Windsor Vacations

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Find the Best Windsor Vacation Packages

Windsor Hotel Deals

Fat Sheep Farm & Cabins
Fat Sheep Farm & Cabins
3 out of 5
122 Best Rd, Windsor, VT
The price is SAR 596 per night from Mar 31 to Apr 1
SAR 596
SAR 834 total
includes taxes & fees
31 Mar - 1 Apr
9.6/10 Exceptional! (9 reviews)
I didn’t wanna leave
"Honestly as soon as I got there I knew I had made a good choice. Then I stepped into the cabin and knew I had made an excellent choice. It’s by far the cleanest place Ive stayed. I went looking for peace and quiet and I got just that. It’s silent, it’s beautiful, it’s private. Even though it’s deep ..."

Reviewed on 18 January 2025

Fat Sheep Farm & Cabins
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 SAR 408 per night from Apr 13 to Apr 14
SAR 408
SAR 449 total
includes taxes & fees
13 Apr - 14 Apr
9/10 Wonderful! (1,003 reviews)
"We were there off season and it was delightful. We would love to go back in the fall!"

Reviewed on 26 March 2025

Align Inn Vermont
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is SAR 1,122 per night from Apr 6 to Apr 7
SAR 1,122
SAR 1,399 total
includes taxes & fees
6 Apr - 7 Apr
9.2/10 Wonderful! (505 reviews)
Perfect Spot
"The Woodstock Inn & Resort is the quintessential New England inn. Walk in the lobby and you are greeted by a large warm fire. The staff at all levels were gracious and helpful. The room was large, well decorated and extremely comfortable. Great location to walk downtown even with single digit temperatures. ..."

Reviewed on 22 February 2025

Woodstock Inn & Resort
See all 2,621 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 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

Harpoon Brewery

4.5/5(5 reviews)

You can take time to visit Harpoon Brewery during your travels to Windsor. Wander the forest or discover the area's mountain views.

Harpoon Brewery

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

South Congregational Church

Find out about the history of Windsor with a stop at South Congregational Church. Wander the riverfront in this quaint area.

South Congregational Church