Windsor Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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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.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
6.8/10 (1,001 reviews)
Not well maintained but the room was large

Reviewed on Jul. 9, 2025

Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Save 100% on your flight
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
9.4/10 Exceptional! (50 reviews)
We stayed off season so things in the area were sort of quiet. It is a very old facility. The room was small but clean. It was a solid room for a fair price. The gentlemen who was running the facility was very nice.

Reviewed on Apr. 23, 2025

Mountaineer Inn

Mountaineer Inn

2 out of 5
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (484 reviews)
It was ok for the price. I could hear the people walking around above me but that stopped by bedtime. The room didn’t have a refrigerator so I went to the community refrigerator but it was tiny. There were no towels in the bathroom but an automated text directed me where to find them in the hall. The volume on the tv wouldn’t go beyond 14 so it was difficult to hear, especially with the air conditioner on. The pool was not functioning and I had left my activity early so I could go for a swim. The shower was pretty good and the bed was comfortable.

Reviewed on Jul. 6, 2025

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (202 reviews)
Great property for family vacations during summer. Will return.

Reviewed on Jul. 6, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (731 reviews)
Check-in is painfully slow.

Reviewed on Jun. 24, 2025

Ready to book your vacation to Windsor?

 

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Windsor Hotel Deals

White River Inn and Suites
White River Inn and Suites
2.5 out of 5
91 Ballardvale Drive, White River Junction, VT
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Aug 10 to Aug 11
CA $155
CA $170 total
Aug 10 - Aug 11
includes taxes & fees
7/10 Good! (1,000 reviews)
"Convenient booked last minute and it had large rooms with a kitchen"

Reviewed on Jul. 1, 2025

White River Inn and Suites
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 CA $115 per night from Jul 21 to Jul 22
CA $115
CA $127 total
Jul 21 - Jul 22
includes taxes & fees
6.4/10 (1,007 reviews)
"Very kind and nice management folks.Recommend."

Reviewed on Jul. 7, 2025

Super 8 by Wyndham White River Junction
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is CA $628 per night from Aug 10 to Aug 11
CA $628
CA $752 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (523 reviews)
"Service and concierge were excellent. Property was kept in a beautiful condition. Lost of inspiring rooms."

Reviewed on Jul. 13, 2025

Woodstock Inn & Resort
See all 2,595 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Windsor

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

Frequently asked questions

How much does a Windsor vacation package cost?
You can snap up a vacation package to this destination from CA $913 on Expedia. But how much your vacation to Windsor costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Windsor?
To score cheap Windsor vacation packages, organize your trip outside of busy periods like public holidays and major events. You'll generally find better availability and lower prices for flights and hotels.
How many days is enough for Windsor?
The ideal length for your Windsor vacation depends on what you'd like to see. Usually, a few days to a week will give you enough time to go to all the leading attractions and explore some hidden spots along the way.
Is it worth booking a vacation package to Windsor?
Windsor offers everything you need for an amazing getaway. Get your Windsor vacation off to a flying start by exploring popular attractions like South Congregational Church.
How to find the best Windsor package deals?
Finding a cheap Windsor package deal is easy with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, apply some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most affordable Windsor package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away 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 tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Windsor?
If you're considering an impromptu Windsor adventure, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Windsor?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Windsor.
  2. Set your budget: Consider costs like transportation, flights and meals when calculating how much to set aside for your trip to Windsor. Then, choose a property that fits your budget, whether that's a low-cost option or a swankier getaway.
  3. Determine how many days away: Start by making a list of all the activities and sights you'd like to get to in Windsor. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Windsor vacation package that brings all your bookings together.

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