Winslow Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Winslow holiday rentals

Dining

The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!

The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
Pearl City
10.0 out of 10, Exceptional, (3 reviews)
"Out of half a dozen or so cabin rentals, this one is the absolute best. It's clean, uncluttered, quiet, and huge! Water was hot, heater worked really well (it was a very cold week) and the kitchen worked well. Beds were comfy too. I can't say enough good things about this place!"
United States
Andrew R.
The price is NZ$517
includes taxes & fees
29 Mar - 30 Mar
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
Living area

The Minor House - A Cozy Stay in Shullsburg

The Minor House - A Cozy Stay in Shullsburg
Shullsburg
The price is NZ$292
includes taxes & fees
27 Mar - 28 Mar
The Minor House - A Cozy Stay in Shullsburg
Exterior

🏠 Charming A-Frame w/ Mid-Century Vibe 1 Bed/1 Bath near Elizabeth, Illinois🌲

🏠 Charming A-Frame w/ Mid-Century Vibe 1 Bed/1 Bath near Elizabeth, Illinois🌲
Elizabeth
10.0 out of 10, Exceptional, (4 reviews)
"Our stay was great! The cabin was exactly as expected like postures and clean. And the location was nice with a 5 minute drive to grocery stores and shops, as well as a 25 minute drive to Galena. "
United States
Lexi S.
The price is NZ$433
includes taxes & fees
29 Mar - 30 Mar
🏠 Charming A-Frame w/ Mid-Century Vibe 1 Bed/1 Bath near Elizabeth, Illinois🌲
Interior

Lookout Loft over the Monroe Square

Lookout Loft over the Monroe Square
Monroe
10.0 out of 10, Exceptional, (1 review)
"Couldn’t have asked for a better spot to stay. Monroe and the surrounding area have a lot to do. Stay at this place only heightened our experience. We will definitely be back. "
United States
Eric S.
The price is NZ$420
includes taxes & fees
20 Apr - 21 Apr
Lookout Loft over the Monroe Square
Interior

Peace & Simplicity in a Little Red Cabin on the Farm

Peace & Simplicity in a Little Red Cabin on the Farm
Lena
10.0 out of 10, Exceptional, (14 reviews)
"Quiet, clean and absolutely lovely cabin! "
United States
Holley B.
The price is NZ$289
includes taxes & fees
1 Apr - 2 Apr
Peace & Simplicity in a Little Red Cabin on the Farm
Interior

MJ's Penthouse ,a piece of paradise on Monroe's historic square

MJ's Penthouse ,a piece of paradise on Monroe's historic square
Monroe
10.0 out of 10, Exceptional, (102 reviews)
"Lovely property, great location, quiet and comfortable. "
United States
T. K. D.
The price is NZ$463
includes taxes & fees
30 Mar - 31 Mar
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Exterior

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
10.0 out of 10, Exceptional, (4 reviews)
"We had 14 people stay for a business retreat. Each had their own bedroom and bathroom. We gathered in the great room for our meeting, experienced cooking together and a ‘family dinner’ around the big table. We hiked as our activity and enjoyed a bonfire too. We went into galena one evening for dinner - just a quick 20 minute drive. We enjoyed our short stay and would consider returning."
United States
Katie L.
The price is NZ$10,415
includes taxes & fees
6 Apr - 7 Apr
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
Interior

LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS

LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
Elizabeth
9.8 out of 10, Exceptional, (72 reviews)
"The house was clean, beautiful and very spacious, we really enjoyed our stay. Hopefully next time we can plan a longer stay to tour around more. Owner and caretaker are all very accomodating."
United States
Frances E.
The price is NZ$4,482
includes taxes & fees
6 Apr - 7 Apr
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
Interior

Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond

Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
Elizabeth
9.6 out of 10, Exceptional, (80 reviews)
"We enjoyed our stay very much. Our whole group of friends enjoyed the stay. Joe was very quick to respond with any questions we had. He was great to work with. "
United States
Julie G.
The price is NZ$1,694
includes taxes & fees
6 Apr - 7 Apr
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
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.
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Top Winslow Hotel Reviews

Country Inn & Suites by Radisson, Freeport, IL

Country Inn & Suites by Radisson, Freeport, IL

4/10 Poor
"The room had only sheers covering the window. No privacy at night. There was also a bright light shining up to show the building that made it impossible to have a dark room (even with a blanket drapes across it!). The walls are thin (I could hear the room next door snoring). The internet connection is open (no security) and poor. It worked for only a few hours of the afternoon of the whole me stay (no bad weather to blame it on, beautiful day). The TV remote wouldn't turn on the TV. The hot tub keys were weak and not very many of them. The staff was great!"
Bryan 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Freeport, IL

Find out more about Winslow

Everything you need to know about Winslow holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winslow holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winslow holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winslow holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winslow. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winslow holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winslow holiday rentals we have selected for you start as low as NZ$289 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winslow rentals

At Expedia, we put the best Winslow holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winslow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winslow holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winslow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Winslow?

Yes, there are holiday rentals close to the most popular sights in Winslow, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winslow has to offer?

Unwind at High Ridge: Hot Tub Nights, Arcade Lights & Fire Pit Fun!: This holiday home rental outside of Winslow is located in the mountains, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and an arcade/games room so that you can immerse yourself in your holiday.

What can I see and do in Winslow?

Explore the area and family-friendly sights such as Little Cubs Field, or get out into nature at a spot like Apple River Canyon State Park. Lake Le Aqua Na State Park and Stagecoach Golf Course are a couple of places you'll find in the wider area.

What are holiday rentals like in Winslow?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winslow. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.