Essex Vacations from $1,061
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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.
The Latest Essex Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Seacliffe Inn
$1,061
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Washington (DCA) to Windsor (YQG)
8.2/10 Very Good! (1,008 reviews)
the owner always welcoming the guests at the door. Warm feeling from him. The best location in leamington I belive. Room clean , bath room clean and well prepared all the stuffs necessary.
Reviewed on Aug 10, 2026
Essex Hotel Deals
The Grove Motel
96 County Rd 50 Essex ON
$138 nightly
$156 total
Aug 12 - Aug 13
Total with taxes and fees
10/10 Exceptional! (1 review)
"What a magical place! Perfectly located by the beach and the best vibes ever. If you’re looking for a spot to book- do it!!!"
Reviewed on Jul 20, 2026
Beautiful, clean cottage, 4 min walk to the beach/playground. Many wineries!
Harrow ON
9.8/10 Exceptional! (138 reviews)
"Such a wonderful visit! The cottage was neat and clean, even better in person than the photos. Early check in was a nice surprise, it allowed us to enjoy the beach for an extra day! Our 4 year old loved riding her bike over to the playground and we loved how close it was! We were told to pack light ..."
Reviewed on Aug 1, 2026
Erie Breeze Cottage, right on Lake Erie, EPIC wine route!
Essex ON
9.6/10 Exceptional! (27 reviews)
"Beautiful cottage right on the lake. Amazing views and backyard. Clean space with everything you need."
Reviewed on Jul 26, 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.
Stay near popular Essex attractions
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.
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.
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.
Oxley Estate Winery
You can enjoy a tasting or tour at Oxley Estate Winery during your travels to Town of Essex.
North 42 Degrees Estate Winery
9.6/10 (5 reviews)
You can enjoy a tasting or tour at North 42 Degrees Estate Winery during your travels to 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.
Erie Shore Vineyard
You can enjoy a tasting or tour at Erie Shore Vineyard during your travels to Town of Essex. While in this relaxing area, you can enjoy the wineries.
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.