Book Exclusive Essex Vacation Packages

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Essex flight + hotel packages

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

Nicklin House

3 out of 5
per person
May 17 - May 19
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Windsor (YQG)
Stay at this 3-star guesthouse in Leamington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Dieppe Park - Legion Park Walking Path Trailhead and Leamington Arts Centre are located nearby.
Park Bungalow #4 - Seacliff Beach Suites

Park Bungalow #4 - Seacliff Beach Suites

3 out of 5
per person
May 17 - May 19
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Windsor (YQG)
Stay at this 3-star vacation home in Leamington. Enjoy free WiFi, free parking, and beach volleyball on site. Popular attractions Seacliff Park Amphitheatre and Seacliff Park are located nearby.
Coastal #1 and Cozy #2 - Seacliff Beach Suites

Coastal #1 and Cozy #2 - Seacliff Beach Suites

3.5 out of 5
per person
May 17 - May 19
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Windsor (YQG)
Stay at this 3.5-star beach guesthouse in Leamington. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Seacliff Park Amphitheatre and Seacliff Park are located nearby.
Seacliffe Inn

Seacliffe Inn

3 out of 5
per person
May 17 - May 19
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Windsor (YQG)
Stay at this 3-star beach hotel in Leamington. Enjoy free WiFi, cable TV channels, and in-room fireplaces. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Seacliff Beach and Seacliff Park are located nearby.
The Grove Hotel

The Grove Hotel

3 out of 5
per person
May 17 - May 19
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) 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 Chrysler Greenway 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 $147 per night
CA $147
CA $167 total
includes taxes & fees
27 Feb - 28 Feb
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.
Pet-friendly
Parking included
Large 5 Bed Family Home w/ Indoor Swimming Pool!

Large 5 Bed Family Home w/ Indoor Swimming Pool!

Get rates
Stay at this vacation home in Town of Essex. Enjoy air conditioning and an indoor pool. Popular attractions Colio Estate Winery and Erie Shore Vineyard are located nearby.
Pool
Kitchen
THE ESSEX HOUSE

THE ESSEX HOUSE

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Stay at this vacation home in Town of Essex. Enjoy free WiFi, a garden, and patios. Popular attractions Amherstburg-Essex Greenway Trailhead and Sadler's Nature Park Trailhead are located nearby.
Kitchen
Washer
Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is CA $152 per night
CA $152
CA $204 total
includes taxes & fees
9 Mar - 10 Mar
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 Detroit Windsor Tunnel and Ford Field are located nearby.
Pool
Parking included
DoubleTree by Hilton Windsor Hotel & Suites

DoubleTree by Hilton Windsor Hotel & Suites

4 out of 5
333 Riverside Dr W, Windsor, ON
Free cancellation
Reserve now, pay when you stay
The price is CA $165 per night
CA $165
CA $194 total
includes taxes & fees
9 Mar - 10 Mar
Book a stay at this business-friendly hotel in Windsor. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Detroit Windsor Tunnel and MGM Grand Detroit Casino are located nearby.
Pool
Pet-friendly
Holiday Inn Express Windsor Waterfront, an IHG Hotel

Holiday Inn Express Windsor Waterfront, an IHG Hotel

2.5 out of 5
33 Riverside Drive East, Windsor, ON
Free cancellation
The price is CA $143 per night
CA $143
CA $168 total
includes taxes & fees
23 Mar - 24 Mar
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Caesars Casino and Detroit Windsor Tunnel are located nearby.
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.

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

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.

North 42 Degrees Estate Winery

Frequently asked questions

How much are vacation packages to Essex?
With vacation packages available from as low as CA $516, 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