Book Hotels in Winslow, IL

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Top Winslow hotels

Beautiful compound, 10 mile views, on 300 acre ranch, next to Galena Territory

Beautiful compound, 10 mile views, on 300 acre ranch, next to Galena Territory

Elizabeth
This vacation home features a gym and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.
Family trip
"We had a great stay! Check in was incredibly easy, there was lots of entertainment for the kids ages 3-14, and it was great having access to the Owners Club in the Galena Territory."

Reviewed on Aug 11, 2025

Get rates
Opens in a new windowBeautiful compound, 10 mile views, on 300 acre ranch, next to Galena Territory
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
$125 nightly
The price is $139 total per night from Oct 26 to Oct 27
$139 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features an indoor pool and a gym. Enjoy the hot tub and free perks like full breakfast and free self parking. A business center, free WiFi in public ...
"Clean"

Reviewed on Sep 25, 2025

Opens in a new windowCountry Inn & Suites by Radisson, Freeport, IL
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
$82 nightly
The price is $89 total per night from Oct 19 to Oct 20
$89 total
Oct 19 - Oct 20
Total with taxes and fees
This motel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and ...
"We stay at this location at least once per year. It is always a plesure to visit because everything is absolutely perfect. From the smooth and effortless check-in to a clean and safe room to checking out with "Please stay with us again" make the the VERY BEST Super 8 that we have EVER stayed in ..."

Reviewed on Sep 28, 2025

Opens in a new windowSuper 8 by Wyndham Monroe WI
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
$125 nightly
The price is $137 total per night from Oct 2 to Oct 3
$137 total
Oct 2 - Oct 3
Total with taxes and fees
This hotel features an indoor pool and a hot tub. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like ...
"I didnt like that it had no elevator to the second floor. One night with a lot of pick ups and trailers which one took 4 parking spaces including handicapped space. The breakfast was exceptional. Nice clean room. Quiet. Had quite a few fast food places and nice restaurants within walking distances. ..."

Reviewed on Sep 23, 2025

Opens in a new windowAmericInn by Wyndham Monroe
Hampton Inn Freeport

Hampton Inn Freeport

2.5 out of 5
109 S Galena Ave, Freeport, IL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $122 total per night from Oct 26 to Oct 27
$122 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free perks like buffet breakfast and free self parking. A business center, ...
"Very quiet. The ice machines didnt work"

Reviewed on Sep 20, 2025

Opens in a new windowHampton Inn Freeport
Country Inn & Suites by Radisson, Stockton, IL

Country Inn & Suites by Radisson, Stockton, IL

2.5 out of 5
200 Dillon Ave, Stockton, IL
$81 nightly
The price is $90 total per night from Oct 28 to Oct 29
$90 total
Oct 28 - Oct 29
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate ...
"Staff was very attentive and quick to respond to our requests for my handicapped husband. Would definitely stay again."

Reviewed on Sep 25, 2025

Opens in a new windowCountry Inn & Suites by Radisson, Stockton, IL
Darlington Inn

Darlington Inn

2 out of 5
201 Christiensen Dr, Darlington, WI
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $86 total per night from Oct 5 to Oct 6
$86 total
Oct 5 - Oct 6
Total with taxes and fees
This motel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
"Our check in was easy n the receptionist was great to deal with. We had a pretty easy time finding parking for our truck n 20 ft trailer we were pulling. Our room was very clean and inviting. We will definitely stay again."

Reviewed on Sep 29, 2025

Opens in a new windowDarlington Inn
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
$102 nightly
The price is $113 total per night from Oct 26 to Oct 27
$113 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental ...
"The carpets were dirty. The staff said they were going to get the place upgraded soon"

Reviewed on Sep 25, 2025

Opens in a new windowBaymont by Wyndham Freeport
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.

Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.

Elizabeth
$5,902 nightly
The price is $6,255 total per night from Oct 8 to Oct 9
$6,255 total
Oct 8 - Oct 9
Total with taxes and fees
This vacation home features an outdoor pool and an indoor pool. A hot tub and laundry facilities are also provided.
Excellent Retreat Experience
"This property offers the luxury of a resort with the down-home experience of a ranch. Peaceful, gorgeous views - especially at sunset from the "Quiet Rock" deck. Or the sunrise from the swing near the Main Lodge. Mark is a gracious host who shared his love of the property by introducing us to Waffles, ..."

Reviewed on Oct 7, 2024

Opens in a new windowLuxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
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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

What are the top kid-friendly hotels in Winslow?
Family getaways are where the best memories are made, but it's no secret that traveling with children can be demanding. These kid-friendly Winslow hotels come with perks designed to keep young and old alike relaxed and happy: Country Inn & Suites by Radisson, Stockton, IL will help make your adventure the most memorable one yet. It offers a variety of conveniences aimed at families, such as a swimming pool and complimentary breakfast. Alternatively, spend your Winslow escape at Baymont by Wyndham Freeport. Take advantage of a swimming pool, complimentary breakfast and more here.
Where can I find cheap hotels in Winslow?
At Travelocity you'll find really nice hotels in Winslow at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winslow rather than in Winslow. We may find you even better rates, too.
How do I find the best Winslow hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Winslow then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Winslow?
The cheapest hotel in Winslow is $86. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Winslow?
There are 98 hotels in Winslow on Travelocity.
What are the best hotels in Winslow?
Winslow has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winslow for you!
When is the best time to visit Winslow?
If you want the joy of a fun-filled trip in peak season, visit Winslow during May, June and August. If you'd prefer the peace of off-season, book a stay during quieter months, such as December, January and February.
When is the cheapest time to stay in Winslow?
Based on historic data is usually the cheapest month to visit Winslow. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Winslow?
There are multiple hotels in Winslow that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winslow. We have plenty of kid-friendly hotels in Winslow to choose from on Travelocity!
Why book a hotel in Winslow through Travelocity?
Because we have the top hotels in Winslow! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Winslow on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Winslow hotel reviews by fellow wanderers

Darlington Inn

Darlington Inn

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Our check in was easy n the receptionist was great to deal with. We had a pretty easy time finding parking for our truck n 20 ft trailer we were pulling. Our room was very clean and inviting. We will definitely stay again. "
A verified traveler stayed at Darlington Inn
Darlington Inn