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Windsor Holiday

Tour the historic distillery of one of Canada’s most famous liquors and see Ontario’s largest casino in this Canadian-American border town.

Discover Windsor, the Canadian border town just across the Detroit River from Detroit’s city center, known for its heritage architecture and fine whiskeys. Windsor has long been the go-to town for Americans seeking Canada’s laxer alcohol laws. During the Prohibition era, Windsor was a liquor-smuggling hub. Today, its club strip is filled with American 19- and 20-year-olds enjoying an early first drink. Beyond the city’s exciting nightlife, Windsor is a delightful historic town, home to numerous parks and an old town district based around one of Canada’s most famous distilleries.

Find Walkerville, a historic neighborhood just south of the river that once was its own town. Walkerville is named after the American entrepreneur Hiram Walker, who founded a whiskey distillery here in 1858 and proceeded to build a town around it. Stroll through this neighborhood to find heritage buildings and Hiram Walker’s son’s lavish estate, Willistead Manor. Take a tour of the English-style country mansion in July and December.

While in Walkerville, don’t miss the Canadian Club Distillery, the whiskey distillery that started it all. Learn about the whiskey-distilling process on a tour and enjoy a whiskey sample at the tour’s end.

Explore the Windsor riverfront, where you will find a line of grassy parks with views of the Detroit skyline. Rent a bike to ride the path along the river. Tour the Dieppe Gardens, a nicely landscaped flower garden filled with monuments to the Canadian military. The nearby Odette Sculpture Park features 31 contemporary sculptures, including a silver flying saucer and a bronze elephant.

To experience Windsor’s famed nightlife, visit Caesars Windsor, a waterfront casino just across the river from Detroit’s General Motors Company headquarters. This smoke-free casino has a 27-story luxury hotel and a 24-hour poker room.

To reach Windsor, fly into Detroit’s international airport and cross the Canadian-American border via the Detroit-Windsor Tunnel. Windsor’s reputation may be wild, but it is one of Canada’s safest cities and offers plenty of family-friendly attractions.


Top Hotel Deals

See all 310 Hotels in Windsor
TownePlace Suites by Marriott Windsor

TownePlace Suites by Marriott Windsor

250 Dougall Ave, Windsor
3.6
of 5, from 148 reviews
2.5 out of 5.0

This family-friendly Windsor hotel is located in the entertainment district, within 2 mi (3 km) of Detroit Windsor Tunnel, University of Windsor, and Ambassador Bridge. Belle Isle Aquarium and Belle Isle are also within 6 mi (10 km).

£72
Best Western Plus Waterfront Hotel

Best Western Plus Waterfront Hotel

277 Riverside Drive West, Windsor
3.9
of 5, from 893 reviews
2.5 out of 5.0

Located in the heart of Windsor, this hotel is within 2 mi (3 km) of Detroit Windsor Tunnel, Ambassador Bridge, and University of Windsor. GM Renaissance Center and Ford Field are also within 6 mi (10 km).

£93
Caesars Windsor

Caesars Windsor

377 Riverside Dr E, Windsor
4.3
of 5, from 682 reviews
0.0 out of 5.0

Located in the heart of Windsor, this spa hotel is 0.6 mi (1 km) from Detroit Windsor Tunnel and within 3 mi (5 km) of Ambassador Bridge and University of Windsor. GM Renaissance Center and Ford Field are also within 6 mi (10 km).

Duck Pond Bed & Breakfast Cottage

Duck Pond Bed & Breakfast Cottage

901 Mersea Road 7, RR5, Leamington
5.0
of 5, from 3 reviews
3.5 out of 5.0

Situated in a rural location, this cottage is 4.8 mi (7.8 km) from Leamington Arts Centre and 7.9 mi (12.7 km) from Leamington Municipal Marina. Point Pelee National Park and Ciocairo Club of Windsor are also within 25 mi (40 km).

£55
Quality Inn & Suites Downtown

Quality Inn & Suites Downtown

675 Goyeau St, Windsor
2.9
of 5, from 263 reviews
2.5 out of 5.0

Located in the heart of Windsor, this hotel is 0.2 mi (0.2 km) from Detroit Windsor Tunnel and within 3 mi (5 km) of University of Windsor and Ambassador Bridge. GM Renaissance Center and Ford Field are also within 6 mi (10 km).

£64
Holiday Inn Windsor Downtown

Holiday Inn Windsor Downtown

430 Ouellette Ave, Windsor
3.3
of 5, from 123 reviews
3.0 out of 5.0

Located in the heart of Windsor, this hotel is 0.3 mi (0.5 km) from Detroit Windsor Tunnel and within 3 mi (5 km) of University of Windsor and Ambassador Bridge. GM Renaissance Center and Ford Field are also within 6 mi (10 km).

£47
Lexington Inn & Suites - Windsor ON Canada

Lexington Inn & Suites - Windsor ON Canada

2130 Division Road, Windsor
3.5
of 5, from 148 reviews
2.5 out of 5.0

Situated near the airport, this hotel is 2.1 mi (3.3 km) from Devonshire Mall and 2.4 mi (3.9 km) from Ciocairo Club of Windsor. GM Renaissance Center and Ford Field are also within 9 mi (15 km).

£43
Howard Johnson Plaza Hotel Windsor

Howard Johnson Plaza Hotel Windsor

2530 Ouellette Avenue, Windsor
2.9
of 5, from 277 reviews
2.5 out of 5.0

Situated in the business district, this hotel is 1.4 mi (2.2 km) from Devonshire Mall and 2.4 mi (3.8 km) from Detroit Windsor Tunnel. GM Renaissance Center and Ford Field are also within 6 mi (10 km).

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