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Go beyond your typical stay in Winslow

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Nov 7 - Nov 8
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Nov 8 - Nov 9
Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22

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Our top choices for Winslow hotels

A swimming pool with lounge chairs and tables, surrounded by large windows offering views of a green landscape.

1. City Express By Marriott Freeport

City Express By Marriott Freeport
3.0 star property
Freeport
8.0 out of 10, Very good, (785 reviews)
"I have been staying here for business for a few weeks. Staff has gone out of their way to be very friendly and helpful. Rooms have been clean and comfortable"
United States
Robert
$93 nightly
The price is $103
Nov 15 - Nov 16
Total with taxes and fees
City Express By Marriott Freeport
A spacious lobby with a reception desk, a fireplace, a staircase, and a seating area.

2. Country Inn & Suites by Radisson, Freeport, IL

Country Inn & Suites by Radisson, Freeport, IL
2.5 star property
Freeport
9.0 out of 10, Wonderful, (964 reviews)
"I like the little sitting areas outside the rooms."
United States
Mary kay
$103 nightly
The price is $114
Nov 22 - Nov 23
Total with taxes and fees
Country Inn & Suites by Radisson, Freeport, IL
An indoor swimming pool with a wooden ceiling, tiled walls, and a clear view of the outdoors through a window.

3. Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI
2.0 star property
Monroe
9.0 out of 10, Wonderful, (913 reviews)
"Very nice amenities for reasonably priced rooms. Very nice and helpful staff nice pool and hot tub."
United States
Kerry
$83 nightly
The price is $91
Nov 22 - Nov 23
Total with taxes and fees
Super 8 by Wyndham Monroe WI
A reception desk with a wooden finish, framed artwork on the wall, a laptop on the desk, and a coffee station to the right.

4. Country Inn & Suites by Radisson, Stockton, IL

Country Inn & Suites by Radisson, Stockton, IL
2.5 star property
Stockton
8.2 out of 10, Very good, (724 reviews)
"This was a great stay! Everything was very clean and the staff was wonderful!"
United States
Samantha
$64 nightly
The price is $71
Nov 29 - Nov 30
Total with taxes and fees
Country Inn & Suites by Radisson, Stockton, IL
A modern bar area with a long counter, multiple beverage dispensers, and a seating arrangement with colorful chairs.

5. Hampton Inn Freeport

Hampton Inn Freeport
2.5 star property
Freeport
8.8 out of 10, Excellent, (495 reviews)
"Breakfast buffet was good"
United States
Debi
$98 nightly
The price is $108
Nov 22 - Nov 23
Total with taxes and fees
Hampton Inn Freeport
A spacious kitchen area with a long counter, wooden cabinets, and a large window offering a view of the outdoors.

6. AmericInn by Wyndham Monroe

AmericInn by Wyndham Monroe
3.0 star property
Monroe
8.8 out of 10, Excellent, (425 reviews)
"Great place"
United States
Brian
$121 nightly
The price is $133
Nov 15 - Nov 16
Total with taxes and fees
AmericInn by Wyndham Monroe
A multi-story hotel with a beige facade, a covered entrance, and a parking lot with cars.

7. Super 8 by Wyndham Freeport

Super 8 by Wyndham Freeport
2.0 star property
Freeport
7.0 out of 10, Good, (400 reviews)
"Breakfast was great! Air con worked and was tidy."
Australia
Charles
$89 nightly
The price is $99
Dec 7 - Dec 8
Total with taxes and fees
Super 8 by Wyndham Freeport
A swimming pool with a 3-foot depth marker, tiled edges, and a drain in the center.

8. Darlington Inn

Darlington Inn
2.0 star property
Darlington
8.6 out of 10, Excellent, (452 reviews)
"Love the place for utv riding, the pool and hot tub and the breakfast are all great"
United States
Paul
$89 nightly
The price is $97
Nov 8 - Nov 9
Total with taxes and fees
Darlington Inn
A hotel lobby with a reception desk, seating area with chairs, a potted plant, and a view of the street through the glass doors.

9. Eugene Hotel

Eugene Hotel
2.0 star property
Monroe
9.4 out of 10, Exceptional, (44 reviews)
"Very nice rooms, right by the town square. Definitely would stay again!"
United States
James
$105 nightly
The price is $115
Nov 15 - Nov 16
Total with taxes and fees
Eugene Hotel
A kitchen counter with a coffee maker, frying pan, and a tablet.

10. Straw clay sauna house on organic farm

Straw clay sauna house on organic farm
Mount Horeb
9.6 out of 10, Exceptional, (60 reviews)
"A low key, simple, straw house cottage with the necessary basic amenities for a quite meditative stay. The standout is the wood stove-heated sauna & European-style cold plunge pool, both inside the cottage. If you love to sauna & cold-water plunge this is the place."
United States
Michael
$206 nightly
The price is $218
Nov 8 - Nov 9
Total with taxes and fees
Straw clay sauna house on organic farm
A reception desk with a clock, a calendar, and a framed artwork on the wall.

11. West Motel

West Motel
2.0 star property
Freeport
7.0 out of 10, Good, (14 reviews)
"It was perfect clean and peaceful"
United States
Megan
$70 nightly
The price is $78
Dec 8 - Dec 9
Total with taxes and fees
West Motel
A building with a flag, a sign for 'Apple Canyon', and a parking area with golf carts.

12. Spacious Suite w/ 2 King Beds | Near Trails, Lake & Golf

Spacious Suite w/ 2 King Beds | Near Trails, Lake & Golf
Apple River
9.6 out of 10, Exceptional, (9 reviews)
"Was close to lake and clean "
United States
Hunter O.
Spacious Suite w/ 2 King Beds | Near Trails, Lake & Golf
A cozy living room with a fireplace, a sofa, a dining table, and a kitchen area visible through an open door.

13. Jaggi Swiss Gasthaus

Jaggi Swiss Gasthaus
Monticello
10.0 out of 10, Exceptional, (48 reviews)
"Enjoyed our stay"
United States
Laura A.
Jaggi Swiss Gasthaus
A spacious room with a large bed, wooden ceiling, and a cozy seating area with a sofa and a table.

14. The Dairy at the Wegmueller Farm - stay on a Wisconsin farm!

The Dairy at the Wegmueller Farm - stay on a Wisconsin farm!
Monroe
10.0 out of 10, Exceptional, (18 reviews)
"The stay at the farm was great! Everyone especially enjoyed the pigs and cows! Highly recommend! "
United States
Trish T.
The Dairy at the Wegmueller Farm - stay on a Wisconsin farm!
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.
View all properties

Compare top hotels in Winslow

A swimming pool with lounge chairs and tables, surrounded by large windows offering views of a green landscape.

City Express By Marriott Freeport

3.0 star property
Freeport
View
A spacious lobby with a reception desk, a fireplace, a staircase, and a seating area.

Country Inn & Suites by Radisson, Freeport, IL

2.5 star property
Freeport
View
An indoor swimming pool with a wooden ceiling, tiled walls, and a clear view of the outdoors through a window.

Super 8 by Wyndham Monroe WI

2.0 star property
Monroe
View
A reception desk with a wooden finish, framed artwork on the wall, a laptop on the desk, and a coffee station to the right.

Country Inn & Suites by Radisson, Stockton, IL

2.5 star property
Stockton
View
A modern bar area with a long counter, multiple beverage dispensers, and a seating arrangement with colorful chairs.

Hampton Inn Freeport

2.5 star property
Freeport
View
8.0
Very good
785 reviews
9.0
Wonderful
964 reviews
9.0
Wonderful
913 reviews
8.2
Very good
724 reviews
8.8
Excellent
495 reviews
$93 nightly
The price is $103
Nov 15 - Nov 16
Total with taxes and fees
$103 nightly
The price is $114
Nov 22 - Nov 23
Total with taxes and fees
$83 nightly
The price is $91
Nov 22 - Nov 23
Total with taxes and fees
$64 nightly
The price is $71
Nov 29 - Nov 30
Total with taxes and fees
$98 nightly
The price is $108
Nov 22 - Nov 23
Total with taxes and fees
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • No Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet friendly
  • No WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet friendly
  • No WiFi included
  • Yes, Parking

Top Winslow Hotel Reviews

An indoor swimming pool with a wooden ceiling, tiled walls, and a clear view of the outdoors through a window.
Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI
Monroe

10/10 Excellent

The beds were very comfortable. The room was clean. The staff very pleasant.
United States
Tami
Reviewed April 29, 2025
Super 8 by Wyndham Monroe WI

Frequently Asked Questions

What's the top vacation rental that Winslow has to offer?

Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond: Visitors like this Winslow vacation home rental. It is located in a rural location and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. See all vacation rentals in Winslow.

If I need to cancel my hotel reservation in Winslow, will I receive a refund?

Yes, you'll find most hotel reservations are refundable provided that you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your check-in date. If you have a reservation that's non-refundable, you might still have the option to cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winslow.

Where can I learn more about changing or cancelling my trip to Winslow?

For more information about rescheduling or cancelling your trip to Winslow, go to https://www.expedia.com/service/.

How is it to stay in Winslow?

Travelers to Winslow will find plenty to explore and enjoy. There are 98 hotels and other accommodations in the surrounding area. Find out more about Winslow.

What should I see while I'm in Winslow?

Places to visit in the wider area include Lake Le Aqua Na State Park, National Historic Cheesemaking Center Museum, and Minhas Craft Brewery. You'll also find Apple River Canyon State Park and Apple River in the area. Check out what more to see and do in Expedia's Winslow guide.

What's the weather like in Winslow?

The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Winslow are January, December, March, and April, with each month seeing an average of 8 inches of snowfall.

Where is the best place for a stay in Winslow?

Located 14.5 mi (23.3 km) from the heart of Winslow, City Express By Marriott Freeport is a top choice for your stay based on our traveler data. Other good choices for your stay in the area are Country Inn & Suites by Radisson, Freeport, IL and Eugene Hotel. See all available top hotels, or vacation rentals in Winslow.

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