Winslow Vacations

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Find the Best Winslow Vacation Packages

Winslow Hotel Deals

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 ₩172,393 per night from Aug 17 to Aug 18
₩172,393
₩188,770 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (359 reviews)
Noisy beds
"Excellent hotel however, the beds make a horrific noise when you touch the base of them. It wakes everyone in the room, even if you’re trying to be quiet very concerning you should replace or baffle the bottom of the bed."

Reviewed on Jul 27, 2025

AmericInn by Wyndham Monroe
Super 8 by Wyndham Freeport

Super 8 by Wyndham Freeport

2 out of 5
1551 Sleezer Home Rd, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is ₩114,002 per night from Aug 3 to Aug 4
₩114,002
₩126,514 total
Aug 3 - Aug 4
includes taxes & fees
6.8/10 (331 reviews)
nicer than I expected
"I didnt go in expecting a lot, but the hotel was way nicer than I thought. Always thought "super 8" was just a cheap place, some might be, but this one was nice"

Reviewed on Jul 17, 2025

Super 8 by Wyndham Freeport
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 ₩134,717 per night from Aug 10 to Aug 11
₩134,717
₩149,508 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (672 reviews)
Good option in area
"Very nice Staff… Property a little rundown was the only reason I marked down one star. I would stay here again."

Reviewed on Jul 26, 2025

Baymont by Wyndham Freeport
See all 97 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.