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 AED 584 per night from Apr 10 to Apr 11
AED 584
AED 817 total
includes taxes & fees
10 Apr - 11 Apr
9.6/10 Exceptional! (8 reviews)
"Excellent. It had everything we needed"

Reviewed on 29 January 2024

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 AED 403 per night from Apr 13 to Apr 14
AED 403
AED 444 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
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
The price is AED 509 per night from Apr 28 to Apr 29
AED 509
AED 560 total
includes taxes & fees
28 Apr - 29 Apr
7.2/10 Good! (1,000 reviews)
"We loved the staff at the hotel and how smooth the check in and check out was. The property is clean and convenient with a restaurant and a bar. There is a nice common area and a spacious hot tub."

Reviewed on 17 March 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
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