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Popular places to visit

Windsor Vacations

It's always handy to know a little about your destination before you set off on your escape. Put a mark near Windsor on your map now and start planning for your big adventure!

Windsor is 110 miles (177 kilometers) to the northwest of Boston, a prominent city.

It's an area of Central Vermont- Killington that approximately 2,000 people reside in.

Hotels in Windsor

Traveling to Windsor? Don't wait until the last minute to book one of its 5 available accommodations. Once you've made up your mind, all that’s left is the fun part — actually being there!

The Snapdragon Inn and Kedron Valley Inn are some of Travelocity's top accommodation options in Windsor.

Places to visit in Windsor

Spending time in nature is proven to positively affect both your emotional and physical state of being. Spend time at Mt Ascutney State Park and feel the benefits of connecting with our natural environment. Want more options? Few things give us a peek into bygone days quite like old buildings. Why not take a tour around Old Constitution House and hear a few anecdotes about what went on behind closed doors? But there's more. There is no better teacher than history. Travel back through time for an interesting lesson at Saint-Gaudens National Historic Site.

Where do you fly into for Windsor?

There's nothing more exciting than finally hitting the tarmac in a totally new place. If you're going to Windsor, chances are you'll be disembarking at Lebanon Municipal Airport (LEB). It's about 11 miles (18 kilometers) to the northeast of the downtown area. Pick up your suitcase and get ready to kick-start your adventure!

Frequently asked questions

How much are vacation packages to Windsor?
Starting at just , flight and hotel packages are an excellent way to make your vacation budget stretch further. Watch out Windsor — here you come!
Where can I get the best vacation package deals for Windsor?
Look no further than Travelocity. With 400 air carriers and 665,000 properties worldwide, it’s a breeze to find a Windsor package deal that satisfies your wanderlust.
Why should I book my Windsor vacation bundle with Travelocity?
Travel is all about making fantastic new memories and forgetting all your worries — which is why we have a team of experts available round-the-clock should you need them. On top of that, our Price Match Guarantee ensures you’ll always get the best deal available on our terrific range of getaway packages. So what are you waiting for? There’s no time like the present to secure that vacation you’ve always dreamed of.
Can I save on my Windsor car rental if I book it with my hotel or flight?
Combining your hotel, flight and car into a Windsor vacation package is a great way to score better prices. Plus, having your own car rental gives you total freedom to make your way to all those famous sights you’re hoping to see. Situated 171 kilometersfrom Windsor, Fenway Park is one attraction that should be on your can’t-miss list. Fasten your seat belt and make a day trip of it.
What is the best time of year to go to Windsor?
It all depends on whether you’d prefer to save cash or visit Windsor at its most exciting. The quietest time to explore this part of the world is . But if you’d like to experience this destination at its busiest, consider . Want to save your hard-earned cash? The most affordable month is . typically has the most expensive prices.
Which airport is best for Windsor?
Lebanon, NH (LEB-Lebanon Municipal) is where many tourists touch down. You’ll find it located 18 kilometersnortheast from the heart of Windsor. You can also check out the fares to Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 40 kilometersaway from central Windsor.
What is there to do in Windsor?
Take advantage of the excellent photo-ops at Mt Ascutney State Park, one of the most prominent attractions in Windsor. There’s a lot more to discover in this great destination, so make sure you have enough time to explore some lesser-known sights.
Where should I stay when visiting Windsor?
The Holiday Inn Club Vacations Mount Ascutney Resort is recommended by many visitors. Book now to avoid missing out.
Can I go on vacation to Windsor at this time?
Don’t head to Windsor without the facts about travel restrictions and quarantine policies. Travelocity’s Covid-19 Travel Advisor will fill you in. Our local experts have pulled together all the info you need to make your vacation as hassle-free as possible.