Romantic in Windsor

Windsor Romantic Hotels

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Search over a million flights, hotels, packages, and more

Featured Windsor Romantic Hotels

Image for Seacliffe Inn
3 out of 5
388 Erie Street South, Leamington, ON
Free CancellationReserve now, pay when you stay
CA $106
per night
Oct 11 - Oct 12
4.1/5Very Good! (603 reviews)

"We just got home from our over night stay at the Seacliff Inn and all I have to say is I am so glad I decided to book there. Our room was huge and so comfortable. The view from our room was perfect. We looked out towards the water, the pier and the ferry. We didn't have a chance to take advantage ..."…"

Reviewed on Sep. 14, 2019

Seacliffe Inn
Image for Drifted Inn - Riverfront Cottage
942 Front Rd S, Amherstburg, ON
Get Rates
4.8/5Exceptional! (22 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 Oct. 26, 2018

Drifted Inn - Riverfront Cottage
Image for Duck Pond Bed & Breakfast Cottage
3.5 out of 5
901 Mersea Road 7, RR5, Leamington, ON
Get Rates
5/5Exceptional! (9 reviews)

"Spacious, with an outside sitting area with view on the lawn (and the ducks). Delicious breakfast."…"

Reviewed on Sep. 14, 2019

Duck Pond Bed & Breakfast Cottage
Image for Lakeside Village Motel and Campground
2.5 out of 5
2416 Talbot Trail, Chatham-Kent, ON
Get Rates
4.3/5Excellent! (3 reviews)

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

Reviewed on Oct. 1, 2018

Lakeside Village Motel and Campground
Image for Caesars Windsor
4 out of 5
377 Riverside Dr E, Windsor, ON
CA $135
per night
Sep 30 - Oct 1
4.3/5Excellent! (2,018 reviews)

"Caesars hotels are always great, the one in Windsor though is getting old"…"

Reviewed on Sep. 18, 2019

Caesars Windsor
Image for Best Western Plus Waterfront Hotel
2.5 out of 5
277 Riverside Drive West, Windsor, ON
Free CancellationReserve now, pay when you stay
CA $104
per night
Sep 29 - Sep 30
4.1/5Very Good! (3,652 reviews)

"Good location Quick check in out Nice pool Simple breakfast Very busy elevator"…"

Reviewed on Sep. 21, 2019

Best Western Plus Waterfront Hotel
Image for Ye Olde Walkerville Bed & Breakfast
3.5 out of 5
1104 Monmouth Road, Windsor, ON
CA $116
per night
Sep 23 - Sep 24
4.7/5Exceptional! (164 reviews)

"Wonderful place, people, and staff. Highly recommended."…"

Reviewed on Sep. 3, 2019

Ye Olde Walkerville Bed & Breakfast
Image for Lexington Inn & Suites Windsor
2.5 out of 5
2130 Division Road, Windsor, ON
Free CancellationReserve now, pay when you stay
CA $66
per night
Oct 3 - Oct 4
3.7/5Good! (852 reviews)

"The facility is dated but clean. AC was noisy however the rooms were quiet.. The floors in the breakfast area were sticky and guests were walking around barefoot."…"

Reviewed on Sep. 19, 2019

Lexington Inn & Suites Windsor
Image for Wenzler's Landing Bed & Breakfast
3 out of 5
2310 Hickson Road, R1, Leamington, ON
CA $135
per night
Oct 21 - Oct 22
5/5Exceptional! (56 reviews)

"This was our first time with the Wenzlers and we hope it won’t be our last. The house is beautifully appointed and spotless. The property is beautiful with hummingbirds feeding outside the window as we ate breakfast. Deb is very kind and helpful and the breakfasts are incredible. No hotel could compare. ..."…"

Reviewed on Sep. 8, 2019

Wenzler's Landing Bed & Breakfast
Image for Four Points by Sheraton Windsor Downtown
3 out of 5
430 Ouellette Ave, Windsor, ON
Free CancellationReserve now, pay when you stay
CA $125
per night
Sep 29 - Sep 30
4.2/5Very Good! (40 reviews)

"It is a beautiful hotel. Customer service from the hotel and the restaurant was amazing. The only thing that was disappointing was the parking. Those corners were very tight and also the spots. But everything else was great,"…"

Reviewed on Sep. 16, 2019

Four Points by Sheraton Windsor Downtown
Image for Residence & Conference Centre - Windsor
2 out of 5
3995 Geraedts Drive, Windsor, ON
Get Rates
4/5Very Good! (280 reviews)

"Typical residence with all that one would (and wouldn't) expect in terms of amenities and organization."…"

Reviewed on Aug. 24, 2019

Residence & Conference Centre - Windsor
Don't see what you're looking for?
See all available properties in Windsor
View all properties
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.

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.

More trip options

Recently Booked Romantic Hotels in Windsor

Travelers Loved These Romantic Hotels