Windsor Vacations from $525

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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.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was $590, price is now $525 per person
$525
per person
May 4 - May 7
found 20 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
8.8/10 Excellent! (242 reviews)
Staff was great, location terrific, restaurant/bar very nice, room was really nice, kitchen well equipped

Reviewed on Jan 19, 2026

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $646, price is now $555 per person
$555
per person
May 4 - May 7
found 20 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Clean, staff was great.

Reviewed on Dec 23, 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $945, price is now $868 per person
$868
per person
May 4 - May 7
found 20 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
9.2/10 Wonderful! (549 reviews)
Excellent hotel, staff well trained.

Reviewed on Jan 21, 2026

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Discover the most popular places to visit in Windsor

Bowers Covered Bridge - Vermont

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
La rivière Otter Creek pour aller à Vergennes, Vermont.

Paradise Park

4/5(4 reviews)

Explore the great outdoors at Paradise Park, a lovely green space in Windsor. Wander the riverfront in this quaint area.

Paradise Park

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

Windsor Hotel Deals

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $172 total per night from Mar 1 to Mar 2
$172 total
Mar 1 - Mar 2
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
Close to the resort, nice hot tub, decent room with a modern tv software for easy connections. Good price to hotel quality ratio.

Reviewed on Jan 26, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
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
$133 nightly
The price is $145 total per night from Feb 22 to Feb 23
$145 total
Feb 22 - Feb 23
Total with taxes and fees
8.2/10 Very Good! (1,006 reviews)
Environment, upgraded room and food

Reviewed on Feb 8, 2026

Fireside Inn & Suites West Lebanon
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
$105 nightly
The price is $115 total per night from Feb 22 to Feb 23
$115 total
Feb 22 - Feb 23
Total with taxes and fees
9.2/10 Wonderful! (1,102 reviews)
Very clean room, kind staff and excellent breakfast.

Reviewed on Feb 6, 2026

Align Inn Vermont
See all 2,698 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.

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 $525 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.