Windsor Vacations from $712

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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, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $841, price is now $712 per person
$712
per person
Jul 1 - Jul 5
found 1 hour ago
Roundtrip flight included
Houston (HOU) to Springfield (VSF)
8.6/10 Excellent! (851 reviews)
No inflatable mattress offered anymore.

Reviewed on Mar 18, 2026

Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $1,320, price is now $930 per person
$930
per person
Jun 15 - Jun 19
found 14 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Springfield (VSF)
10/10 Exceptional! (110 reviews)
Clean and cozy room, excellent breakfast, and very friendly host.

Reviewed on Feb 22, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,357, price is now $1,037 per person
$1,037
per person
Jul 1 - Jul 5
found 1 hour ago
Roundtrip flight included
Houston (HOU) to Springfield (VSF)
8.8/10 Excellent! (917 reviews)
Everything was great.

Reviewed on Apr 8, 2026

Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
West Woodstock
Price was $880, price is now $721 per person
$721
per person
Jul 1 - Jul 5
found 1 hour ago
Roundtrip flight included
Houston (HOU) to Springfield (VSF)
8.6/10 Excellent! (65 reviews)
Super friendly and knowledgeable staff. The Inn is historic, in a lovely spot, and reasonably priced. Dining recommendations were spot on.

Reviewed on Apr 12, 2026

The Vesper

The Vesper

3 out of 5
Price was $980, price is now $812 per person
$812
per person
Jul 1 - Jul 5
found 1 hour ago
Roundtrip flight included
Houston (HOU) to Springfield (VSF)
9.2/10 Wonderful! (57 reviews)
Uniqueness of rooms, breakfast options and walking distance to so many great spots!

Reviewed on Feb 18, 2026

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Discover the most popular places to visit in Windsor

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
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

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
$139 nightly
The price is $152 total per night from Apr 19 to Apr 20
$152 total
Apr 19 - Apr 20
Total with taxes and fees
7.4/10 Good! (1,000 reviews)
it was good

Reviewed on Apr 8, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
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
$115 nightly
The price is $126 total per night from May 3 to May 4
$126 total
May 3 - May 4
Total with taxes and fees
7/10 Good! (1,002 reviews)
Friendly staff. Great breakfast selection

Reviewed on Apr 13, 2026

White River Inn and Suites
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
$126 nightly
The price is $137 total per night from May 10 to May 11
$137 total
May 10 - May 11
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
Definitely more of a motel than a hotel. Older rooms and decor. I did not use any amenities or even eat breakfast. I was on the first floor surrounded by a very large group of families with small children. Children were running, screaming and crying the entire stay. One child cried at the top of ...

Reviewed on Apr 13, 2026

Fireside Inn & Suites West Lebanon
See all 2,689 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 $712 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.