Windsor Vacations from $787

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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.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $971, price is now $787 per person
$787
per person
Jul 20 - Jul 24
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
8.6/10 Excellent! (895 reviews)
Love the historical aspects of this place.

Reviewed on Jun 17, 2026

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $1,070, price is now $895 per person
$895
per person
Jul 20 - Jul 24
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
10/10 Exceptional! (196 reviews)
This place is amazing very unique Viking style and themed. surrounded by woods and hiking trails. They also have a special brand of sheep heard on the property. they did an exceptional job building and maintaining this place.

Reviewed on Jun 1, 2026

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $1,221, price is now $1,033 per person
$1,033
per person
Jul 19 - Jul 26
found 6 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Springfield (VSF)
8.6/10 Excellent! (855 reviews)
I’ve stayed here with my two daughters multiple times and it’s always incredible.

Reviewed on May 17, 2026

Okemo Mountain Lodging by Vail Resorts

Okemo Mountain Lodging by Vail Resorts

3.5 out of 5
Clock Tower Base Area
Price was $1,439, price is now $1,233 per person
$1,233
per person
Jul 19 - Jul 26
found 6 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.

Reviewed on Jun 26, 2025

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was $1,357, price is now $1,169 per person
$1,169
per person
Jul 19 - Jul 26
found 6 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty

Reviewed on Dec 1, 2025

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Stay near popular Windsor attractions

Bowers Covered Bridge - Vermont

Brownsville Trail

9.4/5 (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.
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Windsor Hotel Deals

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
$135 nightly
The price is $147 total per night from Jul 5 to Jul 6
$147 total
Jul 5 - Jul 6
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
"Beautiful motel. Will stay again without question."

Reviewed on Jun 17, 2026

Fireside Inn & Suites West Lebanon
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $143 total per night from Jun 28 to Jun 29
$143 total
Jun 28 - Jun 29
Total with taxes and fees
9.4/10 Exceptional! (1,223 reviews)
"Clean updated rooms"

Reviewed on Jun 17, 2026

Align Inn Vermont
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$509 nightly
The price is $560 total per night from Jun 28 to Jun 29
$560 total
Jun 28 - Jun 29
Total with taxes and fees
9.4/10 Exceptional! (586 reviews)
"If you're looking for a very comfortable stay in the quaint and historic town of Woodstock VT and don't worry about the expense, then the Woodstock Inn is the place for you!"

Reviewed on Jun 16, 2026

Woodstock Inn & Resort
See all 2,667 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 $787 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.