Winslow Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

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    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 Winslow Vacation Packages

Winslow Hotel Deals

Country Inn & Suites by Radisson, Freeport, IL

Country Inn & Suites by Radisson, Freeport, IL

2.5 out of 5
1710 South Dirck Drive Freeport IL
Fully refundable
The price is SARĀ 444 per night from Jul 26 to Jul 27
SARĀ 444
SARĀ 492 total
26 Jul - 27 Jul
includes taxes & fees
9/10 Wonderful! (914 reviews)
"Staff was very pleasant and helpful"

Reviewed on 13 July 2026

Country Inn & Suites by Radisson, Freeport, IL
Country Inn & Suites by Radisson, Stockton, IL

Country Inn & Suites by Radisson, Stockton, IL

2.5 out of 5
200 Dillon Ave Stockton IL
The price is SARĀ 331 per night from Aug 11 to Aug 12
SARĀ 331
SARĀ 367 total
11 Aug - 12 Aug
includes taxes & fees
8.4/10 Very Good! (686 reviews)
"Needs a little updating and carpet either needs to be cleaned or replaced in the hallway. Overall we were comfortable but it could use some TLC such as replace some light bulbs in the bathroom and update the bedding. Staff that did the continental breakfast were friendly and kept that room clean. ..."

Reviewed on 16 July 2026

Country Inn & Suites by Radisson, Stockton, IL
Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI

2 out of 5
500 6th St and Hwy 69 Monroe WI
Fully refundableReserve now, pay when you stay
The price is SARĀ 313 per night from Aug 9 to Aug 10
SARĀ 313
SARĀ 343 total
9 Aug - 10 Aug
includes taxes & fees
9/10 Wonderful! (879 reviews)
"Great staff"

Reviewed on 17 July 2026

Super 8 by Wyndham Monroe WI
See all 104 properties in Winslow
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.

Frequently asked questions

How much does a Winslow vacation package cost?
You'll find cheap prices on Expedia for your Winslow escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Winslow costs.
What are the cheapest months to go to Winslow?
January, February and November are great times to search for cheap Winslow vacation packages. Choosing to travel in quieter months means you'll typically find lower prices on flights and accommodations.
How to find the best Winslow package deals?
Begin your search for a Winslow package deal by entering your destination and travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Winslow package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winslow escape underway.
Is it cheaper to book a Winslow vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Winslow vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Winslow?
Score amazing discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Winslow vacation.
How to plan a trip to Winslow?

  1. Choose when to get away: Check your schedule and get packing. Your preferred season and the activities on offer will also help you decide when to visit Winslow.
  2. Set a budget: Consider costs such as flights, meals and transportation when working out how much to set aside for your trip to Winslow. Then, choose a hotel that works with your budget, whether that's an affordable option or a swankier getaway.
  3. Work out your trip length: Think about how much time you'd like to spend exploring Winslow. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Winslow vacation package that brings all your bookings together.