Book Exclusive Essex Vacation Packages

Choose one or more items to build your trip:

Essex flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Windsor

Travelodge by Wyndham Windsor

2 out of 5
Devonshire
per person
Dec. 25 - Dec. 30
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Windsor (YQG)
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Detroit Windsor Tunnel and Caesars Windsor are located nearby.
Windsor Manor

Windsor Manor

4 out of 5
City Centre
per person
Dec. 25 - Dec. 30
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Windsor (YQG)
Stay at this 4-star apartment in Windsor. Enjoy free WiFi, patios, and premium bedding. Popular attractions MGM Grand Detroit Casino and Little Caesars Arena are located nearby.
Sandwich Boutique Hotel

Sandwich Boutique Hotel

3 out of 5
Sandwich
per person
Dec. 25 - Dec. 30
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Windsor (YQG)
Stay at this 3-star B&B in Windsor. Enjoy free WiFi, parking (surcharge), and hydromassage showerheads. Popular attractions MGM Grand Detroit Casino and Little Caesars Arena are located nearby.
The Grove Hotel

The Grove Hotel

3 out of 5
per person
Dec. 25 - Dec. 30
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Windsor (YQG)
Stay at this 3-star hotel in Kingsville. Enjoy free WiFi, free parking, and concierge services. Popular attractions Lakeside Park Walking Paths Trailhead and Pelee Island Winery are located nearby.

Top Essex hotels deals

The Grove Motel

The Grove Motel

2.5 out of 5
96 County Road 50 West, Town of Essex, ON
Free cancellation
Reserve now, pay when you stay
The price is CA $148 per night
CA $148
CA $168 total
includes taxes & fees
24 Nov - 25 Nov
Stay at this motel in Town of Essex. Enjoy free WiFi, free parking, and cable TV channels. Popular attractions Colchester Beach and Serenity Lavender Farm are located nearby.
This beautiful, clean cottage is a 4 minute walk to the beach and playground.

This beautiful, clean cottage is a 4 minute walk to the beach and playground.

Get rates
Stay at this cottage in Town of Essex. Enjoy free WiFi, a garden, and patios. Popular attractions Colchester Beach and Serenity Lavender Farm are located nearby.
Lake front escape - a quiet lake front cottage with easy access to the beach

Lake front escape - a quiet lake front cottage with easy access to the beach

Get rates
Book a stay at this beach cottage in Town of Essex. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Colchester Beach and Serenity Lavender Farm are located nearby.
Fantastic Lake View! Quiet, Clean *Deck, BBQ & Fire pit* Walk to 3 Wineries

Fantastic Lake View! Quiet, Clean *Deck, BBQ & Fire pit* Walk to 3 Wineries

Get rates
Stay at this cottage in Town of Essex. Enjoy free WiFi, a garden, and patios. Popular attractions North 42 Degrees Estate Winery and Serenity Lavender Farm are located nearby.
The Hideaway- Lake view Cottage In Wine Country

The Hideaway- Lake view Cottage In Wine Country

Get rates
Stay at this cottage in Town of Essex. Enjoy free WiFi, a garden, and patios. Popular attractions Serenity Lavender Farm and North 42 Degrees Estate Winery are located nearby.
Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is CA $145 per night
CA $145
CA $195 total
includes taxes & fees
8 Dec - 9 Dec
Stay at this 4-star business-friendly hotel in Windsor. Enjoy free WiFi, free parking, and 6 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions MGM Grand Detroit Casino and Little Caesars Arena are located nearby.
Don't see what you're looking for?
See all available properties in Essex
View all properties
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.

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. Savor the area's wineries and restaurants.

Cooper's Hawk Vineyards

Sprucewood Shores Estate Winery

5/5(1 review)

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

Oxley Estate Winery

You can enjoy a tasting or tour at Oxley Estate Winery during your travels to Town of Essex.

Oxley Estate Winery

Frequently asked questions

How much are vacation packages to Essex?
With vacation packages available from as low as CA $873, you won’t need to blow out the credit card to visit Essex. Travelocity can help. Combine experiences, flights and hotels into a convenient package and score some serious discounts. The more you book, the bigger the savings.
Where can I get the best vacation package deals for Essex?
For an affordable Essex package deal, you can’t go past Travelocity. Choose from 400 air carriers and 1,000,000 properties around the world to create your ideal escape — it’s as easy as that.
Why should I purchase my Essex vacation package with Travelocity?
Because we believe in crafting special vacation experiences. From flights and hotels to car rentals and activities, our packages make traveling a breeze. Our support team is on hand 24/7 to make sure you’ll never wander alone. We also have a Price Match Guarantee, so you can secure your getaway knowing you’ve landed the best deal around. Find a lower price and we’ll match it!
Can I save money on my Essex car rental if I combine it with hotels and flights?
You sure can. And our Essex vacation packages will help you do it. With only a few clicks you can save cash as well as time by bundling your bookings. Collect the keys to your rental car and feel the freedom of the open road. Searching for things to do? Throw some tours or experiences into your package and save on those too.
What is there to do in Essex?
You’ll feel a certain magic in the air as you wander the streets of Essex. Sprucewood Shores Estate Winery and Cooper’s Hawk Vineyards are just a couple of highlights that make this city so special, so put them on your itinerary.
Where should I stay when visiting Essex?
If you’re searching for a place to base yourself, take a look at the Adorable Guest House near EPIC Wineries!. It’s the top pick for many visitors.

Photos of local treasures

Browse Essex vacation photos for more inspiration

Photo by Bailey Deziel
Photo by Bailey Deziel
Photo by Susan Evitts
Photo by Susan Evitts
Photo by Susan Evitts
Photo by Susan Evitts