Downtown Windsor Vacations

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Price found within the past 48 hours. Click for updated prices.
  • Aug 29 - Aug 30

    Trumbull and Porter Hotel + Flight

    Corktown
    1 night
    3.5 star property
    8.4/10 - Very Good (1,066 reviews)
    "The staff was great the building is something to be desire. The halls had a odd smell to it."
    Reviewed June 3, 2026
    Roundtrip Tokyo (HND) - Detroit (DTW)
    HND - DTWNonstop DTW - HNDNonstop
    ¥264,754
    ¥249,624
    per traveler
    found 0 hours ago
    Trumbull and Porter Hotel
  • Aug 29 - Aug 30

    MotorCity Casino Hotel + Flight

    North Corktown
    1 night
    4.5 star property
    8.8/10 - Excellent (4,724 reviews)
    "Excellent gym, great location for activities and restaurants. Staff is great. Super clean and well maintained."
    Reviewed June 3, 2026
    Roundtrip Tokyo (HND) - Detroit (DTW)
    HND - DTWNonstop DTW - HNDNonstop
    ¥274,432
    ¥263,319
    per traveler
    found 0 hours ago
    MotorCity Casino Hotel
  • Aug 29 - Aug 30

    Hollywood Casino at Greektown + Flight

    Downtown Detroit
    1 night
    4.0 star property
    8.6/10 - Excellent (5,311 reviews)
    "The hotel was fine, nothing fancy, but: 1.) there's a People Mover stop in the casino, which is great UNLESS you've got a minor in your party and have to needlessly leave the building to get to it. Why would you need to travel through the casino to access it? 2.) Housekeeping by request only? Never paid as much as I did for this stay to get that kind of treatment. 3.) in 2026 there isn't a microwave in the room?"
    Reviewed June 3, 2026
    Roundtrip Tokyo (HND) - Detroit (DTW)
    HND - DTWNonstop DTW - HNDNonstop
    ¥277,907
    ¥267,198
    per traveler
    found 0 hours ago
    Hollywood Casino at Greektown
  • Aug 29 - Aug 30

    ROOST Detroit + Flight

    Downtown Detroit
    1 night
    4.5 star property
    9.8/10 - Exceptional (897 reviews)
    "One of the best hotels to stay in when in Detroit. Huge room with a kitchen so it’s great for long stays."
    Reviewed May 22, 2026
    Roundtrip Tokyo (HND) - Detroit (DTW)
    HND - DTWNonstop DTW - HNDNonstop
    ¥283,727
    ¥274,281
    per traveler
    found 0 hours ago
    ROOST Detroit
  • Aug 29 - Aug 30

    Detroit Foundation Hotel + Flight

    Downtown Detroit
    1 night
    4.0 star property
    9.4/10 - Exceptional (1,000 reviews)
    "The room was very clean. The hotel space in general seemed very clean However, the room had some weird random things- the faucet in the bathroom was loose and just kinda flopping around. The toilet paper holder was falling out of the wall. And after REALLY looking at the bathroom I noticed the trim was painted EXTREMELY messily While NONE of this was an issue with the stay - I guess I just expect more for the amount that’s paid for the room. Also the bar/restaurant (brunch on sunday) was..."
    Reviewed May 26, 2026
    Roundtrip Tokyo (HND) - Detroit (DTW)
    HND - DTWNonstop DTW - HNDNonstop
    ¥271,550
    ¥264,039
    per traveler
    found 0 hours ago
    Detroit Foundation Hotel

Where to stay in Downtown Windsor

Find the best Downtown Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Windsor

Downtown Windsor Hotel Deals

Best Western Plus Waterfront Hotel

Best Western Plus Waterfront Hotel

2.5 out of 5
277 Riverside Drive West Windsor ON
Fully refundableReserve now, pay when you stay
The price is ¥12,708 per night from Jun 14 to Jun 15
¥12,708
¥15,221 total
Jun 14 - Jun 15
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"This is our second time staying in there we love the room with the panoramic view. It’s so beautiful looking out over the Detroit river and Detroit city watching the bar just go up and down the river. It’s very entertaining. The restaurant is excellent. We enjoyed a meal there good service. All the ..."

Reviewed on Jun 3, 2026

Best Western Plus Waterfront Hotel
DoubleTree by Hilton Windsor Hotel & Suites

DoubleTree by Hilton Windsor Hotel & Suites

4 out of 5
333 Riverside Dr W Windsor ON
Fully refundableReserve now, pay when you stay
The price is ¥17,897 per night from Jun 28 to Jun 29
¥17,897
¥21,438 total
Jun 28 - Jun 29
includes taxes & fees
9.2/10 Wonderful! (1,097 reviews)
"Excellent location. Right on the Detroit River."

Reviewed on Jun 3, 2026

DoubleTree by Hilton Windsor Hotel & Suites
Holiday Inn Express Windsor Waterfront by IHG

Holiday Inn Express Windsor Waterfront by IHG

2.5 out of 5
33 Riverside Drive East Windsor ON
Fully refundable
The price is ¥15,540 per night from Jun 29 to Jun 30
¥15,540
¥18,613 total
Jun 29 - Jun 30
includes taxes & fees
8.8/10 Excellent! (1,387 reviews)
"The property was nice and the staff were kind. None of the Canadian television channels work and the rooms do not come with HDMI cords, so either bring one or prepare an alternate method."

Reviewed on Jun 3, 2026

Holiday Inn Express Windsor Waterfront by IHG
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.