Winslow Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Winslow

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 S$105 per night from 10 Aug to 11 Aug
S$105
10 Aug - 11 Aug
includes taxes & fees
6.8/10 (324 reviews)
Perfect for a Small Town Visit
"Safe, clean, wonderful staff, friendly people. Nice location. Walked to dinner :) Quiet."

Reviewed on 29 Jun, 2025

Super 8 by Wyndham Freeport
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 S$160 per night from 10 Aug to 11 Aug
S$160
10 Aug - 11 Aug
includes taxes & fees
8.6/10 Excellent! (348 reviews)
"I liked the proximity to other businesses in the area. Loved the breakfast the next morning! Room was a little snug between the end of the bed and the dresser."

Reviewed on 4 Jul, 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 S$128 per night from 3 Aug to 4 Aug
S$128
3 Aug - 4 Aug
includes taxes & fees
8/10 Very Good! (658 reviews)
"Ok"

Reviewed on 6 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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.