House vacation rentals in Stockbridge

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.

Cozy Contemporary Downtown Texaco

Stay with us if you’d like to be in the center of downtown Castleton. Stores, restaurants, the college and hike/bike rail trail are an easy walk. This is a very convenient location. We are also a short 30-40 minute drive to Pico and Killington ski areas. Five minutes to Lake Bomoseen. Recently updated, heat and AC, full bath, Wi-Fi, Qled tv, a comfortable king sized memory foam bed, a complete kitchenette. Reserved parking adjacent to entry. Everything you need for an overnight or longer stay

Escape to Vermont

Welcome to the Red House at Stony Brook! This remodeled 1800's farmhouse offers peace, solitude and comfort in Vermont's national forest. Gaze at stars from the bedroom window and decompress in the mountains. Or, set out for a day of cycling, hiking, skiing and exploring all Vermont has to offer. A chance to experience wildlife, such as moose, birds, bears, turkeys and more. Nearby are Killington Mtn, Sugarbush, famous cycling roads, and several of VTs world renowned eateries and breweries.

Mountain Home ready for you!

Get away from it all in a secluded home atop a mountain in the National Forest. Home with deck and panoramic view of the Green Mountains. Idyllic in all seasons. Summer is lusciously green; fall colors seen from our deck; the magic of winter. Tons of privacy, but minutes from town. 35 min to Killington or Sugarbush; snowshoe outside your door, and x-country nearby. Snow tires or chains needed from Dec.-March. Please note that we cannot help you if your car gets stuck en route to the house.

Birdie's Nest Guesthouse

Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

Cottage in the Heart of the Green Mountains

Welcome to quintessential Vermont! Come stay at my cozy yet spacious, rustic yet modern, much-beloved Red Acre Cottage. Red Acre Cottage is nestled on a scenic ridge in the idyllic town of Rochester, just east of the Green Mountains and right off of Vermont Scenic Byway Route 100, one of the state's prettiest roads. Red Acre Cottage is an easy drive to Killington/Pico, Sugarbush, Mad River Glen, Rikert Nordic Center/Blueberry Hill XC skiing, Suicide Six, and Stowe Mountain.

Affordable, private, surrounded by flower gardens

Enjoy the summer in beautiful Vermont. The guest area is the entire main floor of a large house with my quiet second home above. Private entrance, 2 bedrooms, full bathroom with washer and dryer, speedy fiber optic internet. The open kitchen has full sized stove and fridge with good cookware and appliances, adjacent to a large open living area. On a paved scenic road. Go up to Silver Lake for a swim, head out on any of the back roads for a run or a ride.

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!

Ski home to Trail Creek!

Enjoy Killington at competitive pricing without sacrificing comfort! Located in Trail Creek Condo Association. • Ski, hike, bike, or golf just steps away • Cozy up by the wood fireplace (free wood) • Pool, hot tubs, sauna, and game room at community center • 6-minute walk to Snowshed or shuttle (winter weekends/holidays) • Ski home trail (snow-dependent) • Minutes to restaurants, bars, and shops • Convenient bus stop Adventure and relaxation await!

A million-dollar view near Killington on 60 acres.

This secluded 200 + year old mountain farmhouse is located in the small town of Pittsfield, VT just 5 minutes away from one of the most scenic drives in New England, Route 100. Surrounded by national forest with stunning views of the Green Mountains, this is the perfect place to get away with family or even by yourself. Plenty of room outside on the 60+ acre property with fields and a small pond. In the center of Vermont, it's the perfect home base.

Dramatic Views at the Above the Clouds Guesthouse

As featured in Conde Nast Traveler (1/21/22) Peaceful & impeccable retreat with a 180 degree view of Vermont's tallest mountains. Near Vermont's premier skiing, hiking, & outdoor adventures, you’ll love the sunset views and cozy atmosphere (huge sheepskin in front of the fireplace) and the attention to detail (live-edge wood details, spa-like bathroom). This is an incredible retreat for couples and families, adventurers and business travelers alike!

Forest Hideaway

Our single story 2 bedroom 1 bath home is located within 30 minutes of Mad River Glen and Sugarbush ski areas and the quaint towns of Bristol, Richmond and Waitsfield. Drive another 15 minutes to Burlington or the Bolton Valley Ski Area. Hiking, biking and cross country skiing trails nearby, or just sit on the porch and enjoy the sounds of the nearby river. Snow tires and front wheel or 4 wheel drive vehicles necessary during the winter months.