Essex Vacation Packages 2025 from $951

Essex flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Caesars Windsor

City Centre

per person

Jun 8 - Jun 14

found 16 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Windsor (YQG)

A casino, 6 restaurants, and an indoor pool are all featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Relax with a drink at one of the 4 bars/lounges and enjoy perks like free self parking.

Top Essex hotels deals

The Grove Motel

96 County Road 50 West, Town of Essex, ON

Free Cancellation

Reserve now, pay when you stay

$120

includes taxes & fees

$106 per night

Mar 30 - Mar 31

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A coffee shop and a communal living room are also provided.

Pet friendly

Parking included

Large 5 Bed Family Home w/ Indoor Swimming Pool!

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An indoor pool is featured at this vacation home, along with barbecue grills.

Pool

Kitchen

THE ESSEX HOUSE

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This vacation home includes a garden and barbecue grills.

Kitchen

Washer

Caesars Windsor

377 Riverside Dr E, Windsor, ON

$145

includes taxes & fees

$121 per night

Apr 1 - Apr 2

A casino, 6 restaurants, and an indoor pool are all featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Relax with a drink at one of the 4 bars/lounges and enjoy perks like free self parking.

Pool

Parking included

DoubleTree by Hilton Windsor Hotel & Suites

333 Riverside Dr W, Windsor, ON

Free Cancellation

Reserve now, pay when you stay

$138

includes taxes & fees

$115 per night

Apr 20 - Apr 21

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

Pool

Pet friendly

Holiday Inn Express Windsor Waterfront by IHG

33 Riverside Drive East, Windsor, ON

Free Cancellation

$116

includes taxes & fees

$97 per night

Apr 20 - Apr 21

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Pool

Breakfast included

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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.

Sprucewood Shores Estate Winery

4/5(2 reviews)

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.

North 42 Degrees Estate Winery

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

Frequently asked questions

How much are vacation packages to Essex?

With vacation packages available from as low as $951, 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.