Windsor Vacations from $616

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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 $761, price is now $616 per person
$616
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
First room we checked into was not cleaned but staff was quick to get us a new room. New room had a great view of the river and was clean enough. We only had about half a roll of toilet paper in the family room and no spares. Also no phone in the room to call the office. A good place to lay your head but not much more.

Reviewed on Jan 11, 2026

The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $841, price is now $667 per person
$667
per person
Feb 20 - Feb 24
found 9 hours ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
7.6/10 Good! (1,002 reviews)
Easy check in and good parking

Reviewed on Jan 9, 2026

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $1,135, price is now $927 per person
$927
per person
Mar 19 - Mar 23
found 1 day 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

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $919, price is now $752 per person
$752
per person
Feb 20 - Feb 24
found 9 hours ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
8.4/10 Very Good! (822 reviews)
Room was very clean and the hotel staff were very friendly! Hotel is attached to a movie theater which is great!

Reviewed on Dec 31, 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,234, price is now $1,023 per person
$1,023
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
9.2/10 Wonderful! (549 reviews)
Luxurious and friendly resort! Loved it

Reviewed on Dec 18, 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

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

White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive White River Junction VT
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $124 total per night from Feb 8 to Feb 9
$124 total
Feb 8 - Feb 9
Total with taxes and fees
6.8/10 (1,006 reviews)
Great hotel! Beautiful area

Reviewed on Jan 12, 2026

White River Inn and Suites
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
$163 nightly
The price is $180 total per night from Jan 20 to Jan 21
$180 total
Jan 20 - Jan 21
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
Solid accommodations.

Reviewed on Jan 12, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
$261 nightly
The price is $288 total per night from Jan 19 to Jan 20
$288 total
Jan 19 - Jan 20
Total with taxes and fees
9.2/10 Wonderful! (980 reviews)
Check in service Breakfast

Reviewed on Jan 14, 2026

The Mountain Inn at Killington
See all 2,652 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 $616 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.