Essex Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Bailey Deziel

Top hotels in Essex

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 1.769.782 ₫ per night from 4 Jan to 5 Jan
1.769.782 ₫
2.119.845 ₫ total
4 Jan - 5 Jan 2026
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Easy parking on a cold day. Staff is great. Keg next door. Was just great

Reviewed on 10 Dec 2025

Best Western Plus Waterfront Hotel
Caesars Windsor - A Caesars Rewards Destination

Caesars Windsor - A Caesars Rewards Destination

4 out of 5
377 Riverside Dr E Windsor ON
The price is 2.906.339 ₫ per night from 14 Dec to 15 Dec
2.906.339 ₫
4.020.838 ₫ total
14 Dec - 15 Dec
includes taxes & fees
8.6/10 Excellent! (3,160 reviews)
Very clean room, staff very helpfull

Reviewed on 9 Dec 2025

Caesars Windsor - A Caesars Rewards Destination
DoubleTree by Hilton Windsor Hotel & Suites

DoubleTree by Hilton Windsor Hotel & Suites

4 out of 5
333 Riverside Dr W Windsor ON
Fully refundableReserve now, pay when you stay
The price is 3.038.714 ₫ per night from 28 Dec to 29 Dec
3.038.714 ₫
3.639.771 ₫ total
28 Dec - 29 Dec
includes taxes & fees
9/10 Wonderful! (1,044 reviews)
Clean room…friendly staff…prompt response from housekeeping

Reviewed on 12 Dec 2025

DoubleTree by Hilton Windsor Hotel & Suites
See all 531 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 1null000null000 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.

Popular places to visit

Cooper's Hawk Vineyards

You can enjoy a tasting or tour at Cooper's Hawk Vineyards during your travels to Town of Essex. Savour the area's wineries and restaurants.

Cooper's Hawk Vineyards

Sprucewood Shores Estate Winery

You can enjoy a tasting or tour at Sprucewood Shores Estate Winery during your travels to Town of Essex. Discover the countryside while you're in the area.

Sprucewood Shores Estate Winery

North 42 Degrees Estate Winery

You can enjoy a tasting or tour at North 42 Degrees Estate Winery during your travels to Town of Essex. While in this relaxing area, you can savour the wineries and restaurants.

North 42 Degrees Estate Winery