Pet-friendly vacation rentals in Stockbridge

Stylish Vermont Cabin | Views · Trails · Luxe

Combining sweeping views of distant hills with complete privacy and wraparound porches on two sides, the Red House is a custom cabin built for couples and smaller families. Surrounded by working farms and within easy reach of trailheads to hike or bike Mt Ascutney, or to visit Woodstock, Hanover, Ludlow and the Upper Valley, the Red House sits among some of the best restaurants in Vermont and awaits the discerning traveler who has earned the right to do absolutely nothing and experience it all.

The Birch Perch! Treehouse with spa and fire pit!

Romantic Honeymoon or fun family fantasy come true this treehouse has it all! Built by The DYI Network Treehouse Guys! Every detail custom crafted in this home in the tree tops makes your ultimate Vermont experience. All just 8 minutes to the lifts at Sugarbush. Kitchenette, cast iron stove, clawfoot tub, washer/dryer, AC, & outdoor shower all encased in a whimsical perch near skiing, waterfalls, biking and hiking. Incredible hillside views from your private deck! Romantic Hot tub in the trees!

Genuine Vermont Sugar House on 70 peaceful acres.

Stay in this genuine Vermont sugarhouse. Our family took great pride in making Maple Syrup and now we take that same pride in sharing this private piece of Vermont with you, our guests. There are trails that will take you through our 70-acre property including the sugar bush we used for the sugarhouse. Relax in the quiet beauty of rural Vermont. Located near the geographical center of VT. We do welcome friendly housebroken dogs. Please see other details under show more. Part of Three Maples LLC.

Cozy Bow House Perched in Trees w/ Hot Tub & View

The cozy Bow House is perched up above a lovely valley and boasts large south facing windows, a unique bowed loft and a warm, inviting space to relax. Up a charming dirt road past Brushwood & Fairlee Forests with hiking, biking and ATV trails nearby. Lake Fairlee is a scenic 10 min drive; 15 min to Lake Morey & I-91 and 30 min to Dartmouth College. Enjoy the glow of the rising sun and beautiful views above the fog, unwind in the hot tub surrounded by the magical woods and wildlife of Vermont.

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

The Guest House at Chandlery Farm

This classic Vermont farm estate has everything that description implies: end-of-the-road privacy with breathtaking views, where the only sound is the wind rustling through the leaves. The manicured gardens, stone walls and quaint but luxurious home seem plucked from classic American folklore. Guests can drink their morning coffee while soaking in views of rolling pastures and forested hills, and spend their days exploring the property's trails, and the beautiful towns and countryside nearby.

1958 Classic "Hunting Cabin" w/ Breathtaking Views

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

The Guest House at Sky Hollow

This quiet 120 acre hilltop house on an 1800's farm turned homestead offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

Yurt In The Woods - Come to the Yurt.

The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for Weekends. The month of October I require a two night stay. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available June - October

Killington area home - 4 seasons - hot tub and A/C

Set on a private road in the hills of Pittsfield, our house welcomes you year-round. Right in the heart of the Northeast’s best winter-sports, it's convenient to Killington ski resort, VAST snowmobile trails, Mountain Meadows cross country skiing and Green Mountain National Golf course. Furthermore, there are wonderful hikes and mountain biking to be done on the property and beyond - particularly beautiful in the fall.

Cozy 4-season Cabin on Pond - "East Cabin"

Take refuge in a cozy log cabin with abundant access to Vermont's Green Mountains and rolling foothills. A quick drive to Woodstock and Quechee, the cabin is located on quiet dirt road with beautiful south-facing views overlooking the town of South Royalton, just a mile away. Spring-fed pond is steps from the cabin, take a dip! Follow the trails through the woods and fields and enjoy this pristine piece of Vermont.

Scandinavian design Cabin hiking trail + hot tub

Welcome to our charming cabin nestled in the heart of the woods, where comfort meets tranquility. This 400 sq. ft retreat is bathed in natural light, boasting high-quality appliances, strong WiFi and thoughtfully curated design furniture to ensure a cozy and memorable stay. Relax in our private Goodland wood burning hot tub. Goodland wood burning hot tub is available 365 days a year. EV charger level 2 available.