Winslow Holidays
- Plan, book, travel with confidence
Better together
Save up to S$134 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top hotels in Winslow
Baymont by Wyndham Freeport
1060 Riverside Dr, Freeport, IL
The price is S$140 per night from 28 Sept to 29 Sept
S$140
28 Sept - 29 Sept
includes taxes & fees
8/10 Very Good! (686 reviews)
"We stayed in a suite with the jacuzi tub in the room. It was clean smelled doo and everything worked as it should.."
Reviewed on 12 Sept, 2025
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive, Freeport, IL
The price is S$171 per night from 28 Sept to 29 Sept
S$171
28 Sept - 29 Sept
includes taxes & fees
8.8/10 Excellent! (810 reviews)
"Dry pleasant experience. Everyone was helpful and friendly. Next time I am going to the area I will use this hotel 🏨!"
Reviewed on 13 Sept, 2025
Darlington Inn
201 Christiensen Dr, Darlington, WI
Fully refundableReserve now, pay when you stay
The price is S$111 per night from 21 Sept to 22 Sept
S$111
21 Sept - 22 Sept
includes taxes & fees
8.4/10 Very Good! (414 reviews)
Great service
"Quick trip for a day of riding on the Xhhese Trails. Darlington In let us vheck in early which was very much appreciated. The parking lot gets full quick with all the trailers but it is big enough to accommodate."
Reviewed on 31 Aug, 2025
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.
* 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.
