Windsor Vacations

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Your Windsor Vacation

Food, history, entertainment and more … There's so much to experience with a Windsor vacation package. And with the ability to customize your city break, you know it'll be one that's hard to forget. If sightseeing is on the agenda during your trip to Windsor, stop by leading attractions like Mount Ascutney, Blow-Me-Down Bridge and Mt Ascutney State Park. Whoever you're escaping with and whether your budget is big or small, your ultimate Windsor vacation is only clicks away with Expedia.

Discover the most popular places to visit in Windsor

American Precision Museum

You can spend time exploring the galleries in American Precision Museum in Windsor. Wander the riverfront in this quaint area.

American Precision Museum

Path of Life Garden

Explore the great outdoors at Path of Life Garden, a lovely green space in Windsor. Wander the riverfront in this quaint area.

Path of Life Garden

Brownsville Trail

You can take time to visit Brownsville Trail during your travels to Windsor. Discover the mountain views in this family-friendly area, or seek out the ski slopes.

Brownsville Trail

Windsor Hotel Deals

Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins

3 out of 5
122 Best Rd, Windsor, VT
$190 nightly
The price is $208 total per night from Nov 9 to Nov 10
$208 total
Nov 9 - Nov 10
Total with taxes and fees
9.6/10 Exceptional! (11 reviews)
"An absolutely stunning property! The cabin was clean, well stocked and perfectly located to see the gorgeous sunrise. So very grateful for our quick trip at Fat Sheep Farm. Looking forward to returning!"

Reviewed on May 6, 2025

Fat Sheep Farm & Cabins
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

2.5 out of 5
25 Airport Road, West Lebanon, NH
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $164 total per night from Oct 30 to Oct 31
$164 total
Oct 30 - Oct 31
Total with taxes and fees
8.2/10 Very Good! (1,037 reviews)
Great place to stay close to Woodstock, VT
"Rooms were clean. Buffet breakfast included. Pool and hot tub were nice in a huge covered area. Convenvient location. Would stay again."

Reviewed on Oct 19, 2025

Fireside Inn & Suites West Lebanon
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$389 nightly
The price is $428 total per night from Nov 16 to Nov 17
$428 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (538 reviews)
"It's a lovely property and the staff are very nice. They seemed a but overwhelmed (or short staffed). Our room wasn't serviced because they didn't arrive until very late in the day each day. By that time, we were in the room preparing for the evening. We just traded out our towels for fresh ones ..."

Reviewed on Oct 13, 2025

Woodstock Inn & Resort
See all 2,571 properties in Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Population
2,100
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Mt Ascutney State Park, Harpoon Brewery and Quechee State Park

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Frequently asked questions

How much does a Windsor vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. But how much your vacation to Windsor costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Windsor?
April, May and October are great times to look for cheap Windsor vacation packages. Opting to travel in quieter months means you'll typically find reduced prices on hotels and flights.
How many days is enough for Windsor?
Generally, a handful of days is enough to visit the main attractions during your Windsor vacation. But if you'd like to have more time to relax or take day tours, think about extending your trip.
Is it worth booking a vacation package to Windsor?
Windsor is a good vacation destination with attractions like American Precision Museum among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Windsor vacation promises a good time for everyone.
How to find the best Windsor package deals?
Landing a cheap Windsor package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Windsor package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Windsor vacation as a package?
You can enjoy significant savings on your next Windsor break by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Windsor?
Secure fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Windsor vacation.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
If you're anything like us, you love going away but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Windsor trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.