented with a classic white exterior and black shutters. A spacious wraparound porch offers several seating areas. Lush green grass and neatly trimmed shrubs surround the building, enhancing the inviting appearance against a clear blue sky.

Home in Granville

Historic 1850’s Renovated Farmhouse w/ Pool!

4.9 out of 5 average rating, 229 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

5 out of 5 average rating, 3 reviews

Home in Dorset

Bright home w/ firepit & resort access

5 out of 5 average rating, 13 reviews

The spacious kitchen features a large island with seating for six and modern appliances. Natural light fills the room through a wide window, and warm wood paneling creates a welcoming atmosphere. An open layout connects the kitchen to a dining area equipped with wooden tables and chairs.

Home in Stratton

New Build Ski Home 10 Min to Stratton & Mount Snow

5 out of 5 average rating, 26 reviews

A modern mountain house is framed by snow-covered trees, showcasing tall windows and a sloped roof. Soft lights illuminate the interior, revealing a cozy space. A covered porch with seating is visible at the front, along with a snow-dusted vehicle parked nearby.

Home in Peru

Highland Haus: stunning ski getaway with hot tub

The exterior of a two-story house is shown, featuring a dark grey facade and multiple large windows that provide natural light. A wooden deck with steps leads to the front door, flanked by snowy terrain and bare trees, creating a calm winter atmosphere.

4.96 out of 5 average rating, 25 reviews

Mountain House between Stratton, Bromley, Magic

5 out of 5 average rating, 36 reviews

Home in Springfield

Scandinavian Serenity Close to Okemo

4.94 out of 5 average rating, 97 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

5 out of 5 average rating, 33 reviews

The exterior of a modern A-frame house is displayed, featuring a distinctive triangular roofline. A spacious deck is visible, complemented by outdoor seating. The surrounding foliage suggests a serene natural environment, with pumpkins adorning the entrance and vibrant autumn leaves scattered on the ground.

Home in Jamaica

Cozy A-frame Ski Getaway

5 out of 5 average rating, 5 reviews

A-Frame | Hot Tub| Dog Friendly | Near Mt. Snow

Private house rentals

A stone fireplace serves as a focal point in the living area, featuring a sturdy wooden mantle. Flanking the fireplace, built-in shelves showcase decorative plants and curated items. A cozy sofa sits nearby, accompanied by a wooden coffee table atop a textured rug.

4.95 out of 5 average rating, 22 reviews

Entire Chalet in Winhall, Vermont

A spacious living area features a large sectional sofa in front of a flat-screen TV. Natural wood walls and ceilings create a warm ambiance. Dining seats are visible in the background, set near large windows that allow natural light to enhance the room.

4.9 out of 5 average rating, 73 reviews

Mt Snow/Stratton Getaway-TESLA Charger

5 out of 5 average rating, 47 reviews

Home in Dover

Briar Ridge - Beautiful 4 Bedroom Ski Home

4.96 out of 5 average rating, 72 reviews

The kitchen features light green cabinetry and a spacious island with a wooden herringbone countertop. Equipped with stainless steel appliances, a skylight allows natural light to brighten the area. Open shelves display plants and dishware, enhancing the kitchen's functionality.

Home in Manchester

Gather and Relax with Friends & Family

A welcoming sign featuring 'Welcome to Boulder House, Wilmington, VT' hangs above a wooden surface. Below the sign, a collection of eight wine glasses and a glass decanter are arranged, reflecting a simple yet elegant presentation.

4.95 out of 5 average rating, 77 reviews

Boulder House

5 out of 5 average rating, 22 reviews

A bright and spacious living area is presented, featuring a comfortable gray sofa set against wooden flooring. A work-from-home station is positioned by large windows overlooking the outdoors. Natural light floods the room, complemented by ceiling fans and light-colored walls.

Home in Stratton

Beautiful 3-4 BR, 2 Ba, Sleeps 9

A charming cottage features a well-maintained exterior with white siding and a dark shingle roof. A large deck is accessible from the front, complemented by a welcoming entryway. American flags gently adorn the porch, surrounded by a grassy area with trees in the background.

5 out of 5 average rating, 9 reviews

Stowe Hill Cottage. Min's to Lake and Mt Snow

A fire pit surrounded by smooth stones sits at the center of the outdoor space, with a warm flame rising in the evening light. Two Adirondack chairs are positioned nearby, illuminated by soft string lights overhead, enhancing the natural setting surrounded by trees.