Hotels in Windsor County

4.85 out of 5 average rating, 27 reviews

A well-equipped kitchen features wooden cabinetry, stainless steel appliances, and a countertop. A dining table with four chairs is positioned nearby. In the living area, a sofa and armchair provide comfortable seating, with soft lighting from a floor lamp illuminating the room.

Hotel room in Ludlow

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.

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Hotel room in Hartford

4.67 out of 5 average rating, 3 reviews

4 ski resorts nearby, including Killington(!)

Whether you're here on business or leisure, the White River Inn & Suites, conveniently situated close to both I-89 and I-91, is the ideal choice when visiting the scenic Upper Valley regions of Vermont and New Hampshire. The Inn is close to Dartmouth College, Dartmouth Hitchcock Medical Center, as well as the Lebanon Municipal Airport. Explore the curiosities and artifacts of the Main Street Museum, shop the charming Power House mall, or take a scenic train ride on the White River Flyer.

ValueSkiingHospitality

5.0 out of 5 average rating, 4 reviews

A view from a ski lift captures the vibrant yellow and red buildings of the Jackson Gore Inn. Snow-covered slopes are visible below, with skiers and snow tubers enjoying the winter landscape. Blue skies and distant mountains create a serene backdrop.

Hotel room in Ludlow

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.

FamilyLocationCleanliness

5.0 out of 5 average rating, 10 reviews

Hotel room in Woodstock

Sleep Woodstock Motel - King: Room #1

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.

ValueLocationCheck-in

4.77 out of 5 average rating, 102 reviews

Hotel room in Chester

Whimsical Room & Private Bathroom in Historic Inn

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 provided across the street! Although the building is bed & breakfast style we do not provide breakfast.

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4.66 out of 5 average rating, 145 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.

LocationFamilyHospitality

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.

5.0 out of 5 average rating, 6 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

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Hotel room in Brownsville

Beautiful mountain retreat villa

Nestled in the quiet community of Brownsville within West Windsor is our charming mountainside retreat. Great hiking nearby along with other activities like Ben and Jerry tours, the Adventure Zone, Billings Farm and Museum and more. The Maple Kitchen is a great onsite restaurant offering local flavors and sourcing. The 970 sq ft 2 bed/2 bath is great for up to six guests with 1 king bed, 1 queen bed and a sleeper sofa.

Sleep qualityViewComfort

4.75 out of 5 average rating, 115 reviews

A large sign for Clear River Inn is positioned prominently on the property, featuring vibrant blue and green colors. The sign displays directional information for the tavern located at the back, along with contact details and a scenic mountain graphic. Surrounding flowers add a touch of nature to the scene.

Hotel room in Pittsfield

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)**

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The exterior of White River Inn & Suites is depicted, showcasing a spacious building design with light-colored siding and a welcoming entrance. Ample parking is visible in front of the property, surrounded by lush greenery and scenic hills in the background under a partly cloudy sky.

Hotel room in Hartford

4.67 out of 5 average rating, 3 reviews

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.

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4.84 out of 5 average rating, 44 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.

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A cozy guest room features two spacious beds adorned with floral-patterned bedspreads. A lamp provides soft lighting beside the beds, while large windows offer views of the outdoors. A small table with chairs is positioned near the window, creating a relaxing spot.