Windsor Vacations from $779
Book a Hotel + Flight or Car together to unlock savings
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.
The Latest Windsor vacation packages
Price found within the past 48 hours. Click for updated prices.
The Shire Woodstock
$1,283
per person
Dec 18 - Dec 21
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8.8/10 Excellent! (997 reviews)
No heater or couldn't find it. Front door needs adjusted in the jamb area, couldn't push it hard enough to get it into a locked position but other than that it was good
Reviewed on Oct 7, 2026
Inn At Mount Snow
$1,441
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
10/10 Exceptional! (127 reviews)
The property was beautifully done, with very inviting public spaces/game rooms and sophisticated decor in the room. The driveway was not obvious from the road and appeared to be a drop-down, so was easily missed. The bathroom was small but well organized. Overall really liked the property.
Reviewed on Oct 5, 2026
Stay near popular Windsor attractions
Brownsville Trail
9.4/10 (3 reviews)
This challenging 5.2-mile trail rewards hikers with panoramic views and the historic Norcross Quarry from the early 1900s. Pack water and wear sturdy boots for the 2,395-foot ascent through Vermont's forests.
Paradise Park
8.8/10 (8 reviews)
Paradise Park offers diverse ecosystems around Lake Runnemede, with well-maintained trails through forests and meadows. Observe abundant wildlife including birds, turtles, and beavers in this peaceful natural sanctuary.
Harpoon Brewery
9.4/10 (23 reviews)
This working brewery offers a unique tasting experience with fresh craft beers and handmade pretzels. Enjoy the communal atmosphere in the taproom overlooking brewing operations or relax in the outdoor beer garden.
American Precision Museum
10.0/10 (2 reviews)
Housed in the historic 1846 Robbins & Lawrence Armory, this museum showcases America's largest collection of significant machine tools. Interactive exhibits highlight how precision manufacturing shaped our industrial heritage.
Ascutney Park
Vermont's first state park offers 12+ miles of trails through former quarries and historic homesteads. Drive the 3.7-mile auto road for panoramic views of the Connecticut River Valley without the summit hike.
Weathersfield Proctor Library
This community-centered library offers a welcoming hub for book lovers and local engagement. Browse their diverse collection or join one of their regular educational programs in this Ascutney gathering place.
Windsor Public Library
This historic library has served as Windsor's community hub since 1882, offering diverse collections for all ages. Browse books, use free Wi-Fi, or join one of their engaging programs.
Silo Distillery
You can take time to visit Silo Distillery during your travels to Windsor. Wander the forest or discover the area's mountain views.
Windsor Hotel Deals
Fat Sheep Farm & Cabins
122 Best Rd Windsor VT
$184 nightly
$201 total
Nov 8 - Nov 9
Total with taxes and fees
9.8/10 Exceptional! (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views!"
Reviewed on Jan 5, 2026
Fireside Inn & Suites West Lebanon
25 Airport Road West Lebanon NH
Fully refundableReserve now, pay when you stay
$128 nightly
$139 total
Nov 9 - Nov 10
Total with taxes and fees
8.4/10 Very Good! (1,008 reviews)
"Scratching in the walls behind the bed and a terrible smell. Likely dead animal in the walls"
Reviewed on Oct 9, 2026
The Mountain Inn at Killington
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
$156 nightly
$172 total
Oct 19 - Oct 20
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
"perfect!"
Reviewed on Oct 9, 2026
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.
Find the Best Windsor Vacation Packages
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 from $779 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.