Pet-friendly vacation rentals in Winhall

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Top-rated pet-friendly home rentals in Winhall

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favourite
The exterior of a two-story contemporary home is depicted, featuring green-framed windows and a pathway lined with gravel. Adjacent grassy areas and trees create a natural setting. A blue flag flutters near the entrance, enhancing the welcoming feel of the property.
Home in Weston
4.95 out of 5 average rating, 305 reviews

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

Guest favourite
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
4.85 out of 5 average rating, 107 reviews

7min-Stratton Dogs OK Fire Pit EV Charger Arboreal

7min drive to pickleball, tennis, pool, golf, mountain biking and skiing @Stratton Resort. Soak up 13 acres of arboreal views from your private chalet. Light-filled w/ southern exposure. Deck and fire pit for stargazing, mid-century modern furnishings, new appliances, and 300Mbps Wi-Fi and a Mini Split AC/Heat. Convenient to ski areas, restaurants, shops, and swimming holes, yet secluded and quiet. Walk to Pikes Falls 29min to Bromley and Mt Snow AWD required for spring/winter. Pet fee $187.

Top guest favourite
The log cabin is illuminated against the night sky, showcasing its rustic charm. Snow accumulates around the entrance and pathway, while warm light spills from the windows, creating a cozy atmosphere. The sloped roof features wooden beams, enhancing the cabin's unique design.
Cabin in Stratton
5 out of 5 average rating, 181 reviews

Log Cabin, King Beds & AC Near Hike/Swim/Golf/Bike

Kick back and relax in this calm, stylish, newly built log cabin which was finished in early 2022. Fully equipped with stainless steel appliances, soapstone counters, central a/c, all new furniture, mattresses and bedding. First floor master bedroom leads into a large, covered, screened in porch, which is perfect for your early morning coffee or evening cocktails. Starlink high speed Wi-Fi and a smart tv in the living room and bedroom. 7 Minutes from Stratton Mtn, 15 from Mt Snow. Nearby lakes!

Guest favourite
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.
Cabin in Winhall
4.88 out of 5 average rating, 104 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

Guest favourite
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, 292 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.

Guest favourite
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
4.95 out of 5 average rating, 168 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!

Superhost
A welcoming living area features a stone fireplace with a warm fire glowing inside. Wooden beams cross the ceiling, and a red couch is complemented by leather ottomans. A large window reveals a snowy outdoor setting, while a coffee table holds various items.
Home in Winhall
4.85 out of 5 average rating, 197 reviews

The Mushroom House of Manchester Vermont

Welcome to The Mushroom House. Located at the end of a private road, the house is less than 4 miles from Manchester's outlet shopping, gorgeous hiking and unmatched dining. Our property features an open floor plan main floor with a kitchen, dining and living area that neighbors the master bedroom and bath. The back deck is a accented with string lights, a grill and comfortable outdoor furniture. Down stairs has two guest rooms with queens beds, a full bathroom and a den with full futon and tv.

Guest favourite
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.
Cabin in Winhall
4.91 out of 5 average rating, 161 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, 306 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!

Top guest favourite
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 homes in Dover
5 out of 5 average rating, 210 reviews

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.

Top guest favourite
Cabin in Winhall
4.96 out of 5 average rating, 369 reviews

Dog Friendly A-Frame Retreat near Hiking, Skiing

Escape to The Vermont A-Frame, our dog-friendly retreat on the edge of Green Mountain National Forest! This cozy 2-bedroom cabin comfortably sleeps 4 and features a stone fireplace, fast WiFi for remote work, and a fire pit. Perfect for a nature retreat, whether you're here to ski, hike, or simply relax, it's your ideal home base for exploring Southern Vermont. Find us on social media! @thevermontaframe

Top guest favourite
Home in Jamaica
4.93 out of 5 average rating, 123 reviews

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

When is the best time to visit Winhall?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$697 CAD$707 CAD$549 CAD$351 CAD$322 CAD$348 CAD$419 CAD$425 CAD$377 CAD$425 CAD$396 CAD$658 CAD
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Quick stats about vacation rentals that are pet-friendly in Winhall

  • Total vacation rentals

    Explore 100 vacation rentals in Winhall

  • Nightly prices starting at

    Winhall vacation rentals start at $206 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,820 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space and kid-friendly amenities

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    100 of Winhall vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winhall rentals

  • 4.9 Average rating

    Winhall stays are highly rated by guests—averaging 4.9 out of 5!

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