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Newly renovated. Minutes to Slopes & Trails

Healdville Hideaway has 3 acres of rural charm located on the backside of Okemo Mountain. Charm is a plenty in this 1500 SF single story, newly renovated home with views of the mountain & fields full of wildlife. This modern country decorated home provides the perfect comfortable setting for single or multi family enjoyment. The fully functional kitchen is available for making a quick snack or a full meal. The back acreage is perfect for building a snowman or doing a little cross country skiing.

1868 Victorian Farmhouse-20 min Okemo-Magic MTN

Our Historic Victorian is less than a mile to charming Chester Village-enjoy quaint restaurants and pubs, antique shops, art galleries, yoga studio and a country market. Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers, covered bridges + breweries. Close proximity to the best of Vermont's ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington) Come experience why Chester has been voted one of the top 10 most beautiful towns in Vermont!

Stylish Ascutney Cabin •View •Chef’s Kitchen •Pets

Wake up in a luxurious bed in a stylish cabin with panoramic Vermont views and a little reading balcony. When ready, step down to the living area to look at faraway hills through oversize doors, a hot cup in your hands. Make breakfast in your Chefs kitchen. Sit/read/talk. Go for a hike. Or a scenic drive to your pick of Woodstock, Simon Pearce, Harpoon Brewery, Okemo, or Twin Farms. Cap it off with a night gazing at stars around the firepit. The Red House is all this and more....

Beautiful Woodstock Home-Perfect for entertaining

Newly renovated - 4 bedroom, 3 bath house, perfect for relaxing or entertaining. Close to all that the Woodstock Village and the Upper Valley has to offer. Amazing location! Only 1.5 mi to the Woodstock Green. Explore the property and feast on the blackberries in summer, raid the tomato garden in the late summer/early fall, and pick the wild fall apples for munching or baking. Bring your snowshoes or cross country skis (in winter) or hiking shoes in summer and explore the property and beyond!

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

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.

Modern Comfort Meets Country Charm | 3BR Estate

Escape to our serene 3BR Vermont home on 7 acres, 5 min to Mt Ascutney and 15 min to Green Mountain Horse Association. 30 min to Woodstock. Revel in a sun-filled living room, modern family room, fully equipped kitchen, and an elegant dining area. Comfortable bedrooms promise restful nights, and mornings bring views of nature's splendor. Enjoy the patio, gather by the firepit, or stable your horses in our barn. A perfect mix of adventure and tranquillity awaits your family or quiet retreat.

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.

Greystone 1830

"Greystone" is a charming stacked granite home built in the 1830's as a tavern and one of 4 original structures that made up Hammondsville VT. Greystone is just miles from Woodstock, and down the road from the Green Mountain Horse Association (GMHA). It's a short drive to Killington or Okemo and many other Vermont destinations. Greystone is just off VT Rt 106 on a large lot with a circular driveway and plenty of room for parking. The home is fully renovated and modernized.