Pet-friendly holiday rentals in Winhall

4.99 out of 5 average rating, 186 reviews

Chalet in Stratton

7 Min Stratton Mtn/15 Min Mt Snow /Wood Fireplace!

Cozy chalet awaits your stay. This home sits on just under 4 acres. Sit back & enjoy the heated sunroom and stare out at the woods that surround you. You may be lucky enough to spot one of the moose or bear that visit the property. Kitchen remodeled 2023! Open floor plan w/wood burning fireplace. Main bedroom has new King Bed & twin bunks. Finished basement with new Queen size bed & twin bunk above. Kid friendly home! Mins to Stratton Mtn & Mt Snow for skiing & golf! Free Disc golf on property.

4.88 out of 5 average rating, 149 reviews

A charming treehouse is nestled in a snowy landscape, elevated on stilts with a wraparound deck. Soft white lights illuminate the exterior, while snow gently falls around it. A wooden staircase leads up to the entrance, highlighting the inviting ambiance.

Treehouse in Londonderry

Riverbed Treehouse @hot tub & a new sauna & views!

The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

A rustic cabin built on stilts is surrounded by snow-covered ground and tall trees. The structure features a pitched roof and a spacious deck. Sunlight filters through the branches, casting shadows on the snow, highlighting the natural beauty of the winter landscape.

4.89 out of 5 average rating, 100 reviews

Chic Cabin with Fireplace at Stratton Mountain

Originally built as a corn crib in the 1800s, this 2 bedroom, two bath cabin has been lovingly maintained and features many original details from wide pine floors to a brick fireplace. This beautiful post and beam cabin is nestled in the Green Mountains of Central Vermont with convenient access to some of the best skiing, hiking, & sightseeing: 10 min to Stratton Mountain and Bromley, 15 min to Manchester, 20 min to Magic Mountain, 30 min to Mount Snow, 40 min to Okemo, and 1 hour to Killington

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A cozy bedroom features a metal bed frame adorned with a colorful quilt. Soft pillows are arranged at the head of the bed, and a bedside lamp provides gentle illumination. An angled ceiling creates an intimate atmosphere, complemented by a framed landscape picture on the wall.

Guesthouse in Manchester

4.75 out of 5 average rating, 289 reviews

Romantic Barn Guesthouse in Village Center

Keep it simple at our peaceful and centrally-located hideaway. This rustic and cozy two-story barn guesthouse with fireplace is located on four acres of a 1768 historic homestead right in Manchester Center. Enjoy the pond and mountain views from the bedroom and living room windows; the guesthouse faces a peaceful meadow and wildlife pond which abuts 70 acres of preserved land with hiking trails, yet it's also just steps from Main Street and all of the dining and shopping of Manchester Village.

4.95 out of 5 average rating, 168 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!

The cabin is nestled among vibrant autumn foliage, showcasing a blend of orange, yellow, and green leaves. A gravel driveway leads up to the chalet-style house, featuring large windows that invite natural light. Surrounded by trees, the setting offers a serene retreat.

4.91 out of 5 average rating, 160 reviews

Snow Valley Cabin-Cozy Escape Near Skiing & Nature

The Snow Valley Cabin is a three bed one-and-a-half bath chalet-style house designed for your perfect Vermont getaway. Wooden vaulted ceilings, wood-burning fireplace, beautiful view of the snow-capped Bromley mountain, and Scandinavian style details. We are conveniently located on the edge of the Green Mountain Forest just 4 miles from Bromley, 9 miles from Stratton, 14 miles from Magic, and 12 minutes to Manchester. Stay here to relax and wind down with friends and family, and even pets!

Superhost

Home in Jamaica

4.86 out of 5 average rating, 304 reviews

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!

5 out of 5 average rating, 207 reviews

The cabin features a wooden exterior surrounded by lush greenery, with large windows allowing natural light to enter. A wooden deck extends from the side, leading to a cozy outdoor area and an adjacent structure, contributing to the rustic charm of the setting.

Tiny home in Dover

Rustic Cabin in foothills of Green Mountains

Rennsli Cabin is off grid + nestled on a forested plateau in the foothills of the Green Mountains. You will feel like you are in the middle of nowhere, unplugged and able to regenerate. Kitchen is equipped with cooking essentials, water, coffee, tea, milk, fresh eggs + homemade soap. It has an indoor compost toilet, outhouse + outdoor shower (May-Oct) Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

4.84 out of 5 average rating, 591 reviews

A cozy cabin is nestled in a snow-covered landscape, featuring a blue hammock hanging from the porch. Snowflakes gently fall around a dog wearing a blue coat, playing in the deep snow in front of the entrance. Wooden stools are positioned near the entrance.

Cottage in Jamaica

Cottage-7 min to Ski Stratton-Woodstove-View-DogOK

Authentic post & beam cottage surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Nearby swimming hole at brook on property. Fire pit, propane BBQ, picnic table, spectacular Stratton Mountain view. Front porch & back porch with hammock, table & chairs. VCR/DVD & videos, boardgames & puzzles, kids toys, turntable & records, Satellite Internet & WiFi 20-100 mbps, TV & Roku. Gas heat, wood stove. Dog friendly.

4.96 out of 5 average rating, 369 reviews

Dog Friendly A-Frame Retreat near Hiking, Skiing

The Vermont A-Frame is a dog friendly cabin conveniently located on the edge of the Green Mountain Forest. WFH using our fast WiFi + enjoy nature while doing so! Whether your plan is to ski, shop, hike or just relax, the Vermont A-Frame is the ideal place to experience it all. With room for 4 and plenty of amenities, our charming A-Frame is sure to provide you with the perfect home for your Vermont vacation. Find us on social media! @thevermontaframe

4.98 out of 5 average rating, 458 reviews

A bright interior is featured, showcasing a mix of seating options including a blue sofa and an upholstered armchair. A small dining table is complemented by wooden chairs. The kitchen area is visible, equipped with diverse utensils, while large windows on two sides allow natural light to fill the space.

Apartment in Andover

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

4.93 out of 5 average rating, 121 reviews

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.

Popular amenities for Winhall pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.97 out of 5 average rating, 127 reviews

A spacious bedroom is illuminated by natural light from multiple windows. A large bed with patterned linens is centered on a wooden floor. A simple chair and framed artwork add to the room's welcoming ambiance, complemented by warm wall tones and soft area rugs.

Home in Manchester

Modern meets Country Cottage in Manchester Village

4.99 out of 5 average rating, 151 reviews

An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.

Home in Londonderry

Modern 3-bedroom A-frame in Londonderry w/ Pond

4.96 out of 5 average rating, 165 reviews

A charming white farmhouse is surrounded by lush green trees, showcasing a covered front porch with rocking chairs. An American flag gently waves, complementing the inviting exterior. Sunlight casts a soft glow on the natural landscape, creating a serene and peaceful setting.

Home in Grafton

Ephriam Bruce House- ON RIVER IN VILLAGE CENTER

4.96 out of 5 average rating, 248 reviews

A wide view of colorful autumn foliage is captured, showcasing a variety of trees with hues of red, orange, and yellow. A clear blue sky sets a backdrop against the distant mountains, creating a serene landscape.

Home in Danby

Comfortable farmhouse with stunning views

4.97 out of 5 average rating, 157 reviews

A dining area is highlighted by a wooden table set for four, surrounded by light green chairs. Natural light fills the space through two large windows, while a vintage hutch displays colorful items against a contrasting gray wall.

Home in Londonderry

Wild Blossom Farmhouse - a lovely family getaway

4.9 out of 5 average rating, 104 reviews

A comfortable living area features a sectional sofa adorned with soft pillows and a wooden coffee table. Natural light floods in through a large window, highlighting the wooden wall paneling. A decorative rug rests under the table, adding warmth to the space.

Home in Dorset

Mountain View Getaway

4.94 out of 5 average rating, 135 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

4.93 out of 5 average rating, 139 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.

Pet-friendly home rentals with a pool

4.92 out of 5 average rating, 211 reviews

A rustic log cabin is set amidst lush greenery, framed by tall trees. A covered porch extends along the front, providing space for seating. Natural stone steps lead up to the entrance, and a small fire pit is visible in the foreground, surrounded by stones.

Cabin in Wardsboro

Leonard’s Log - Private Hot Tub, Fire Pit, A/C

4.91 out of 5 average rating, 961 reviews

The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.

Guesthouse in Granville

Moon Valley Country Retreat no clean fee pets yes

4.98 out of 5 average rating, 167 reviews

A red wooden cabin nestled among trees, showcasing a welcoming front porch. Air conditioning units are situated to the side. Natural light filters through the foliage, creating a serene and shaded outdoor atmosphere.

Barn in Newfane

Beautiful rustic woods and fields retreat.

4.99 out of 5 average rating, 267 reviews

Exposed wooden beams frame the room, complemented by warm brick walls. A cozy fireplace sits centered against the wall, with decorative art above it. A comfortable chair and lamp are positioned nearby, while a television and small dresser provide functional elements in the living space.

Cottage in Newfane

Cozy Vermont Antique Sugar House with Fireplace

4.88 out of 5 average rating, 229 reviews

A cozy interior space features a sleeping area with a rust-colored bedspread and wooden walls. A plush chair and a futon occupy the room, complemented by a soft rug underfoot. Soft lighting hangs from the ceiling, creating a warm ambiance.

Tiny home in Brattleboro

“Sugar Maple” Rustic 4x4 Cabin Getaway, Fireplace

5 out of 5 average rating, 117 reviews

A charming red chalet is nestled among snow-covered trees, complemented by a clear winter sky. Icicles hang from the roof, and a wooden deck is partially visible, showcasing the inviting entrance adorned with festive decor.

Chalet in Wilmington

Mt Snow Chalet: Peaceful Escape w/Hot Tub

4.9 out of 5 average rating, 230 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

4.88 out of 5 average rating, 120 reviews

Chalet in Winhall

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton

Private, pet-friendly home rentals

4.99 out of 5 average rating, 134 reviews

Cabin in Sunderland

The Birchwood Cabin - Stunning Mountain Views

4.92 out of 5 average rating, 215 reviews

A serene landscape of a tranquil pond reflects a historic red building surrounded by trees adorned with golden foliage. Gentle hills rise in the background, while the sky displays a mix of light and shadow, creating a peaceful atmosphere.

Cottage in Pawlet

The Smithy Cottage at Consider Bardwell Farm

4.96 out of 5 average rating, 28 reviews

A spacious kitchen includes a large central island with seating, stone countertops, and professional appliances. Warm light from decorative pendant fixtures illuminates the room. Natural light streams through several windows, highlighting flowers arranged on the counter and inviting a cheerful atmosphere.

Apartment in Manchester

Modern Mountain Retreat w/ Chef’s Kitchen

4.86 out of 5 average rating, 104 reviews

A two-story home is set against a bright blue sky, showcasing a snow-covered exterior. The front entrance features a staircase leading to a welcoming porch. Surrounding trees add a natural backdrop, while snow blankets the ground, highlighting the property's serene, wintry atmosphere.

Chalet in Jamaica

7min-Stratton Dogs OK Fire Pit EV Charger Arboreal

A spacious living room features high wood-paneled ceilings and large windows allowing natural light. Comfortable seating is arranged around a wooden coffee table on a soft area rug, with a stone fireplace as a focal point. A potted plant adds a touch of greenery.

4.96 out of 5 average rating, 79 reviews

Stylish Getaway w/ Hot Tub & Firepit Near Stratton

Superhost

Home in Winhall

4.88 out of 5 average rating, 24 reviews

Stratton; 8 min! Swimming, 2 min. Pet friendly

4.95 out of 5 average rating, 111 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.

Condo in Stratton

Great 2 bedroom condo at Stratton Mountain