Windsor Vacations

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Photo by William E Berry Jr.

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Find the Best Windsor Vacation Packages

Windsor Hotel Deals

Align Inn Vermont
Align Inn Vermont
2.5 out of 5
5817 Woodstock Rd, Quechee, VT
Fully refundableReserve now, pay when you stay
The price is NT$3,562 per night from Jun 22 to Jun 23
NT$3,562
NT$3,918 total
Jun 22 - Jun 23
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Excellent"

Reviewed on 2025/6/17

Align Inn Vermont
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is NT$12,669 per night from Jul 6 to Jul 7
NT$12,669
NT$15,236 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (520 reviews)
"Nice, historic vibe, a centerpiece of Woodstock."

Reviewed on 2025/6/20

Woodstock Inn & Resort
Super 8 by Wyndham White River Junction
Super 8 by Wyndham White River Junction
2 out of 5
442 North Hartland Rd, I-91 Exit 11 Rt 5 S 1/4 Mile, White River Junction, VT
Fully refundableReserve now, pay when you stay
The price is NT$2,485 per night from Jun 30 to Jul 1
NT$2,485
NT$2,734 total
Jun 30 - Jul 1
includes taxes & fees
6.4/10 (1,001 reviews)
"Place was clean and organized, staff were nice and they offer breakfast and coffee...overall very good"

Reviewed on 2025/6/20

Super 8 by Wyndham White River Junction
See all 2,596 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.

Frequently asked questions

How much does a Windsor vacation package cost?
You can pick up a vacation package to this popular destination 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?
To score cheap Windsor vacation packages, plan your trip outside of peak times like public holidays and major events. You'll generally find lower prices and better availability for hotels and flights.
How many days is enough for Windsor?
With a well-organized schedule, you can easily visit the main Windsor sights in a handful of days. But if you want to discover hidden spots or take day trips, think about booking your Windsor vacation for longer.
Is it worth booking a vacation package to Windsor?
Windsor offers everything you need for an amazing escape. Begin your Windsor vacation on a high note by visiting major attractions like South Congregational Church.
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.
How to plan a trip to Windsor?

  1. Pick your travel dates: The things you'd like to do in Windsor and your preferred season can help you decide when to get away.
  2. Budget wisely: Besides the price of your stay, you should factor in other expenses. These include food, transportation and flights. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Windsor.
  3. Determine how many days away: Start by listing all the attractions you'd like to get to in Windsor. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Windsor vacation package.

Discover the most popular places to visit in Windsor

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

The Sustainable Farmer

Enjoy an outing to The Sustainable Farmer during your stay in Windsor. Wander the riverfront in this quaint area.

The Sustainable Farmer

Old Constitution House

You can learn about the history of Windsor with a visit to Old Constitution House. Wander the riverfront in this quaint area.

Old Constitution House
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.