Find luxury hotels in Windsor, VT

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Check availability on Windsor Luxury Hotels

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Dec 7 - Dec 8
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Dec 8 - Dec 9
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Dec 12 - Dec 14
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Dec 19 - Dec 21

Top Windsor Luxury Hotels

Find out more about Windsor

Windsorand its attractions for luxury travelers

In Windsor, Vermont, luxury travelers can immerse themselves in a blend of natural beauty and refined experiences. Start your journey at the picturesque Mt. Ascutney, where hiking trails offer breathtaking views of the fall foliage, perfect for a family adventure or a romantic stroll. Next, explore the charming historic district with its beautifully preserved 19th-century buildings, where you can enjoy boutique shopping and art galleries that showcase local talent. For a unique experience, visit the Simon Pearce Glassblowing Studio, where you can watch skilled artisans create exquisite glass pieces before indulging in a farm-to-table meal at the attached restaurant, set along the serene Ottauquechee River. Families will appreciate the Windsor Historical Society, which offers engaging exhibits about the town's rich heritage, making it a delightful educational outing. The vibrant atmosphere of downtown Windsor, with its selection of upscale hotels, provides an ideal base for your stay. Here, guests can enjoy luxurious amenities, personalized service, and easy access to both outdoor adventures and cultural experiences, ensuring a memorable visit.

Top Windsor Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Great place to stay while skiing at okemo"
Ken 1-night trip
Posted 1 day ago
Pointe at Castle Hill Resort

Frequently asked questions

Are you searching for a great accommodation for your luxury holiday in Windsor?
Expedia can help you arrange a flight to Lebanon, NH (LEB-Lebanon Municipal) airport or Springfield, VT (VSF-Hartness State) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are important when you plan a trip, so we make it easy to find what you'd like to make your stay special. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Windsor offers. Windsor has some interesting things to see and do including American Precision Museum and Harpoon Brewery, so you might want to take in the local sights during your visit.
When can I expect good weather in Windsor?
Planning for the weather is an important factor for making your trip to Windsor a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 62°F, while the coldest months are January and February with an average of 22°F. The snowiest months in Windsor are March, January, November, and February, with each month seeing an average of 15 inches of snowfall.
What's there to see and do in Windsor?
Take in some sights and attractions while you're in Windsor by visiting American Precision Museum, Harpoon Brewery, and Mt Ascutney State Park. If you have spare time during your trip, you might want to make a stop at Connecticut River and Brownsville Trail.
How can I get around Windsor?
It's easier to get around town comfortably when you know your options. If you want to venture outside of the area, hop on a train at Windsor Station.

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