Hotel holiday rentals in Windsor County

Historic Hubble Shire Farm Inn--French Queen

An historic federal meets modern design with this impeccably resurrected home from 1832 situated just steps from the village greens of Chelsea, a quintessential Vermont town. All modern electrical, plumbing, bathrooms with all the historical charm of the 1830s. The French Queen features a queen hand carved bed, 19th century French commode and nightstands, elegant porcelains, a lounge chair and decorative fireplace and large private bath across the hall. A gourmet breakfast is included.

A Bunk at Wise Pines

Wise Pines is a Holistic & Sustainable Inn/Hostel that offers a unique farm experience. In the rural woods of Vermont, The All Trails Bunkroom can accommodate 8 people and may hold up to 12 people total in this two level renovated barn. There is a small seating area and a large upper deck that over looks the property. On 40 acres of land, complete with walking trails and a pond to sit by. The owners live on property with their dogs, ducks & chickens. All bunks are first come first serve.

Historic Stagecoach Stop Hostel room #1-1 single

The Stagecoach Stop Hostel, located on the second floor of the historic (ca.1830) Church-Orr House, offers accommodations for up to six people in three refurbished bedrooms. The Church-Orr House was once a stagecoach stop on a Boston to Montreal stage run and once again offers lodging for travelers. It’s very handy place to stay if you are visiting Vershire, and a good alternative to a motel for people visiting adjoining towns such as Chelsea, West Fairlee, Thetford, or Fairlee.

Sleep Woodstock - 2 Double Beds - Dog Friendly!

You come to Sleep Woodstock Motel to explore, to hike, to fish, to ski, to shop, to attend events, antique, enjoy nature - to escape and have fun! When you're ready for a good nights sleep after a busy day, our updated rooms are just the place to lay your head! Our rooms are cozy and unexpected, and feature our signature “Wall of Art” unique to each room. Located 4 miles to Woodstock, 12 miles to Quechee Gorge, 8 miles to Saskedena Six, and 10 miles to Killington Ski Resort.

Killington Grand Suite Ski On/Off Kitchen Sleeps 6

Large hotel suite, sleeps 6, with full kitchen at the Killington Grand. full service resort with spa, gym, outdoor heated pool, bar, restaurant, hot tubs, sauna, steam, snow shoe, hike, bike or shop at the outlets in Manchester VT! Ski in/Ski out, with ski check, valet parking, outdoor heated pool and hot tub with mountain view, on site spa, fire pit, onsite highly rated Prestons restaurant, tubing park, golf course, summer activity center, game room, onsite store

Private Suite in Historic Inn

Enjoy a private room, bathroom & shower in the historic Chester Inn, circa 1780. This charming property is conveniently located on Main Street in walking distance to restaurants, shops & galleries (please see guidebook for recommendations!). Public hiking /snowshoeing trails can be entered right through the backyard & Okemo mountain is just a short drive away! Although the building is bed & breakfast style we do not provide breakfast.

Swiss Farm Inn - RM9 "Solitude" 1 Queen Bed

Rent a room at the Swiss Farm Inn in Pittsfield, Vermont! Nestled between Killington and Sugarbush, this charming old farmhouse turned inn is ready to welcome you. Each room features a private bath, and you'll have access to common areas like the living room, dining room, and more. Just minutes from Killington and Pico ski resorts, this is the perfect getaway! Note!!!  Your stay includes fantastic breakfast options (Free!!!).

Killington Resort to 4 minute drive

Welcome to Killington Mountain Resort Tapestry Our mountain lodge is located on the 6th hole of Killington Golf Course, less than two miles from Killington Ski Area. In addition to the slopes, hike and bike trails for all skill levels can be found nearby, as well as plenty of local restaurants within a mile of us. After a busy day, dine in front of our cozy fireplace or soothe your muscles in our 20-person hot tub.

Premium 2 Queen Beds Greenbrier Inn Killington, VT

Located in the heart of Killington. We are modern hotel with Vermont country charm. Family owned and operated. All air-conditioned Guest Rooms, with close access to skiing and golf. Guests from around the world have experienced the warmth and casual elegance of the Greenbrier Inn and Gift Shop. Stay, Shop, and Ski in the beauty of Vermont's Green Mountains.