Holiday houses in West Windsor

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.

Chuck's Place

First snow! Winter is upon us! Chuck's is a neat and tidy stand alone home warmly dedicated to you and your vacation R&R. Fully stocked! Private and convenient on 7 sunny acres overlooking Mt Ascutney. Ascutney Outdoors is in it's 10th year with affordable family skiing -- come ski & skin with the locals! Then head to Brownville Butcher and Pantry, an active gathering place in the village. Excellent beer and wines. Best meats and fish anywhere! Or head back home stoke up the fire and relax!

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.

Midcentury Hillside Retreat - Summer Paradise

Enjoy this peaceful retreat in the heart of the Green Mtns and surrounded by 130+ acres of private woodland. Dramatic field stone fireplace and spectacular panoramic views of Mt Ascutney into New Hampshire from the entire living space. Large chef's kitchen. Private master suite and two guest bedrooms. The perfect get-away for relaxing with family and friends. Exceptional hiking, biking and Connecticut River adventures. Near GMHA and Woodstock. Great restaurants, fun village shopping nearby.

Mountain Edge Living

Enjoy life in the mountains with outdoor adventures abound. Bike Hike Ski 3BR Sleeps 6 Trailside Slopeside Townhouse in Brownsville/West Windsor Vermont next to Ascutney Outdoors and Ascutney Trails. Walk into the spacious ground-floor entry and store your gear. Master Bedroom, Kitchen, Dining Area, Family Room, Hall Bath, and Laundry ALL on the entrance/ground level for an easy move-in experience. Step down to the lower level to the game room, another full bath, and 2 spacious bedrooms.

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.

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.

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.

The Berghüttli: Glowing Swiss Hut in the Forest

The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.

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)

7-Acre VT Estate | Barn, Trails & Mountain Views

Peaceful 3BR home Near Woodstock & Mt. Ascutney Step onto seven private acres where mountain views stretch to the horizon and the only sounds are birdsong and the rustle of leaves. This modern country home is the rare Vermont retreat that has it all - room to roam, horses welcome, and enough comfort inside to make you forget about unplugging was ever hard. Whether you're here to ride, hike, explore Woodstock's villages, or simply do nothing, this is your base.