Hotels in Windsor County

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.

Sleep at Woodstock Motel – King: Room #3

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 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.

King & Queen Bed 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! EV charging is available across the street! Although the building is bed & breakfast style we do not provide breakfast.

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!**

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.

Clear River Inn - 2 Double Beds (Ground 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)**

Skiing & Vermont Nature | Free Breakfast + Kitchen

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.

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.

Under 30 Minutes to Both Killington and Sugarbush

Located in idyllic Rochester VT, centrally located between both Killington and Sugarbush (under 30 minutes to both), ski until your hearts' content in classic Vermont lodging. This is room 1 of 6 in a small inn in Rochester VT, containing a queen bed, and a separate room with a twin bed. There is a full, private bath.