Essex Holidays

Photo by Bailey Deziel

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Top hotels in Essex

Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is S$185 per night from 1 Sept to 2 Sept
S$185
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (3,030 reviews)
Oh Canada!
"Had a great stay! Only problem we encountered was the directions to the casino entrance instead of the hotel so was a bit confusing. However, security gave us great directions to the parking garage and check in! Enjoyed our stay."

Reviewed on 7 Aug, 2025

Caesars Windsor
Best Western Plus Waterfront Hotel

Best Western Plus Waterfront Hotel

2.5 out of 5
277 Riverside Drive West, Windsor, ON
Fully refundableReserve now, pay when you stay
The price is S$183 per night from 11 Aug to 12 Aug
S$183
11 Aug - 12 Aug
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"My husband and I stayed here in July 2025 for a weekend. It was close to the casino and there is also an indoor Waterpark within walking distance. It’s also walking distance to a lot of great restaurants. The room was clean and comfortable."

Reviewed on 5 Aug, 2025

Best Western Plus Waterfront Hotel
Holiday Inn Express Windsor Waterfront by IHG

Holiday Inn Express Windsor Waterfront by IHG

2.5 out of 5
33 Riverside Drive East, Windsor, ON
Fully refundable
The price is S$147 per night from 17 Aug to 18 Aug
S$147
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (1,280 reviews)
"Love the buffet breakfast"

Reviewed on 7 Aug, 2025

Holiday Inn Express Windsor Waterfront by IHG
See all 529 properties in Essex
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.

Frequently asked questions

How much does an Essex holiday package cost?
From just . Yes, you read that correctly. Our Essex holiday packages are a simple way to make your budget last longer. Bundle your favourite hotels, flights and car rentals and explore this exciting destination.
How do I get a cheap travel package to Essex?
Bundle your flights and hotels, toss in extras such as activities or a rental car, and save with an Essex holiday package. You won't just land impressive discounts on your getaway — you'll have a world of choice at your fingertips too. When you book with Expedia, you can choose from more than 550 airlines and 1,000,000 hotels around the world. Your next affordable adventure begins right here, right now!
Where should I stay in Essex?
With lots to explore in Essex, it makes sense to book a hotel near its attractions. Sprucewood Shores Estate Winery, Coopers Hawk Vineyards and Serenity Lavender Farm are some fascinating ones to put on your itinerary.
How far in advance should I book my Essex holiday?
Reward yourself with the widest variety at the cheapest prices by booking your holiday to Essex early. Air carriers generally release tickets anywhere up to a year prior to departure, so reserve your spot as soon as you can. That being said, Expedia is committed to giving you the best bargains around, so there's never a bad time to book your dream holiday!
What does an Expedia Essex travel package include?
From airfares and hotels to car rentals, Expedia can help you craft an Essex package that's perfect for you. Heading off for a while? Check out a rental car, flight and hotel bundle. If you can only squeeze in a quick getaway, a hotel and flight deal could suit you better. Tours and activities can be added after you've booked. Our holiday packages make it easy to save and plan.
What should I know before booking an Essex travel package?
An Expedia travel package can be customized for your budget and is an easy way to make your hard-earned dollars stretch further. How much you include is your call. Rental cars, hotels and flights — choose any combination that suits your style.
Can I choose my airline with an Essex Expedia holiday package?
Most definitely. We have access to over 550 airlines globally, so you can design your Essex getaway according to your budget and needs.
If I'm not able to travel, can I cancel my Essex holiday package?
Because we understand life can be unpredictable, the answer is yes. To find out more, check out our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it with no penalties. Your hotel, airline or car rental company may charge a fee if you made your booking a while ago.

Things to do

Roasting Experience at 14th Coffee Co

Roasting Experience at 14th Coffee Co

S$89
per adult
Roasting Experience at 14th Coffee Co
1-Year Windsor Essex Barrels Bottles and Brews Trail

1-Year Windsor Essex Barrels Bottles and Brews Trail

S$70
per adult
1-Year Windsor Essex Barrels Bottles and Brews Trail
7-Day Windsor Essex Barrels Bottles and Brews Trail

7-Day Windsor Essex Barrels Bottles and Brews Trail

S$37
per adult
7-Day Windsor Essex Barrels Bottles and Brews Trail
See all activities in Town of Essex

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.