Windsor Vacations from $279

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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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Save 100% on your flight
Price was $397, price is now $279 per person
$279
per person
Jan 21 - Jan 24
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
Wonderful place to stay!

Reviewed on Dec 3, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Save 100% on your flight
Price was $1,634, price is now $1,245 per person
$1,245
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Very clean, everyone was so nice. Food at restaurant is a little pricey but was very good.

Reviewed on Nov 30, 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Save 100% on your flight
Price was $917, price is now $713 per person
$713
per person
Jan 21 - Jan 24
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
9.2/10 Wonderful! (549 reviews)
Top notch service. Great property and beautiful room. Went for anniversary and it did not disappoint. Romantic hotel and town

Reviewed on Nov 26, 2025

Treehouse Home in Ludlow

Treehouse Home in Ludlow

2 out of 5
Save 100% on your flight
Price was $3,507, price is now $2,731 per person
$2,731
per person
Jan 21 - Jan 24
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
No reviews
Best Western Springfield Hotel

Best Western Springfield Hotel

2.5 out of 5
Save 100% on your flight
Price was $415, price is now $324 per person
$324
per person
Jan 21 - Jan 24
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
8.8/10 Excellent! (799 reviews)
Everything was good.

Reviewed on Nov 27, 2025

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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

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

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

Windsor Hotel Deals

Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins

3 out of 5
122 Best Rd Windsor VT
$195 nightly
The price is $213 total per night from Dec 4 to Dec 5
$213 total
Dec 4 - Dec 5
Total with taxes and fees
9.6/10 Exceptional! (12 reviews)
The fat sheep farm is such a a cute cozy place. We partook in morning chores with Jay, she is absolutely amazing. She made everyone feel at home with interacting with the sheep. She was very knowledge and you can tell she genuinely loves the animals. Todd and Suzy are amazing as well. We breifly ...

Reviewed on Nov 10, 2025

Fat Sheep Farm & Cabins
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$379 nightly
The price is $417 total per night from Dec 16 to Dec 17
$417 total
Dec 16 - Dec 17
Total with taxes and fees
9.2/10 Wonderful! (552 reviews)
Top notch service. Great property and beautiful room. Went for anniversary and it did not disappoint. Romantic hotel and town

Reviewed on Nov 26, 2025

Woodstock Inn & Resort
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
$147 nightly
The price is $161 total per night from Dec 8 to Dec 9
$161 total
Dec 8 - Dec 9
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
Great staff and a beautiful place to stay

Reviewed on Nov 17, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
See all 2,607 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 $279 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.