Winslow Trips (flight + hotel)

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Top hotels in Winslow

AmericInn by Wyndham Monroe
AmericInn by Wyndham Monroe
2.5 out of 5
424 4th Ave, Monroe, WI
Fully refundableReserve now, pay when you stay
The price is P6,169 per night from Jul 6 to Jul 7
P6,169
P6,755 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (344 reviews)
"It was one of the nicer motels I’ve ever stayed in. We were given new towels when we asked for them leaving them in a bag outside the door for us and they picked up the trash bag we left outside the door. The breakfast was delicious with many options to choose from. I would definitely recommend to ..."

Reviewed on Jun 25, 2025

AmericInn by Wyndham Monroe
Baymont by Wyndham Freeport
Baymont by Wyndham Freeport
2.5 out of 5
1060 Riverside Dr, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is P4,907 per night from Jul 13 to Jul 14
P4,907
P5,446 total
Jul 13 - Jul 14
includes taxes & fees
8/10 Very Good! (652 reviews)
"Great place to stay"

Reviewed on Jun 14, 2025

Baymont by Wyndham Freeport
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 P6,316 per night from Jul 13 to Jul 14
P6,316
P7,010 total
Jul 13 - Jul 14
includes taxes & fees
8.8/10 Excellent! (787 reviews)
"Clean with friendlly staff"

Reviewed on Jun 24, 2025

Country Inn & Suites by Radisson, Freeport, IL
See all 98 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, factors like the length of stay, hotel choice and season will influence how much your vacation to Winslow costs.
What are the cheapest months to go to Winslow?
You can usually find reduced prices and better availability in January, February and November. Explore our cheap Winslow vacation packages and you could land some excellent off-season deals.
How many days is enough for Winslow?
With a well-organized travel plan, you can easily tick off the most popular Winslow sights in a few days. But if you'd like to venture off the beaten track or go on day trips, think about booking your Winslow vacation for longer.
How to find the best Winslow package deals?
Use Expedia's filter tool to find some fabulous Winslow package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Winslow package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Winslow vacation as a package?
You can enjoy significant savings on your next Winslow retreat by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Winslow?
If you have your Winslow travel dates finalized, book early to score some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Winslow?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Winslow.
  2. Plan your budget wisely: Besides the price of your stay, you'll need to consider other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that could arise during your trip to Winslow.
  3. Decide your trip length: Consider how much time you want to spend discovering Winslow. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your accommodations and airfare: Once you've nailed down your travel dates and duration, book the right Winslow 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.