Winslow Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Winslow

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 S$145 per night from 29 Dec to 30 Dec
S$145
includes taxes & fees
29 Dec - 30 Dec
8.8/10 Excellent! (738 reviews)
"Only issue was pool closure on Saturday i understand the pump shut down so closing down at some point necessary but seeing as no was in the pool until early saturday evening allowing a few hours of swimmimg would not be a health alert"

Reviewed on 18 Nov,2024

Country Inn & Suites by Radisson, Freeport, IL
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$111 per night from 26 Dec to 27 Dec
S$111
includes taxes & fees
26 Dec - 27 Dec
8/10 Very Good! (597 reviews)
"Great value. Nice breakfast. Secure. Helpful with our needs. Comfortable beds. Room condition was very good."

Reviewed on 12 Nov,2024

Baymont by Wyndham Freeport
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 S$100 per night from 9 Dec to 10 Dec
S$100
includes taxes & fees
9 Dec - 10 Dec
8.8/10 Excellent! (676 reviews)
"Staff was very helpful and friendly. Price was good for the area. The room was very quiet and comfortable. The breakfast had a good variety and stocked quickly. The only complaint was the tub appeared to have burn marks on the edge. Thanks for the nice stay."

Reviewed on 26 Nov,2024

Super 8 by Wyndham Monroe WI
See all 88 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?
Our Winslow packages, which begin at just , are the perfect way to save big. Pick and choose your preferred hotels, flights and rental car to create your ideal itinerary.
How do I get a cheap travel package to Winslow?
Creating your own Winslow holiday package with Expedia is the easiest way to save. We have access to more than 550 airlines and 1,000,000 properties globally. With such a wonderful range to choose from, you’ll have no difficulty creating your ideal adventure.
How far in advance should I book my Winslow holiday?
Travellers can normally compare international flights on Expedia within 12 months of the departure date. Booking late? With a little bit of luck, it’s still possible to purchase a cheap ticket just weeks before your journey.
What does an Expedia Winslow travel package include?
Hotels, flights and rental cars, or any combination of them — it’s your pick! Whether you’re headed to Winslow with the family or travelling with your friends, there’s a bundle to match your budget and style. Once you’ve made your booking, why not add on one or two tours or activities?
What should I know before booking a Winslow travel package?
Our prices are always low. However, you’ll grab even better deals if you book your hotels, flights and car rentals together. With an Expedia package, you’ll always get transparent pricing and a great range of choice.
Can I choose my airline with a Winslow Expedia holiday package?
Yes, definitely. Expedia has over 550 airline partners to pick from around the world. With such a big range of choice, finding the perfect carrier to take you to Winslow won’t be hard.
If I'm not able to travel, can I cancel my Winslow holiday package?
You can cancel your Winslow booking if your plans have changed. Whether you’ll incur a fee or not depends on your hotel, airline or car rental company. It may be possible to cancel or change your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

* 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.