Windsor Vacations from $724

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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
Price was $968, price is now $724 per person
$724
per person
Jan 19 - Jan 25
found 6 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Springfield (VSF)
17.6/10 Exceptional! (881 reviews)
Large, clean room with nice view. Unique.

Reviewed on Nov 9, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Save 100% on your flight
Price was $1,769, price is now $1,264 per person
$1,264
per person
Jan 19 - Jan 25
found 6 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Springfield (VSF)
17.2/10 Exceptional! (834 reviews)
Room was very clean and comfortable. Loved having the fireplace. Indoor parking garage was a plus with easy access to our room. We enjoyed dinner and breakfast at the restaurant. The outdoor space was fabulous with many activities.

Reviewed on Nov 14, 2025

Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
Clock Tower Base Area
Save 100% on your flight
Price was $3,329, price is now $2,614 per person
$2,614
per person
Jan 19 - Jan 25
found 6 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Springfield (VSF)
15.6/10 Exceptional! (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

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Save 100% on your flight
Price was $1,848, price is now $1,472 per person
$1,472
per person
Jan 19 - Jan 25
found 6 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Springfield (VSF)
18.4/10 Exceptional! (549 reviews)
Clean room, Awesome staff and always a good vibe.

Reviewed on Nov 17, 2025

Stay At Jimmy's

Stay At Jimmy's

3 out of 5
Price was $1,375, price is now $1,135 per person
$1,135
per person
Jan 19 - Jan 25
found 6 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Springfield (VSF)
20/10 Exceptional! (46 reviews)
This property is conveniently located with on site parking. It is about 10 mins walk into downtown, there are restaurants, coffee shops and ice cream shops. Room was great, everything you needed was thought of. I would recommend it very much.

Reviewed on Oct 20, 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
$193 nightly
The price is $211 total per night from Dec 7 to Dec 8
$211 total
Dec 7 - Dec 8
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
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 Nov 24 to Nov 25
$161 total
Nov 24 - Nov 25
Total with taxes and fees
7.2/10 Good! (1,003 reviews)
We love it here.

Reviewed on Nov 15, 2025

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

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$369 nightly
The price is $406 total per night from Nov 30 to Dec 1
$406 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (549 reviews)
I’ve traveled a lot around the world and this hotel has to be in my top 3 ever. Especially beautiful in autumn

Reviewed on Nov 4, 2025

Woodstock Inn & Resort
See all 2,612 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 $724 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.