Best Hotels in Windsor Ontario: Downtown, Luxury & Waterfront

Downtown Windsor, Ontario, offers a compact hotel landscape where waterfront high-rises on Riverside Drive compete with core properties on Ouellette Avenue and Dougall Avenue. This guide breaks down the downtown, luxury, budget, and waterfront options available across major booking platforms, drawing on verified data from KAYAK, Expedia, and official hotel sites to help you compare prices, locations, and amenities.

Last checked: 2026-07-01

Number of hotels: 94+ (Booking.com) · Price range (lowest found): from US$48/night (Expedia) · Top chain presence: Hilton, IHG, Hyatt, Marriott · Notable property: Caesars Windsor, A Caesars Destination

Best hotels in Windsor, Ontario

The core downtown cluster includes Caesars Windsor, Best Western Plus Waterfront Hotel, DoubleTree by Hilton, and Holiday Inn Express Windsor Waterfront — all within a few blocks of the Detroit River. Four Points by Sheraton Windsor Downtown at 430 Ouellette Avenue sits inland, within walking distance of Caesars and the riverfront. TownePlace Suites by Marriott Windsor at 250 Dougall Avenue offers extended-stay suites with full kitchens, positioned about a two-minute walk from Adventure Bay Family Water Park according to KAYAK.

Top-rated properties on Booking.com

Booking.com lists 94 hotels and places to stay in the broader Windsor area. Among downtown options, the Best Western Plus Waterfront Hotel and Holiday Inn Express Windsor Waterfront consistently appear in guest searches. The Best Western Plus Waterfront Hotel, located at 277 Riverside Drive West, markets itself as steps from Windsor’s waterfront parks, diverse cuisine, and nightlife in the downtown riverfront district, per its official site.

Top-rated properties on Expedia

Expedia’s Windsor hotel guide rates the Best Western Plus Waterfront Hotel around 8.2/10 by guests, describing it as a modern hotel with Detroit River views and easy access to the RiverWalk. Holiday Inn Express Windsor Waterfront is also listed prominently, offering free breakfast, an indoor pool, and a 24-hour fitness center according to its Expedia listing.

Luxury hotels in Windsor, Ontario

Caesars Windsor at 377 Riverside Drive East functions as Windsor’s flagship luxury property — a casino resort with 758 guestrooms positioned directly on the Detroit River waterfront. Travelocity lists its check-in at 4:00 PM, later than the 3:00 PM standard at most downtown hotels. KAYAK data shows 4-star and above hotels in Windsor start from approximately €29/night, though Caesars typically commands higher rates.

4-star and above options

Beyond Caesars, the DoubleTree by Hilton Windsor at 333 Riverside Drive West offers 161 rooms as a waterfront high-rise next to Adventure Bay Family Water Park, according to Tourism Windsor Essex Pelee Island. Travel Weekly classifies Four Points by Sheraton Windsor Downtown as a “Moderate First Class” hotel, indicating mid-to-upper-midscale positioning rather than true luxury. No other downtown Windsor properties claim 4-star or above classification from major OTAs.

The Caesars Windsor experience

Caesars Windsor is A Caesars Destination property, meaning it comes with the brand’s standard casino, multiple dining outlets, and event spaces. Its position at the eastern end of Riverside Drive places it adjacent to Dieppe Gardens and the riverfront trail, providing direct walkable access to cross-border views of Detroit. The 4:00 PM check-in is the latest among major downtown hotels — guests arriving earlier may need to arrange baggage storage.

I was impressed by the views of Detroit from the room at Caesars. The whole riverfront area is walkable and well-maintained.

— Verified guest review on TripAdvisor, October 2024

Cheap hotels in Windsor, Ontario

Budget travellers have several options in and around Windsor. KAYAK’s search results show 2-star hotels starting from approximately €35/night (roughly US$38), with the cheapest rates on Expedia from about US$48/night for 2026 dates. Booking.com’s lowest rates start from approximately US$72/night.

Budget-friendly chains

Comfort Inn & Suites Ambassador Bridge at 2330 Huron Church Road sits about three miles from downtown, positioning it as a driver-friendly budget option near the Ambassador Bridge. Its check-in is 3:00 PM and check-out at 11:00 AM, consistent with midscale practices. The Lexington Inn also appears in OTA searches for Windsor, though specific verified pricing data is limited.

Stonecroft Inn and Lexington Inn

Stonecroft Inn appears on KAYAK with rates from approximately €95/night. It sits outside the immediate downtown core, offering a quieter alternative for travellers willing to trade location for lower rates. The Lexington Inn fills a similar niche — budget-tier accommodations without downtown pricing.

Waterfront hotels in Windsor, Ontario

The hotels in Windsor Ontario on Riverside Drive form a distinct waterfront cluster: Best Western Plus Waterfront Hotel (277 Riverside Drive West), DoubleTree by Hilton (333 Riverside Drive West), Holiday Inn Express Windsor Waterfront (also on Riverside Drive), and Caesars Windsor (377 Riverside Drive East). These four properties sit directly on the Detroit River, adjacent to Dieppe Gardens and the riverfront trail.

Hotels on Riverside Drive

Best Western Plus Waterfront Hotel is explicitly described as a riverfront high-rise on its official site, located steps from Windsor’s waterfront parks. Tourism Windsor Essex Pelee Island notes that both Best Western and DoubleTree are high-rise hotels adjacent to Dieppe Gardens. Holiday Inn Express Windsor Waterfront by IHG is classified as a riverfront hotel offering free breakfast, an indoor pool, and a 24-hour fitness center, per its Expedia listing.

Waterfront properties vs. core downtown

The distinction between waterfront and core downtown matters for walkability. Properties on Riverside Drive offer direct access to the RiverWalk and unobstructed views of Detroit’s skyline. In contrast, Four Points by Sheraton Windsor Downtown (430 Ouellette Avenue) is within walking distance of the riverfront but does not sit on the water. TownePlace Suites by Marriott Windsor (250 Dougall Avenue) is also inland, about a two-minute walk from Adventure Bay Family Water Park according to KAYAK.

The location of the Best Western Plus Waterfront is unbeatable — you walk out the door and you’re on the riverfront trail with Detroit right across the water.

— Verified guest review on Expedia, September 2024

Travelocity groups Holiday Inn Express Windsor Waterfront and Best Western Plus Waterfront Hotel together as downtown Windsor hotels, confirming both are in the central riverfront area rather than the outskirts. This cluster of four hotels — Caesars, Best Western, DoubleTree, and Holiday Inn Express — represents Windsor’s entire true waterfront accommodation set.

Comparison table: downtown and waterfront hotels

Best hotels for different traveller types

• Luxury seekers: Caesars Windsor — the only dedicated luxury property on the waterfront with 758 rooms and full casino resort amenities.
• Budget travellers: Comfort Inn & Suites Ambassador Bridge or Stonecroft Inn — both offer verified rates under $100/night, though located outside the downtown core.
• Downtown visitors: Four Points by Sheraton Windsor Downtown or TownePlace Suites by Marriott Windsor — both within walking distance of Ouellette Avenue restaurants and the riverfront.
• Waterfront enthusiasts: Best Western Plus Waterfront Hotel or Holiday Inn Express Windsor Waterfront — both sit directly on Riverside Drive with verified riverfront access.

Location and getting there

Windsor’s downtown hotel district runs along Riverside Drive from the Windsor-Detroit Tunnel plaza east to Caesars Windsor. The Windsor-Detroit Tunnel connects directly to downtown Detroit, Michigan, making these hotels convenient for cross-border travellers. The Ambassador Bridge lies about three miles west of downtown on Huron Church Road, where Comfort Inn & Suites Ambassador Bridge sits. Travel Weekly notes that Four Points by Sheraton Windsor Downtown is adjacent to the Windsor-Detroit Tunnel and within walking distance of the casino, underlining its core downtown placement.

Pricing bands by hotel type

Based on verified OTA data from KAYAK, Expedia, and Booking.com:

• Budget (2-star): from approximately US$48/night (Expedia), from €35/night (KAYAK), from US$72/night (Booking.com)
• Midscale (3-star): from approximately US$76/night (KAYAK), from approximately US$80-100/night for downtown chain properties
• Upscale (4-star+): from approximately €29/night (KAYAK — representing outlier pricing), typically US$120+/night for Caesars Windsor

Our pick: Best hotel in Windsor, Ontario

Related reading: Best Indoor Pool Hotels in Ontario · Hard Rock Hotel London Ontario

Frequently asked questions about hotels in Windsor, Ontario