Windsor Vacation Packages

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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.

Ready to book your vacation to Windsor?

 

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Windsor Hotel Deals

Fat Sheep Farm & Cabins
Fat Sheep Farm & Cabins
3 out of 5
122 Best Rd, Windsor, VT
The price is CA $220 per night from May 1 to May 2
CA $220
CA $308 total
includes taxes & fees
May 1 - May 2
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 Jan. 18, 2025

Fat Sheep Farm & Cabins
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 CA $169 per night from May 4 to May 5
CA $169
CA $186 total
includes taxes & fees
May 4 - May 5
7.2/10 Good! (1,000 reviews)
Killington in Late April
"We had a great visit and ate in the restaurant, enjoyed the hot tub."

Reviewed on Apr. 28, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
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 CA $162 per night from May 21 to May 22
CA $162
CA $178 total
includes taxes & fees
May 21 - May 22
9/10 Wonderful! (1,003 reviews)
Best in the WRJ/Quechee/Woodstock area!
"It is the most convenient and comfortable place in the greater WRJ/Quechee/Woodstock area, with pizza and a nice restaurant/pub right next door if you tire of driving. We've stayed here before and certainly will again. Oh, and the housekeepers are great."

Reviewed on Apr. 27, 2025

Align Inn Vermont
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

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