Vacation rentals in Mount Ascutney

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please see: Other Things to

Chuck's Place

With plenty of warm days ahead, we're stoked for the upcoming season. Chuck's a private home on 7 sunny acres overlooking Mt Ascutney. Great for hiking, biking, skiing, snowshoeing- or R&R! A note about Airbnb fees: Airbnb shifted their 15.5% guest fees to the host. We had to raise our rate to compensate. We are loyal to offer accessible ski vacations for your friends & family at the cost of a hotel room! Dollars a day at Ascutney or on your Indy/Ikon/Epic pass. Hit up the 20% on longer stays.

Custom cabin on Mt Ascutney, Fall and Winter Days…

Combining sweeping views of distant hills with privacy and wraparound porches, the Red House is a custom cabin built for couples and smaller families getting away from busy lives. Glorious colors and quiet winter evenings. 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. It awaits the discerning traveler who can do absolutely nothing, yet experience it all!

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.

Modern Cabin | Calm Retreat | Easy Outdoor Access

Welcome to our 2-bedroom, 1-bath modern cabin at Ascutney Lofts, where clean design meets a peaceful Vermont setting. • Backyard with patio furniture, BBQ grill, and fire pit • Open living space with floor-to-ceiling glass and room-darkening shades in bedrooms • Modern kitchen with dining table, dishwasher, and on-site washer/dryer • Mt. Ascutney State Park, Ascutney Outdoors Trails and Brownsville Trail are a short drive away Settle in, unwind, and enjoy an easy stay close to nature.

Entire Cozy Condo for Skiing-Hiking-Biking

Located right on Mt. Ascutney where the Vt100, Vt50 & Overland Races all kick off just outside our front door. Ascutney Outdoors center is right outside, with access to ski trails, snow tubing, cross country and biking trails right at your fingertips. Perfect for beginners and those who want to avoid major crowds. It's a very quiet and cozy space with parking at the front door, a fireplace and fantastic family area. Our place is excellent for couples, solo adventurers and families.

Cozy Mountain Cabin w/ Hot Tub & Incredible View

Plan your autumn 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

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.

Dog-Friendly | Fenced Yard | Fall Hikes & Foliage

Tucked beneath Vermont pines, our cozy A-frame is a peaceful escape for couples, families & furry friends. Soak in the sunlight pouring into the living room, gather in the backyard for s’mores, or curl up by the pellet stove after a day of hiking. It’s a slice of heaven you’ll never want to leave. ✔ Dog-friendly w/ fenced backyard ✔ Queen loft + main-floor bedroom ✔ Full kitchen & fast WiFi ✔ Peaceful deck + outdoor firepit w/ string lights ✔ Grill and table for outdoor dining

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.

Cute, clean and comfy 2 BR studio

Comfortable and private with easy mountainside access. End unit, very quiet, peaceful and cozy. Sitting area with electric fireplace ,TV, stuffed rocking chair and full couch. Little kitchenette with bar sink, mini fridge, coffee maker, and toaster oven. Comes equipped with dishes, glasses, coffee cups and utensils. (NOT A FULL KITCHEN) Bathroom with shower and two separate very spacious bedrooms with queen beds, sitting chairs and one with tv. Comes with free internet.