Leamington Vacations from $562

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Your Leamington Vacation

With a vacation package to Leamington, say goodbye to travel planning and hello to hassle-free adventure. Every detail of your getaway has been taken care of before you depart, so you can spend more time experiencing this vibrant city. A trip to Leamington is a terrific opportunity to do some sightseeing. Be sure to look around big-name attractions such as Leamington Municipal Marina, Leamington Arts Centre and Kopegaron Woods Conservation Area. Don't put off visiting this city any longer. The ultimate Leamington vacation is only a few clicks away with Expedia.

The Latest Leamington vacation packages

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

Skye Hotel Ridgetown

2 out of 5
Price was $601, price is now $562 per person
$562
per person
Dec 15 - Dec 20
found 10 hours ago
Roundtrip flight included
Montego Bay (MBJ) to Windsor (YQG)
8/10 Very Good! (57 reviews)
Older place, very clean. Lots of hot water.

Reviewed on Nov 13, 2026

Comfort Inn Chatham

Comfort Inn Chatham

2.5 out of 5
Price was $651, price is now $618 per person
$618
per person
Dec 15 - Dec 20
found 10 hours ago
Roundtrip flight included
Montego Bay (MBJ) to Windsor (YQG)
8.8/10 Excellent! (1,002 reviews)

Towneplace Suites By Marriott Tecumseh Windsor

Towneplace Suites By Marriott Tecumseh Windsor

2.5 out of 5
Price was $879, price is now $848 per person
$848
per person
Dec 27 - Dec 29
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Windsor (YQG)
9.6/10 Exceptional! (179 reviews)

Hotel STRY

Hotel STRY

2 out of 5
Price was $1,920, price is now $1,670 per person
$1,670
per person
Dec 27 - Jan 3
found 17 hours ago
Roundtrip flight included
San Diego (SAN) to Windsor (YQG)
10/10 Exceptional! (46 reviews)
The perfect weekend getaway. From the thoughtful design choices, the spacious and well-appointed rooms, to the amazing staff, we couldn’t have had a more perfect stay. Book it! You won’t regret it!

Reviewed on Nov 11, 2026

Holiday Inn Express & Suites Windsor East - Lakeshore by IHG

Holiday Inn Express & Suites Windsor East - Lakeshore by IHG

2.5 out of 5
Price was $1,564, price is now $1,492 per person
$1,492
per person
Dec 27 - Jan 3
found 17 hours ago
Roundtrip flight included
San Diego (SAN) to Windsor (YQG)
9.6/10 Exceptional! (1,003 reviews)

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Stay near popular Leamington attractions

Point Pelee National Park

9.6/10 (480 reviews)
This southernmost tip of mainland Canada dazzles with diverse ecosystems where birds and butterflies migrate seasonally. Stroll the Marsh Boardwalk at dawn to witness wetland wildlife in their most active hours.
See properties

Leamington Hotel Deals

Days Inn by Wyndham Leamington

Days Inn by Wyndham Leamington

2.5 out of 5
201 Erie St N Leamington ON
$124 nightly
The price is $140 total per night from Nov 22 to Nov 23
$140 total
Nov 22 - Nov 23
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
"Great stay, clean room, amazing staff and good location"

Reviewed on Nov 6, 2026

Days Inn by Wyndham Leamington
Talbot Trail Inn & Suites

Talbot Trail Inn & Suites

3 out of 5
161 Talbot Street East Leamington ON
$70 nightly
The price is $79 total per night from Nov 18 to Nov 19
$79 total
Nov 18 - Nov 19
Total with taxes and fees
8.4/10 Very Good! (884 reviews)
"Door on the first room we were assigned wouldn’t open, Front desk knew there was a problem with the lock in the cooler temps. The heater in our room shut off while we were out and wouldn’t come back on after we returned. System needed to be reset , known issue if the thermostat was put up over 71 ..."

Reviewed on Nov 13, 2026

Talbot Trail Inn & Suites
Seacliffe Inn

Seacliffe Inn

3 out of 5
388 Erie Street South Leamington ON
$108 nightly
The price is $123 total per night from Dec 14 to Dec 15
$123 total
Dec 14 - Dec 15
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
"Arrived around 3:30, check-in starts at 3, no one at the desk, ring the bell for service...it took about 10 minutes for someone to show up and provide the key and some directions. Only saw one other staff member during our entire visit, on the last morning cleaning rooms. Booked here for three things...lake ..."

Reviewed on Nov 11, 2026

Seacliffe Inn
See all 364 properties in Leamington
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.

Find the Best Leamington Vacation Packages

Leamington Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Windsor Airport (YQG)
Population
33,000
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Point Pelee National Park, Leamington Municipal Marina and Hillman Marsh Conservation Area

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Frequently asked questions

How much does a Leamington vacation package cost?
You'll find cheap prices from $562 on Expedia for your Leamington break. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to Leamington costs.
What are the cheapest months to go to Leamington?
If you're hoping to book a cheap Leamington vacation package, consider visiting in November, December and January. You'll typically find lower prices on airfares and hotels during these months — ideal for budget-conscious travelers.
How many days is enough for Leamington?
Generally, a handful of days is enough to go to the top sights during your Leamington vacation. However, if you prefer to have more time to kick back or take day tours, consider extending your trip.
Is it worth booking a vacation package to Leamington?
Whether you're planning to visit attractions such as Leamington Municipal Marina and Leamington Arts Centre, or eager to experience its top-notch festivals and cycling, a Leamington vacation guarantees an unforgettable adventure. Book your getaway with Expedia and find out why Leamington is such a good vacation destination.
How to find the best Leamington package deals?
Begin your search for a Leamington package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Leamington package deal straight away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Leamington escape underway.
Is it cheaper to book a Leamington vacation as a package?
You can enjoy significant savings on your Leamington escape by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to view the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Leamington?
Enjoy fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Leamington break.
Does Expedia offer Book Now, Pay Later Leamington vacation packages?
Your Leamington trip is meant to be an escape from your busy life, not a reason for money-related stress. So to allow you a bit more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

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