Hotels in Windsor County

Pamper Yourself at Jackson Gore

This plush two room suite is steps from skiing, riding, snow-tubing, and more. Pull your car into our covered Parking Garage and enjoy your vacation. -Room one contains two queen beds, a sitting area with TV and bathroom with walk-in shower. Room two has a full kitchen with pots, pans, utensils, plates, drinking glasses, and silverware, living room with queen fold out sofa, fireplace and TV, dining area and a desk for working or studying remotely. Room two also has a full bath and washer?dryer.

Lace Room #3: Birch Ridge Queen Suite. Hot Tub/Bus

Discount Lift Tickets & Rentals Available Welcome to the Lace Room at Birch Ridge Killington! This ground floor haven offers a queen bed & sofa for 2 guests. Relax w/ smart TV & upgraded ensuite bath feat. a luxe tile shower. As our guest, enjoy shared amenities. The lounge has a gas fireplace, coffee station, TV & board games. Dine in the dining room or have fun w/ pool table & shuffleboard. Don't miss 2 shared hot tubs w/ mountain views. Book now! (Option to book entire property/add'l rooms.)

Quaint Queen Room & Private Bath

Enjoy a private room & bathroom with tub in the historic Chester Inn, circa 1780. This charming property is conveniently located on Main St 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! EV charging is close by (in the public lot on Cobleigh St) Although the building is bed & breakfast style we do not provide breakfast.

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.

Clear River Inn - 2 Double Beds (2nd Floor)

Centrally located on scenic Route 100, the Clear River Inn is the ideal destination for every season. Skiing, snowmobiling, leaf peeping, river tubing, hiking, mountain biking & disc golf are just a few of the various activities all within a 10 mile radius of the property. Home to the Clear River Tavern - VT's true hidden gem, just walking distance from your room. (Closed Mondays & Tuesdays)** **PLEASE NOTE - THE TAVERN WILL BE CLOSED FOR THE SPRING & WILL REOPEN ON MAY 31ST!**

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

Near Killington Ski Area | Hot Tub. Mountain Views

Stay surrounded by mountain views at Killington Mountain Lodge, part of the Tapestry Collection by Hilton. Nestled beside the 6th hole of Killington Golf Course and less than 2 miles from Killington Ski Area, this lodge-style escape puts outdoor adventures, après-ski vibes, and cozy comforts all at your doorstep. Enjoy a 20-person hot tub, on-site bar, and continental breakfast before hitting the slopes, trails, or downtown Killington restaurants, just minutes away.

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! So when you're ready for a good nights sleep after a busy day, our updated cozy rooms are just the place to lay your head! Experience a sustainable stay at Sleep Woodstock, our solar-powered hotel located 4 miles to Woodstock, 12 miles to Quechee Gorge, 8 miles to Saskedena Six, and 10 miles to Killington Ski Resort.

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 farmhouse-turned-inn is ready to welcome you. Each room features a private bath, and guests enjoy access to shared spaces such as the living room, dining room, and more. Located just minutes from the Killington and Pico ski resorts, it’s the perfect mountain getaway! Note: Your stay includes fantastic breakfast options — free of charge!

Ferndean Place

Nestled in 300 acres of private land on a dead end road, you will find Ferndean conveniently located five miles from Woodstock and Quechee. This private road is somehow still a secret and offers woodland hiking as well as access to the Appalachian trail. If you want to be immersed in nature, this is your spot. And yet the duplex offers all the amenities of comfort. High speed internet and modern appliances; this is an easy living retreat.

Steps to Ottauquechee River + Breakfast & Kitchen

Wake up to river views, grab a pastry by the fire, and plan your day around covered bridges, farm stands, and backroad adventures. On the River Inn feels more like staying at a stylish friend’s countryside retreat—there’s a pool, sauna, cozy lounge, game room, and fireplaces everywhere. Whether you’re here to hike, ski, leaf-peep, or just curl up with a book and cider, this Woodstock spot makes it easy to slow down and feel at home.

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.