Windsor Vacations from $1,388

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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.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $1,562, price is now $1,388 per person
$1,388
per person
Apr 6 - Apr 10
found 6 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Clean, staff was great.

Reviewed on Dec 23, 2025

Treehouse Home in Ludlow

Treehouse Home in Ludlow

2 out of 5
Price was $3,381, price is now $2,822 per person
$2,822
per person
Apr 6 - Apr 10
found 6 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
No reviews
Luxury 6br Solitude Ge- Indoor Bball Court, Private Tub 6 Bedroom Home by RedAwning

Luxury 6br Solitude Ge- Indoor Bball Court, Private Tub 6 Bedroom Home by RedAwning

3.5 out of 5
Save 100% on your flight
Price was $10,143, price is now $9,053 per person
$9,053
per person
Apr 6 - Apr 10
found 6 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
No reviews
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
Price was $1,743, price is now $1,555 per person
$1,555
per person
Apr 6 - Apr 10
found 6 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
8.8/10 Excellent! (25 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

Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
Price was $1,661, price is now $1,491 per person
$1,491
per person
Apr 6 - Apr 10
found 6 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
8/10 Very Good! (31 reviews)
Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also.

Reviewed on Oct 8, 2025

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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

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
7.4/10 Good! (1,003 reviews)
Hot tub, location, and breakfast.

Reviewed on Feb 18, 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
$139 nightly
The price is $151 total per night from Mar 1 to Mar 2
$151 total
Mar 1 - Mar 2
Total with taxes and fees
8.2/10 Very Good! (1,004 reviews)
Last night was the worst hotel experience I have ever had - I am not exaggerating. After staying at the Fireside inn in West Leb 2-3 nights a month for the last several months, I will not be returning. I have never been as insulted as I was by their front desk staff person as I was last night. This ...

Reviewed on Feb 18, 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
$108 nightly
The price is $119 total per night from Feb 22 to Feb 23
$119 total
Feb 22 - Feb 23
Total with taxes and fees
9.4/10 Exceptional! (1,114 reviews)
Great staff location great breakfast, all around . 5 stars for me any day ,

Reviewed on Feb 17, 2026

Align Inn Vermont
See all 2,696 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 $1,388 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.