Holiday rentals in West Windsor

Cozy - Killington 40 min. Woodstock-Hanover-Piano!

Luxurious, well appointed cottage - Beautiful sunrise view located between Woodstock VT and Hanover NH. Inspiring treat for musician’s getaway is a fully restored 1929 Steinway Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer. VERY comfortable queen bed. Romantic getaway in the woods, relax, work in peace, explore the beauty and history of the area. Hiking, biking, fishing, hot air balloon rides and shopping are all close by. Long (90 day) or weekend rental

Custom cabin on Mt Ascutney, sweeping Hill Views

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.

Designer Cabin Firepit Trails Near Woodstock, GMHA

Ascutney Lofts offers modern, serene retreats nestled in the heart of Vermont’s natural beauty. Thoughtfully designed with Scandinavian-inspired comfort, each space blends style with calm simplicity and offers peaceful privacy and easy access to outdoor adventure, small-town charm, and year-round recreation. Pets, including emotional support animals, MUST be added to your reservation (pet fee applies). Service animals are exempt from fees; supporting documents are required at time of booking.

Chuck's Place

Summer is in full gear! Chuck's is a neat and tidy stand alone home warmly dedicated to your vacation pleasure. Fully stocked! Private and convenient on 7 sunny acres overlooking Mt Ascutney. It's great for folks coming in for hiking, biking-- or absolute relaxation. Brownsville Butcher and Pantry supports many endurance and music events in the village at the base of Mt Ascutney. It's a special gathering place to enjoy wine, beer, ice cream --and the best meat and fish anywhere. We promise.

Red Barn Cabin Near Biking Trails, Woodstock, GMHA

At Ascutney Lofts, our modern cabin is anything but ordinary. Easy access to world-class skiing, pristine hiking and biking trails, and a short stroll to Brownsville Butcher & Pantry. A quick 20-minute drive to the Upper Valley places you close to the area’s best dining, and attractions. Pets (25 lbs limit), including emotional support animals, MUST be added to your reservation (pet fee applies). Service animals are exempt from fees; supporting documents are required at time of booking.

Cozy Mountain Cabin w/ Hot Tub & Incredible View

Plan your summer escape to this contemporary-outfitted cabin w/ an unparalleled view! 5 mins to Ascutney mountain - an outdoor enthusiast’s dream w/ 45+ miles of mountain biking, hiking & running trails. Dine on the 1,300 sq ft deck while taking in the majesty of the mountain. Relax in the hot tub, roast marshmallows in the fire pit or star-gaze w/ our binocular telescope at night. 25 mins to Woodstock! 45 mins to Killington! Your Vermont getaway awaits… *1 dog max for $200/stay

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". A lofted space on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony. For more go to @theloft.vt

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

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.

Meadow View. 35 acres outside your door!

Meadow View - pet friendly home away from home. 35 acres- including 2 trout ponds and 25 acres of wooded trails (perfect for hiking, cross country skiing/snow shoeing!). Featuring a newly remodeled kitchen and bathroom. Minutes from Mt. Ascutney (trails galore, rope tow in the winter). The unit is perfect spot for couples craving time in rural Vermont or for families/outdoor enthusiasts who want to go mountain biking, skiing, hiking. (Okemo 30 min Killington 45 min)

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board

Escape in a beautiful light-filled upscale cabin deep in the woods at Sugar Maple Mountain Retreat. Relax at the end of the day in our hot tub which is shared between our 3 cabins. Steps away from two picturesque lakes, enjoy complimentary seasonal use of our kayaks, paddle boards and snow shoes. Go fishing, biking, hike country roads or trails on the 1275 acres of surrounding preserved land. In winter hop on the VAST trail nearby. 4 WD Required Dec 1- April 15th