Hotels in Windsor County

5 out of 5 average rating, 3 reviews

American Classic Room #7: Birch Ridge King Suite

Discount Lift Tickets & Rentals Available! Welcome to The American Classic Room at Birch Ridge Killington! Ideal for comfy stays, the room features a king bed w/ luxe linens for restful sleep, smart TV, gas FP & 2 chairs for relaxation. A/C & mini fridge add to your comfort. Ensuite bath includes a combo tub/shower & plush towels. Enjoy shared amenities like a lounge w/ gas FP, coffee station & bar. Dine or socialize in separate dining rm. Pool table, shuffleboard & outdoor hot tubs. Book now!

4.93 out of 5 average rating, 30 reviews

A cozy room is presented with a queen bed covered in a light quilt. Natural light filters in through two windows, flanked by neutral curtains. Two bedside tables with lamps are positioned beside the bed, and a small chair is placed against the wall.

Hotel room in Chester

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.

4.84 out of 5 average rating, 38 reviews

The bunkroom features four wooden bunk beds, providing a total of eight sleeping spots, arranged in two rows. A ceiling fan is present for air circulation, and natural light enters through a large window, brightening the space with a soft glow.

Shared room in Woodstock

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.

4.88 out of 5 average rating, 118 reviews

A snow-laden scene features a prominent sign for the Clear River Inn, displaying the name and directions to the tavern. Flurries fall gently in the air, while the inn's building and rooftops are dusted with snow in the background.

Hotel room in Pittsfield

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!**

An outdoor heated pool is visible, illuminated warmly against a backdrop of snow. The multi-story hotel structure showcases a series of balconies overlooking the pool area, with guests enjoying the water. Twilight creates a serene atmosphere around the resort.

5 out of 5 average rating, 5 reviews

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

4.58 out of 5 average rating, 74 reviews

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.

4.94 out of 5 average rating, 98 reviews

A cozy room features two double beds, each dressed in crisp white linens. Wall art showcases a variety of styles above the beds, while bedside lamps provide soft illumination. A small table is positioned between the beds, enhancing the room's functionality.

Hotel room in Woodstock

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.

5 out of 5 average rating, 7 reviews

A serene guest room is furnished with a spacious bed, a soft couch, and a wooden dresser. Natural light filters through sheer curtains, enhancing the warm wooden accents. Decorative wall art and a small lamp on a side table add character to the inviting space.

Hotel room in Pittsfield

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!

Casa particular in Woodstock

A spacious dining area features a long wooden table surrounded by several chairs, with natural light streaming through large windows. The room is adorned with wooden beams and a stone fireplace, creating a warm atmosphere complemented by soft seating arrangements and decor.

4.83 out of 5 average rating, 6 reviews

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.

4.67 out of 5 average rating, 3 reviews

The exterior view of On the River Inn is presented, showcasing a well-maintained property surrounded by greenery. A prominent wooden sign is visible at the entrance, complemented by an American flag. The backdrop features a distant tree line and clear blue skies.

Hotel room in Woodstock

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.

5 out of 5 average rating, 7 reviews

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.