Essex Vacation Packages
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Your Essex Vacation
With a vacation package to Essex, say goodbye to endless planning and hello to trouble-free adventure. Every detail of your journey has been taken care of before you go, so you can enjoy each moment discovering this vibrant city. Ready for some sightseeing? A trip to Essex wouldn't be complete without checking out Amherstburg-Essex Greenway Trailhead, Sadlers Nature Park Trailhead and other top attractions. A few clicks is all it takes to craft the ideal Essex vacation on Expedia.
Top Holiday Package Deals in Essex
Price found within the past 48 hours. Click for updated prices.
Nicklin House
CA $1,095
per person
Nov 26 - Nov 29
found 8 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Windsor (YQG)
9.4/10 Exceptional! (141 reviews)
Nicklin House est un gîte touristique de grande qualité entretenu soigneusement par deux hôtes sympathiques, Paul et Dominique. On y est accueilli chaleureusement et on s'y sent presque aussitôt chez soi. Les petits déjeuners, copieux et savoureux, vous permettent de démarrer la journée avec entrain. La proximité du Parc national de la Pointe Pelée est un atout à ne pas négliger si vous aimez la nature. Bref, une étape à ne pas rater si vous passez dans cette belle région.
Reviewed on Oct 16, 2026
Hotel STRY
CA $1,255
per person
Nov 17 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Windsor (YQG)
10/10 Exceptional! (46 reviews)
This place is an oasis. The room was beautifully decorated and the bed was extremely comfortable.
I was there on business and it was still a very relaxing stay.
The staff were welcoming. The area is great for walking with lots of restaurants.
Highly recommend Hotel Stry!
Reviewed on Sep 30, 2026
Essex Hotel Deals
Erie Breeze Cottage, right on Lake Erie, EPIC wine route!
Essex ON
The Grove Motel
96 County Rd 50 Essex ON
CA $123
CA $140 total
Oct 19 - Oct 20
includes taxes & fees
Colchester cottages a stones throw away from beaches, wineries, marina, parks.
Colchester ON
9.2/10 Wonderful! (5 reviews)
"Great location and we were well cared for by our hosts. Was truly steps from the beach and there were wineries with restaurants very close by. Was quiet and secure.. cabins were newly built."
Reviewed on Aug 24, 2026
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 vacation package cost?
From just CA $1,095. Yes, you read that correctly. Our Essex vacation packages are a simple way to make your budget last longer. Bundle your favorite 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 vacation 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 vacation?
Reward yourself with the widest variety at the cheapest prices by booking your vacation 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 vacation!
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 vacation 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 vacation 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 vacation 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.
Stay near popular Essex attractions
Cooper's Hawk Vineyards
9.4/10 (3 reviews)
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
9.0/10 (4 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.
Colio Estate Winery
You can enjoy a tasting or tour at Colio Estate Winery during your travels to Harrow. While in this relaxing area, you can enjoy the wineries.
Oxley Estate Winery
You can enjoy a tasting or tour at Oxley Estate Winery during your travels to Town of Essex.
Serenity Lavender Farm
10.0/10 (2 reviews)
Enjoy an outing to Serenity Lavender Farm during your stay in Town of Essex. While in this relaxing area, you can savor the wineries and restaurants.
Amherstburg-Essex Greenway Trailhead
You can take time to visit Amherstburg-Essex Greenway Trailhead during your travels to Town of Essex.
Muscedere Vineyards
You can enjoy a tasting or tour at Muscedere Vineyards during your travels to Town of Essex. Visit the area's casinos, or simply enjoy its coffeehouses.
Sanson Estate Winery
You can enjoy a tasting or tour at Sanson Estate Winery during your travels to Town of Essex. While in this trendy area, you can enjoy the coffeehouses.
Things to do
Explore a world of travel with Expedia
- Cabin Rentals in Essex County
- Luxury Hotels in Windsor
- Cottages in Windsor
- Town of Essex Hotels
- Kingsville Hotels
- Wigle's Motel
- Colchester cottages a stones throw away from beaches
- Amherstburg Hotels
- Cottages in Leamington
- Essex County Hotels
- Motels in Windsor
- Leamington Hotels
- Essex Hotels
- Hotels with Waterslides in Essex
- Seacliffe Inn
- Hotels near Point Pelee National Park
- Beach Hotel Hotels in Essex County
- Lasalle Hotels
- Luxury Hotels in Essex County
- Tecumseh Hotels
- Best Western Plus Leamington Hotel & Conference Centre
- Cheap Hotels in Windsor
- Chatham-Kent Hotels
- Holiday Inn Express & Suites Windsor East
- Pet-Friendly Hotels in Essex
- Days Inn by Wyndham Leamington
- All Inclusive Resorts and in Essex
- Quality Inn
- 5 Star Hotels in Essex
- Windsor Hotels
- Lakeshore Hotels
- Flights from Halifax (YHZ) to Windsor (YQG)
- Flights from Calgary (YYC) to Windsor (YQG)
- Flights from Kelowna (YLW) to Windsor (YQG)
- Flights from Abbotsford (YXX) to Windsor (YQG)
- Flights from Detroit (DTW) to Windsor (YQG)
- Flights from Windsor
- Flights from Essex County
- Flights from Edmonton (YEG) to Windsor (YQG)
- Flights from Windsor
- Flights from Winnipeg (YWG) to Windsor (YQG)
- Flights to Windsor
- Flights from Ottawa (YOW) to Windsor (YQG)
- Flights from London (YXU) to Windsor (YQG)
- Flights from Montreal (YUL) to Windsor (YQG)
- Flights from Toronto (YYZ) to Windsor (YQG)
- Flights from Saskatoon (YXE) to Windsor (YQG)
- Flights from Town of Essex
- Flights from Victoria (YYJ) to Windsor (YQG)
- Flights from Kitchener (YKF) to Windsor (YQG)
- Flights from Hamilton (YHM) to Windsor (YQG)
- Flights from Sudbury (YSB) to Windsor (YQG)
- Flights from Regina (YQR) to Windsor (YQG)
- Flights from Vancouver (YVR) to Windsor (YQG)
- Sprucewood Shores Estate Winery
- Chrysler Theatre
- Leamington Vacations
- Visit Windsor
- Amherstburg Vacations
- Belle River Vacations
- Puce Vacations
- Kingston Park
- Chatham-Kent John D. Bradley Convention Centre
- Leamington Arts Centre
- The Colosseum
- Kingsville Vacations
- Kopegaron Woods Conservation Area
- Ambassador Bridge
- Adventure Bay Family Water Park
- Lakeshore Vacations
- Caesars Casino
- Detroit Windsor Tunnel
- Lasalle Vacations
- Visit Lakeshore
- Colchester Vacations
- Wheatley Provincial Park
- Dieppe Gardens
- Point Pelee National Park
- Wallaceburg & District Museum
- Wheatley Harbour
- Windsor Vacations
- Tilbury Vacations
- Pelee Island Winery
- Tecumseh Vacations
- Olde Walkerville Neighborhood
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.