Winthrop Harbor Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NT$25,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Winthrop Harbor Vacation Packages

Winthrop Harbor Hotel Deals

LA VILLA MOTEL

LA VILLA MOTEL

2 out of 5
1401 Sheridan Rd Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
The price is NT$1,991 per night from Nov 5 to Nov 6
NT$1,991
NT$2,310 total
Nov 5 - Nov 6
includes taxes & fees
LA VILLA MOTEL
Motel Sun Inn

Motel Sun Inn

2.5 out of 5
301 Sheridan Road Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
The price is NT$1,929 per night from Nov 1 to Nov 2
NT$1,929
NT$2,238 total
Nov 1 - Nov 2
includes taxes & fees
7/10 Good! (300 reviews)
"Perfect and they have Jacuzzi"

Reviewed on 2026/10/14

Motel Sun Inn
La Quinta Inn & Suites by Wyndham Chicago Gurnee

La Quinta Inn & Suites by Wyndham Chicago Gurnee

3 out of 5
5688 Northridge Rd Gurnee IL
Fully refundableReserve now, pay when you stay
The price is NT$2,133 per night from Nov 2 to Nov 3
NT$2,133
NT$2,388 total
Nov 2 - Nov 3
includes taxes & fees
La Quinta Inn & Suites by Wyndham Chicago Gurnee
See all 677 properties in Winthrop Harbor
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.

Stay near popular Winthrop Harbor attractions

North Point Marina

Explore the waterfront in Winthrop Harbor with a trip to North Point Marina. While you're in the area, stroll along the beaches.
See properties

Frequently asked questions

How much does a Winthrop Harbor vacation package cost?
You'll find cheap prices on Expedia for your Winthrop Harbor getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Winthrop Harbor costs.
What are the cheapest months to go to Winthrop Harbor?
If you're looking to score a cheap Winthrop Harbor vacation package, consider traveling in January, February and March. You'll generally find lower rates on hotels and airfares during these quieter months — perfect for a budget-friendly break.
How many days is enough for Winthrop Harbor?
Typically, a handful of days is enough to see the major attractions during your Winthrop Harbor vacation. However, if you'd like to have some time to kick back or go on day trips, think about extending your trip.
How to find the best Winthrop Harbor package deals?
Landing a cheap Winthrop Harbor package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most economical Winthrop Harbor package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Winthrop Harbor vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and accommodations individually. Better still, you can customize your Winthrop Harbor trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Winthrop Harbor?
If you're planning an impromptu Winthrop Harbor getaway, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Winthrop Harbor?

  1. Choose your travel dates: The things you'd like to do in Winthrop Harbor and your preferred season can help you decide when to go.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and dining out to flights and experiences. Your hotel will likely be the largest expense during your trip to Winthrop Harbor.
  3. Set the duration of your trip: Start by compiling a list of the sights and activities you want to experience in Winthrop Harbor. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your airfare and accommodations: After you've settled on your dates and duration, book the right Winthrop Harbor vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.