Winslow Holidays

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Your Winslow Holiday

Entertainment, food, art and more … There's so much to immerse yourself in with a Winslow holiday package. And with the ability to easily customise your city adventure, it's guaranteed to be one to remember. Can't wait to see the sights but unsure where to start? Every trip to Winslow should include Lake Le Aqua Na State Park. Browse Expedia's wide range of travel options and start planning your dream holiday to Winslow now.

Winslow Holiday

Winslow Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Lake Le Aqua Na State Park, Famous Fossil Winery and Stagecoach Golf Course

Our pick of the best 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 AU$204 per night from 17 Aug to 18 Aug
AU$204
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (354 reviews)
"The room still smelled and looked new. And staff very nice."

Reviewed on 18 Jul. 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 AU$138 per night from 3 Aug to 4 Aug
AU$138
3 Aug - 4 Aug
includes taxes & fees
6.8/10 (330 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 17 Jul. 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 AU$160 per night from 3 Aug to 4 Aug
AU$160
3 Aug - 4 Aug
includes taxes & fees
8/10 Very Good! (669 reviews)
"Great"

Reviewed on 24 Jul. 2025

Baymont by Wyndham Freeport
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Winslow holiday 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 holiday 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 holiday packages and you could land some excellent off-season deals.
How many days is enough for Winslow?
With a well-organised 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 holiday 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 holiday package as early as possible.
Is it cheaper to book a Winslow holiday as a package?
You can enjoy significant savings on your next Winslow retreat by booking a tailored holiday 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 holiday 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 accommodation and airfare: Once you've nailed down your travel dates and duration, book the right Winslow holiday package for you.

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