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Enjoy a getaway for two at these romantic properties

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Featured Windsor Romantic Hotels

See all 85 properties in Windsor
Seacliffe Inn
Seacliffe Inn
2.0 out of 5.0 388 Erie Street South, Leamington
Free Cancellation
4.1/5 (484 reviews)
C$100/ night for 2 guests

And they have a beautiful restaurant for a fine romantic dinner and the food was outta sight!

Reviewed on 18 Mar. 2018
Drifted Inn - Riverfront Cottage
Drifted Inn - Riverfront Cottage
4.9/5 (21 reviews)

This little cottage was the perfect getaway for my husband and is anniversary! The town is so cute and the cabin and everything we needed! We will come Back!

Reviewed on 26 Oct. 2018
RomanticHistoricalFamily Friendly
Duck Pond Bed & Breakfast Cottage
Duck Pond Bed & Breakfast Cottage
3.5 out of 5.0 901 Mersea Road 7, RR5, Leamington
5.0/5 (8 reviews)

Very comfortable, all needs anticipated. Lovely setting. Great food.

Reviewed on 17 Sep. 2018
Lakeside Village Motel and Campground
Lakeside Village Motel and Campground
2.5 out of 5.0 2416 Talbot Trail, Wheatley
4.3/5 (3 reviews)

Was perfect ! Very well maintained, clean and roomy Stove, fridge and kitchen were an unexpected bonus

Reviewed on 1 Oct. 2018
Caesars Windsor
Caesars Windsor
4.0 out of 5.0 377 Riverside Dr E, Windsor
4.3/5 (2,039 reviews)
C$152/ night for 2 guests

Great PLace - great locations. would stay here again!

Reviewed on 15 Feb. 2019

Recently booked Windsor hotels

Best Western Plus Waterfront Hotel
2.5 out of 5.0
Last booking: 3 hours ago
Lexington Inn & Suites - Windsor ON Canada
2.5 out of 5.0
Last booking: 6 hours ago
Caesars Windsor
4.0 out of 5.0
Last booking: 9 hours ago
Sunbridge Hotel & Conference Centre Windsor
3.0 out of 5.0
Last booking: 17 hours ago

Romantic Hotels and Accommodations in Windsor

Are you and your partner in need of a romantic vacation? Couples choose Windsor for its stunning river views and top-notch restaurants. During your trip, you might head to Detroit Windsor Tunnel, Devonshire Mall, or Ambassador Golf Club to get in some quality time exploring the sights with your significant other.

When is the Best Time to Visit Windsor?

Weather can be an important factor in your romantic holiday, so we've provided seasonal rainfall and temperature stats to help you plan your vacation:

  • Hottest months: July, August, June, and September, with an average temperature of 80°F
  • Coldest months: January, February, December, and March, with an average temperature of 20°F
  • Driest months: March, February, January, and December, with an average rainfall of 0.08 inches
  • Rainiest months: August, July, June, and May, with an average rainfall of 0.12 inches

Sightseeing in and Around Windsor

There's nothing better than wandering around a new destination with your sweetheart, so consider taking time to discover all that Windsor has to offer. If you and your partner are interested in sampling the local food and drinks, you'll love Windsor for its array of dining options and fantastic nightlife. If you want to spend a day exploring, you might consider a stop at Detroit Windsor Tunnel, Devonshire Mall, or Ambassador Golf Club.

Expedia travelers also enjoy Windsor for its:
  • Casino gaming
  • Riverfront
  • Flowers
  • Live music
  • Skyscrapers

Getting Around Windsor

Make your way to Windsor with a flight to Windsor, ON (YQG), which is the closest major airport located 4.9 mi (7.9 km) from the city center. To venture out into the surrounding area, ride aboard one of the trains from Windsor Station.