Windsor Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Windsor Vacation

Our vacation packages to Windsor provide endless opportunities to delve into new sights, sounds and smells. And with all of the travel arrangements taken care of, you can kick back and enjoy your city escape to the fullest. Eager to do a little sightseeing? Spend your days enjoying popular attractions such as Franklin Pierce Homestead during your trip to Windsor. No matter your travel plans or budget, putting together a tailored Windsor vacation is easy with Expedia.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Coolidge

Hotel Coolidge

3 out of 5
Price was CA $1,266, price is now CA $1,177 per person
CA $1,177
per person
Jan 7 - Jan 11
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Manchester (MHT)
8.2/10 Very good! (1,007 reviews)

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $1,460, price is now CA $1,294 per person
CA $1,294
per person
Jan 7 - Jan 11
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (1,002 reviews)

The Weston

The Weston

5 out of 5
Price was CA $2,232, price is now CA $1,994 per person
CA $1,994
per person
Jan 7 - Jan 11
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
10/10 Exceptional! (12 reviews)
It’s the perfect getaway, cozy, upscale, clean. We would definitely recommend and visit again.

Reviewed on Nov 1, 2026

Deer Brook Inn

Deer Brook Inn

3 out of 5
Price was CA $1,666, price is now CA $1,523 per person
CA $1,523
per person
Jan 7 - Jan 11
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
10/10 Exceptional! (9 reviews)

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was CA $2,272, price is now CA $2,118 per person
CA $2,118
per person
Jan 7 - Jan 11
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
9.4/10 Exceptional! (620 reviews)
Absolutely beautiful hotel and property, which is a destination just in and of itself. Very comfortable, great dining options, gorgeous spa, and very walkable, if you decide to wander; Woodstock is a town right out of a Hallmark movie, after all.

Reviewed on Oct 28, 2026

Ready to book your vacation to Windsor?

 

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Windsor Hotel Deals

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Nov 9 to Nov 10
CA $135
CA $147 total
Nov 9 - Nov 10
includes taxes & fees
Days Inn by Wyndham Keene NH
Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2 out of 5
1403 New Hampshire Rte 103 Newbury NH
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Nov 11 to Nov 12
CA $159
CA $173 total
Nov 11 - Nov 12
includes taxes & fees
Hideaway Inn Mt.Sunapee
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Nov 9 to Nov 10
CA $198
CA $215 total
Nov 9 - Nov 10
includes taxes & fees
Best Western Plus Keene Hotel
See all 475 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

Stay near popular Windsor attractions

Black Pond

Commune with nature and explore the great outdoors at Black Pond during your travels in Windsor.
See properties

Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from CA $1,177 on Expedia, you'll be pleasantly surprised at how much a vacation to Windsor costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Windsor?
You're likely to find lower prices and greater availability in January, February and March. Browse our cheap Windsor vacation packages and you could score some great off-season deals.
How many days is enough for Windsor?
Generally, a handful of days is enough to tick off the main attractions during your Windsor vacation. But if you prefer to have more time to rest or go on day tours, consider extending your trip.
How to find the best Windsor package deals?
Begin your search for a Windsor package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Windsor package deal straight away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windsor getaway off to a flying start.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging hotels and flights separately. Better still, you can customize your Windsor escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Windsor?
If you've got your Windsor travel dates confirmed, book as soon as you can to score some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Windsor?

  1. Choose when to get away: Check your calendar and get packing. Your preferred season and the activities on offer will also help you decide when to vacation in Windsor.
  2. Budget wisely: As well as the price of your hotel, you'll need to consider other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected expenses that could arise during your trip to Windsor.
  3. Decide how long to go for: Now that you're more familiar with Windsor, you can figure out the perfect length of your vacation. Put together a draft itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Windsor vacation package.

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