Pet-friendly vacation rentals in Winhall

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Winhall

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Guest favorite

A winter scene depicts a cozy log cabin surrounded by snow-covered trees. The wooden structure features a sloped roof and large windows. A path leads to the front porch, which is adorned with holiday wreaths, inviting guests to enjoy the serene winter landscape.

Cabin in Danby

4.89 out of 5 average rating, 296 reviews

April/May special So Vt Cabin Mt Tabor Treasure

April-May18th book 2 get a 3rd free. Local to Appalachian /Long Trail, Little Rock Pond and Homer Stone Trails. Spring Summer: We are a 12 month vacation rental back to back with the National Forest. Great hikes on the AP/LT, swimming holes, 10 minutes to VSF, Minutes to the Manchester. Great place to relax, fire pit with wood. Winter: 35 minutes to Okemo,Stratton Pico, 40 min to Killington and 20 min to Bromley. All pets must be pre-approved Pet fee 45.00 please include your pet fee .

Guest favorite

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

4.88 out of 5 average rating, 197 reviews

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)

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Home in Readsboro

4.86 out of 5 average rating, 125 reviews

Beautiful Vermont! (Pet Friendly)

Our home is nestled in the Green mtns, with quick access to the road. A babbling brook lulls you from the master bedroom, a clawfoot soaking tub, stocked house(this is our home we Airbnb when we're away working ).Hiking, antiques, shops, lakes, ski, snowboard, covered bridges, local inns, mountain views! Scenic roads, nearby Mt. Snow, VAST snowmobile trails, Mt.Greylock, Mass MOCA museum, N.Adams, MA, Berkshires. Bennington Wilmington. Great location! PEACEFUL & PERFECT Vermont getaway! ☺

Guest favorite

A cozy bungalow porch features a welcoming entry door framed by two windows. A dog lies comfortably on the wooden deck, which is partially covered by a pale blanket. The porch is accentuated by a circular chair and a sign identifying the property.

Cabin in Wells

4.94 out of 5 average rating, 192 reviews

Gatsby's Getaway

Ready to disconnect and recharge? Welcome to Gatsby's Getaway! Watch the sun rise over the Green Mountains and Little Lake from the comfort of your deck. If the weather disagrees, enjoy your coffee in front of the cozy fireplace in your charming bungalow, complete with cathedral ceilings and sliding glass doors. Close to hiking & biking trails, and many outdoor activities. 10 minutes to nearby Granville, NY or Poultney, VT. While not technically a 'tiny' house, it is a cozy cabin of 550sqft.

Guest favorite

The tiny house features a modern wooden exterior with large glass doors and a front porch area. A small set of steps leads to the entrance, while outdoor seating is situated nearby. Lush greenery surrounds the home, providing a natural setting.

Tiny home in Clarendon

4.9 out of 5 average rating, 226 reviews

Secluded tiny house resort - DOG FRIENDLY

New tiny house, never lived in, but made to be comfortable. All amenities included: Air-condition, heat, WiFi, TV with cable, shower, tub, dry toilet, small full loft bed and full size couch futon, fire pit, river for swimming or fishing right out the door, small refrigerator, microwave, hot plate, toaster.ear three ski resorts (Killington, Okemo, Pico), Appalachian Long Trail two miles away, swinging bridge on trail beginning, White Rock hiking, lakes near for paddle boarding. Hot tub shared.

Guest favorite

The exterior of a newly renovated white house is presented, featuring a prominent front entryway with steps leading to a porch. Large windows allow for ample natural light. A grassy yard surrounds the home, with a dog resting peacefully on the ground nearby.

Home in Mount Holly

4.92 out of 5 average rating, 118 reviews

Modern Farmhouse - 2 kings, minutes to Okemo!

Newly renovated property surrounded by picturesque mountains with views from every bedroom. Relax in our cozy 4 bedroom, 2 bath home, large enough for your whole family to come together. Sleeps 11. Dog friendly. Arcade games and firepit. Large yard. Excellent place to work remotely. Enjoy hiking, fishing, biking, kayaking, skiing & golf nearby. Explore nearby Ludlow, Woodstock, Manchester and Weston. Okemo & Jackson Gore resorts are less than 10 minutes away. Killington Mtn 30 min drive.

Guest favorite

A cozy bedroom is presented with a spacious bed adorned with a white quilt and decorative pillows. A large window offers a serene view of Sadawga Lake, complemented by a window seat nearby. Light wooden cabinetry and overhead lights add warmth to the setting.

Tiny home in Whitingham

4.91 out of 5 average rating, 99 reviews

Cozy Lakeside Tiny Home, Near Skiing

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store, located 5 minutes away, will make you fresh egg sandwiches, pastries, and coffee. For lunch, come in and get fresh made subs or our famous brick oven pizza slices. A perfect getaway for couples, friends, or family in every season. Enjoy kayaking, fishing, ice skating and boating on serene Sadawga Lake. It's a quick drive to skiing at Mount Snow, shopping and dining in Wilmington, and direct access to the VAST trail.

Guest favorite

The living area features a cozy sofa adorned with decorative pillows, positioned around a central coffee table. Natural light enters through a large window beside the door, illuminating the wood-paneled walls and rustic floor. A simple area rug adds texture to the space.

Cottage in Hartland

4.93 out of 5 average rating, 116 reviews

Adorable Dog Friendly Cottage w/FIOS

Bright and clean 2-story cottage on a shared 20-acre sanctuary. With a view of the hills, flanked by woods and open pastures, the cottage includes 2 bedrooms (1 up w/Queen, 1 down w/full bed, 1 bathroom (2nd floor - shower only), kitchen/living/dining area (2nd floor), and laundry. 10% off for guests using only one bedroom (cannot be combined with other discounts). See details in property description. Dog sitting & walks sometimes available - please inquire for rates & info ahead of time.

Guest favorite

An outdoor seating area features a glass-top table surrounded by six metal chairs, with a vibrant umbrella providing shade. A relaxed seating option is available on a nearby lounge chair. A grassy area and additional structures are visible in the background.

Home in Manchester

4.85 out of 5 average rating, 228 reviews

Keys to Vermont

We have the keys to a great vacation in Southern Vermont, located in a quiet family neighborhood within walking distance to Manchester designer outlets. “Mom’s Place” is a three bedroom two bath ranch, just minutes from several major ski resorts, beautiful hiking trails , parks and recreation areas. Two minutes from some great restaurants and bars. The house has a fully equipped kitchen, laundry , Wi-Fi and is dog friendly. Come enjoy all Vermont has to offer in the comfort of Mom's home.

Guest favorite

Tiny home in Jamaica

4.94 out of 5 average rating, 1,256 reviews

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Top guest favorite

Chalet in Dover

4.98 out of 5 average rating, 109 reviews

Mountain Chalet: Private Brook - Hot Tub - Firepit

The Brook House Vermont is set back in the trees and unbelievably cozy. It's a place to reconnect while listening to the brook. To enjoy big meals, conversations, and games by the fireplace. To bask in the sun or do yoga on the deck, or gaze into dark, starry skies from the hot tub and fire pit at night. There's skiing mins away at Mount Snow, swimming at Harriman Reservoir, as well as hiking, golf, mountain biking, antiquing, breweries, and some of the best cuisine VT has to offer.

Guest favorite

The exterior of the home displays a warm wooden facade complemented by a metal roof. Surrounded by snow-covered ground and trees, the structure features large windows and a balcony on the second floor, inviting natural light and outdoor views.

Home in Peru

4.91 out of 5 average rating, 162 reviews

Beautiful Bromley/Manchester VT Retreat w/hot tub

Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester, Beautifully remodeled VT vacation getaway nestled in the Green Mountains. Closest skiing to quaint Manchester VT, minutes from snowmobiling, hiking, fine dining and shopping. This home features 5 bedrooms, 3 with queen beds including 2 Masters, and 2 bedrooms with double bunks. Comfortably accommodates 12 people. Perfect for 2 or 3 families to enjoy any season in Southern Vermont's beautiful Green Mountains!