Essex Holidays

Photo by Bailey Deziel

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Essex

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 S$186 per night from 1 Dec to 2 Dec
S$186
1 Dec - 2 Dec
includes taxes & fees
8.6/10 Excellent! (3,124 reviews)
Clean and convenient

Reviewed on 14 Nov, 2025

Caesars Windsor - A Caesars Rewards Destination
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$103 per night from 7 Dec to 8 Dec
S$103
7 Dec - 8 Dec
includes taxes & fees
8/10 Very Good! (1,011 reviews)
Courteous staff, comfortable room

Reviewed on 13 Nov, 2025

Best Western Plus Waterfront Hotel
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 S$182 per night from 15 Dec to 16 Dec
S$182
15 Dec - 16 Dec
includes taxes & fees
9/10 Wonderful! (1,038 reviews)
Room was clean. I was very impressed.

Reviewed on 16 Nov, 2025

DoubleTree by Hilton Windsor Hotel & Suites
See all 533 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

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
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
Roasting Experience at 14th Coffee Co

Roasting Experience at 14th Coffee Co

S$88
per adult
Roasting Experience at 14th Coffee Co
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.