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.

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.

Cozy Ski-in/out 1 BR Retreat

Come experience mountain living with this cozy ski-in/out guest bedroom at the Jackson Gore Inn on Okemo Mountain. Accommodations for up to 4 guests include 2 queen beds, full bath, TV and free WiFi. Underground heated parking is available on a first come first serve basis. Guests are steps away from skiing, riding, snow-tubing, golfing, biking and hiking. Directly downstairs is a heated outdoor pool, hot tub and sauna. Gather at the fire pit in the courtyard for an enjoyable evening.

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!**

Sleep Woodstock - Dog Friendly King Suite

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.

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.

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!

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.

Close to Quechee Gorge | Indoor Pool. Free Parking

Explore Vermont’s scenic Upper Valley with White River Inn & Suites as your base. Just 1 mile from downtown White River Junction and minutes to Quechee Gorge, Montshire Museum, and VINS, this laid-back property offers spacious rooms, kitchen suites, and a relaxing indoor pool. With free breakfast, parking, and nearby outdoor adventures, it’s a great pick for families and weekend explorers.

1 Bedroom Apt Sleeps 4

1 Bedroom Villa. May also be able to accommodate other dates/guests/room size. Enjoy a stroll around the lake, go for a hike down the Bicentennial Trail or relax on the patio and take in the breathtaking views. Offering a Restaurant, swimming pool, gym area, pool table and a playground amongst many other amenities you’ll surely have something to do for everybody in the family.

Après Inn Newly Renovated Hotel

Newly renovated boutique inn just minutes from skiing, biking, hiking & golf. Walk to Killington’s restaurants, shops & nightlife. Cozy rooms with memory-foam beds, smart gear storage & in-room coffee. Enjoy firepits, yard games, free Wi-Fi, EV charging & easy self check-in. Pet-friendly so your furry friends can join! The perfect basecamp for year-round Vermont adventure.