Windsor Vacations from $517

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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.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $623, price is now $517 per person
$517
per person
Sep 25 - Sep 27
found 13 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
8.6/10 Excellent! (915 reviews)
Great hotel at the best location for seeing this great town without having to drive or park. Easy walk from train station

Reviewed on Jul 17, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $2,161, price is now $1,645 per person
$1,645
per person
Sep 21 - Sep 25
found 8 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
8.8/10 Excellent! (954 reviews)
Very nice property. Would be great to have coffee in the rooms. Also very limited hot water. Ran out a few times even after a quick shower.

Reviewed on Jul 12, 2026

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $705, price is now $540 per person
$540
per person
Sep 25 - Sep 27
found 13 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
10/10 Exceptional! (200 reviews)
Beautiful place, extraordinary, Christina was so kind and accommodating.

Reviewed on Jul 15, 2026

Deer Brook Inn

Deer Brook Inn

3 out of 5
Price was $841, price is now $735 per person
$735
per person
Sep 25 - Sep 27
found 13 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
10/10 Exceptional! (2 reviews)
Our stay at the Deer Brook Inn was wonderful! From the moment we arrived and met Carmen and her family, we felt welcomed and very much at home. Our upstairs room was cozy and comfortable. The decor of the entire home is inviting and relaxed. Carmen's breakfasts are delicious and presented with great care. In addition to being a gifted cook, she is a natural as Innkeeper. Warm, gracious, attentive and interesting - an absolute delight! Meeting and spending time her was without a doubt one of the best parts of our trip. We would positively stay at Deer Brook Inn again and again.

Reviewed on Jul 13, 2026

Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $891, price is now $780 per person
$780
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Springfield (VSF)
10/10 Exceptional! (114 reviews)
Holy and Kyle were awesome! Such wonderful breakfasts each day we were there, delicious! So close to everything we wanted to see. We look forward to coming back for our next Vermont getaway!

Reviewed on Jun 19, 2026

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Stay near popular Windsor attractions

A snow-covered landscape with a wooden covered bridge over a river, surrounded by trees and a snowy path.

Brownsville Trail

9.4/10 (3 reviews)
This challenging 5.2-mile trail rewards hikers with panoramic views and the historic Norcross Quarry from the early 1900s. Pack water and wear sturdy boots for the 2,395-foot ascent through Vermont's forests.
See properties

Windsor Hotel Deals

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
$141 nightly
The price is $153 total per night from Jul 19 to Jul 20
$153 total
Jul 19 - Jul 20
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
"This is a hotel we frequent often. Comfortable rooms, breakfast is ample, great staff. We’ll be back soon."

Reviewed on Jul 17, 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
$140 nightly
The price is $154 total per night from Jul 21 to Jul 22
$154 total
Jul 21 - Jul 22
Total with taxes and fees
Align Inn Vermont
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$479 nightly
The price is $527 total per night from Aug 16 to Aug 17
$527 total
Aug 16 - Aug 17
Total with taxes and fees
9.4/10 Exceptional! (591 reviews)
"I am terribly sorry to give such a bad review. They put us in the basement they call ground level, the room smelled dank and like mold. Everything stayed wet..towels bathing suits. The people were nice. The elevator smelled like urin and puke..they charge a incidentale fee of 250 dollars a day that ..."

Reviewed on Jul 16, 2026

Woodstock Inn & Resort
See all 2,658 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 $517 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.