South Windsor Vacations from $630
Book a Hotel + Flight or Car together to unlock savings
The Latest South Windsor Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel STRY
Price was $1,271, price is now $1,056 per person
$1,056
per person
Jan 1 - Jan 7
found 20 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Windsor (YQG)
19.6/10 Exceptional! (20 reviews)
Absoultely enjoyed our stay. Sucess is always based on attention to details, in any business, and every detail here is well thought out. Look forward to many more visits.
Reviewed on Oct 10, 2025
Dream Estate Inn
Price was $1,035, price is now $903 per person
$903
per person
Jan 1 - Jan 7
found 20 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Windsor (YQG)
18.8/10 Exceptional! (123 reviews)
This was a lovely place to stay. The room was spacious, comfortable, ultra clean and had a little gratitude practice available to guests. While the bed and breakfast is self serve, the complementary items were healthy, easy and convenient. This is a lovely place with a lot of thoughtful touches. I highly recommend this hidden gem in Leamington Ontario.
Reviewed on Nov 5, 2025
Holiday Inn Express & Suites Windsor East - Lakeshore by IHG
Price was $995, price is now $881 per person
$881
per person
Jan 1 - Jan 7
found 20 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Windsor (YQG)
18.8/10 Exceptional! (882 reviews)
We loved our one night stay here! The beds and pillows were very comfortable, friendly staff and breakfast was full of variety and well stocked. Highly recommend! 🌟
Reviewed on Nov 17, 2025
Where to stay in South Windsor
Find the best South Windsor areas and neighborhoods for the activities you enjoy most. Learn more about South Windsor
Downtown Windsor
3 out of top 10 points of interest in this area
If you're spending some time in Downtown Windsor, Detroit Windsor Tunnel and Chrysler Theatre are top sights worth seeing.
South Windsor Hotel Deals
Stonecroft Inn
3032 Dougall Ave Windsor ON
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $119 total per night from Dec 3 to Dec 4
$119 total
Dec 3 - Dec 4
Total with taxes and fees
9.4/10 Exceptional! (1,751 reviews)
Great location and clean rooms
Reviewed on Nov 14, 2025
Comfort Inn Windsor
2955 Dougall Ave Windsor ON
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $90 total per night from Nov 30 to Dec 1
$90 total
Nov 30 - Dec 1
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Staff very pleasant. Towels and cloths for 3 adults changed regularly. Breakfast options great. Local amenities very good.
Reviewed on Nov 10, 2025
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
Windsor ON
$159 nightly
The price is $179 total per night from Nov 30 to Dec 1
$179 total
Nov 30 - Dec 1
Total with taxes and fees
10/10 Exceptional! (14 reviews)
This was an adorable small house that was spotlessly clean. Everything was labeled and had all the supplies you would need. Location was safe and in a residential area. Would stay here again. Beds were comfortable too.
Reviewed on Sep 19, 2025
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.
Discover the most popular places to visit in South Windsor
Caesars Casino
4.5/5(68 reviews)
Why not try your luck with a visit to Caesars Casino during your time in Windsor? Discover the top-notch restaurants and acclaimed theater scene in this vibrant area.
Ambassador Bridge
4.5/5(4 reviews)
You can learn about the history of Windsor with a visit to Ambassador Bridge. Stroll along the riverfront or experience the great live music in this vibrant area.
Windsor Riverfront
After visiting Windsor Riverfront, make a plan to see the other sights and activities in Windsor.
Things to do
Fun Sushi Making Class With Local Chef in Detroit
$75
per adult
Downtown Detroit Delicious Donut, Coffee, & Pastry Adventure
$70
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.