Windsor Vacation Packages

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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.
Hampton Inn & Suites Manchester-Bedford

Hampton Inn & Suites Manchester-Bedford

2.5 out of 5
Price was CA $1,175, price is now CA $1,080 per person
CA $1,080
per person
Oct 3 - Oct 6
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
8.4/10 Very Good! (1,003 reviews)
The beds were comfortable Carpeting in the halls were dirty

Reviewed on Aug. 17, 2025

The Centennial

The Centennial

4 out of 5
Price was CA $1,744, price is now CA $1,260 per person
CA $1,260
per person
Oct 3 - Oct 6
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
8.8/10 Excellent! (989 reviews)
Not a large chain Old nursing home

Reviewed on Aug. 20, 2025

The Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Price was CA $2,167, price is now CA $1,845 per person
CA $1,845
per person
Oct 3 - Oct 6
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
9.6/10 Exceptional! (342 reviews)
It was in a beautiful area.

Reviewed on May 30, 2025

Four Points by Sheraton Bedford Manchester Airport

Four Points by Sheraton Bedford Manchester Airport

3 out of 5
Price was CA $1,301, price is now CA $1,179 per person
CA $1,179
per person
Oct 3 - Oct 6
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
8.8/10 Excellent! (84 reviews)
Great room for the price, microwave and refrigerator and Netflix plus other streaming options. Very nice accommodations!!!

Reviewed on Aug. 14, 2025

Holiday Inn Express & Suites Merrimack by IHG

Holiday Inn Express & Suites Merrimack by IHG

2.5 out of 5
Price was CA $1,236, price is now CA $1,140 per person
CA $1,140
per person
Oct 3 - Oct 6
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
8.8/10 Excellent! (1,003 reviews)
Property was lovely.

Reviewed on Aug. 21, 2025

Ready to book your vacation to Windsor?

 

Choose your dates

Windsor Hotel Deals

Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Aug 28 to Aug 29
CA $174
CA $188 total
Aug 28 - Aug 29
includes taxes & fees
8.4/10 Very Good! (881 reviews)
"Had a great time at this location"

Reviewed on Aug. 19, 2025

Keene Elm City Hotel, Ascend Hotel Collection
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 $154 per night from Sep 1 to Sep 2
CA $154
CA $168 total
Sep 1 - Sep 2
includes taxes & fees
7/10 Good! (1,002 reviews)
"Would stay again"

Reviewed on Aug. 16, 2025

Days Inn by Wyndham Keene NH
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 $207 per night from Aug 24 to Aug 25
CA $207
CA $224 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,012 reviews)
"Clean, comfortable room, great breakfast & friendly staff."

Reviewed on Aug. 17, 2025

Best Western Plus Keene Hotel
See all 459 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

Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from CA $1,080 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.