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Check availability on Winthrop Harbor Luxury Hotels

Our top choices for Winthrop Harbor luxury hotels

Breakfast, lunch, dinner served; American cuisine
Doubletree by Hilton Pleasant Prairie Kenosha

Doubletree by Hilton Pleasant Prairie Kenosha

Doubletree by Hilton Pleasant Prairie Kenosha
4.0 star property
Pleasant Prairie
8.8 out of 10, Excellent, (954)
"Staff was nice room was clean and it was very quiet"
United States
Ciara
The price is ₹8,482
₹9,627 total
includes taxes & fees
23 Dec - 24 Dec
Doubletree by Hilton Pleasant Prairie Kenosha
Exterior
DoubleTree by Hilton Libertyville - Mundelein

DoubleTree by Hilton Libertyville - Mundelein

DoubleTree by Hilton Libertyville - Mundelein
4.0 star property
Mundelein
8.6 out of 10, Excellent, (1004)
"Excellent staff, clean hotel. "
United States
Derrill
The price is ₹8,883
₹9,858 total
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Libertyville - Mundelein
Exterior
Doubletree by Hilton Hotel Racine Harbourwalk

Doubletree by Hilton Hotel Racine Harbourwalk

Doubletree by Hilton Hotel Racine Harbourwalk
4.0 star property
Historic Downtown Racine
8.4 out of 10, Very good, (1003)
"Everything was great. I will book again "
United States
Joanne
The price is ₹9,779
₹11,099 total
includes taxes & fees
11 Jan - 12 Jan 2026
Doubletree by Hilton Hotel Racine Harbourwalk
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.
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Top Winthrop Harbor Hotel Reviews

Holiday Inn Express & Suites Waukegan by IHG

Holiday Inn Express & Suites Waukegan by IHG

10/10 Excellent
"from a very friendly front desk, staff, housekeeping, hot breakfast, and cleanliness of the entire hotel, my day was extraordinary. The three women who are manning the front desk, really set the tone for my enjoyable stay. They were friendly and went out of their way to make everyone checking in. Feel welcome. The interior and exterior of the building were very well maintained and the rooms were comfortable. I could not have asked for a better time while visiting the Chicago area."
Dr. Karen 3-night trip
Posted 6 days ago
Holiday Inn Express & Suites Waukegan by IHG

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Frequently asked questions

Are you searching for the perfect hotel for your luxury holiday in Winthrop Harbor?
Use Expedia to arrange your flight to Kenosha, WI (ENW-Kenosha Regional) airport or Chicago, IL (PWK-Chicago Executive) airport, and then select from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to get what you'd like to make your stay relaxing and comfortable. If you want an upscale hotel with fine dining, a spa or several swimming pools, Expedia can assist you in finding the best luxury hotel experience that Winthrop Harbor has to offer. Winthrop Harbor has some interesting things to see and do including Lake Michigan and Winthrop Harbor Village Hall, so you might want to take in the local sights during your visit.
When can I expect good weather in Winthrop Harbor?
Planning for the weather is an important factor for making your trip to Winthrop Harbor a success, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -2°C. Average annual precipitation for Winthrop Harbor is 1045 mm.
What's there to see and do in Winthrop Harbor?
Enjoy Winthrop Harbor and visit Lake Michigan, Winthrop Harbor Village Hall and North Point Marina. If you have a little extra time during your trip, you might want to make a stop at North Point Marina Beach and Spring Bluff Forest Preserve.
How can I get around Winthrop Harbor?
It's easier to get around town in style when you know your options. If you want to explore the larger area, hop aboard a train at Winthrop Harbor Station.