Winslow Vacation Rentals

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In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Winslow

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

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

2.5 star property
Pearl City
10.0 out of 10, Exceptional, (3)
"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.
$277 nightly
The price is $306
Dec 17 - Dec 18
Total with taxes and fees
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
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, (2)
"Our stay was perfect. The cabin was clean and cozy and had everything we needed! Brian was super responsive as well. "
United States
Tammy F.
$218 nightly
The price is $241
Nov 20 - Nov 21
Total with taxes and fees
🏠 Charming A-Frame w/ Mid-Century Vibe 1 Bed/1 Bath near Elizabeth, Illinois🌲
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, (11)
"Quiet, clean and absolutely lovely cabin! "
United States
Holley B.
$160 nightly
The price is $170
Nov 29 - Nov 30
Total with taxes and fees
Peace & Simplicity in a Little Red Cabin on the Farm
Fridge, microwave, oven, stovetop
Hamilton Goebel House 816 E Louisa St Darlington Wi

Hamilton Goebel House 816 E Louisa St Darlington Wi

Darlington
9.8 out of 10, Exceptional, (47)
"Close to town. "
United States
Juanita W.
$260 nightly
The price is $285
Nov 23 - Nov 24
Total with taxes and fees
Hamilton Goebel House 816 E Louisa St Darlington Wi
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)
"My husband and I stayed here and were so happy we did this home was beautiful and really something special. I highly recommend the stay here! "
United States
Katie B.
$240 nightly
The price is $263
Nov 20 - Nov 21
Total with taxes and fees
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Fridge, microwave, oven, stovetop
Avail. Christmas! Lake Cabin w/King, Sauna

Avail. Christmas! Lake Cabin w/King, Sauna

Brodhead
10.0 out of 10, Exceptional, (5)
"This is a beautiful home and area with a lot of fun activities. Love kayaking, playing pool, and sitting on the deck with the lake view."
United States
Jenelle K.
$639 nightly
The price is $674
Nov 24 - Nov 25
Total with taxes and fees
Avail. Christmas! Lake Cabin w/King, Sauna
Outdoor spa tub
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)
"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.
$5,945 nightly
The price is $6,301
Nov 26 - Nov 27
Total with taxes and fees
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
Fridge, microwave, oven, stovetop
Beautiful two story, downtown home, one block from the Square,

Beautiful two story, downtown home, one block from the Square,

Monroe
10.0 out of 10, Exceptional, (35)
"Everything was very clean and welcoming. The decor was cute and cozy. Overall great stay."
United States
Jeff Z.
$272 nightly
The price is $297
Dec 2 - Dec 3
Total with taxes and fees
Beautiful two story, downtown home, one block from the Square,
Living area
Lookout Loft over the Monroe Square

Lookout Loft over the Monroe Square

2.0 star property
Monroe
$213 nightly
The price is $233
Dec 2 - Dec 3
Total with taxes and fees
Lookout Loft over the Monroe Square
Outdoor spa tub
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, (69)
"Great hosts and a ton to do. Could have spent 2 weeks here for our family reunion and could not have done everything!"
United States
Damian W.
$2,510 nightly
The price is $2,660
Dec 1 - Dec 2
Total with taxes and fees
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS
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

10/10 Excellent
"Great staff."
Dawn 1-night trip
Posted 5 days ago
Country Inn & Suites by Radisson, Freeport, IL

Find out more about Winslow

Everything you need to know about Winslow vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winslow vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winslow vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winslow in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $170 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winslow rentals

At Expedia, we put the best Winslow vacation 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 vacation.

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.

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Frequently asked questions

Are there vacation rentals in Winslow?

Yes, we have vacation rentals near popular local attractions in Winslow, or you can select a more secluded option if you want a relaxing place to stay.

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

MJ's Penthouse ,a piece of paradise on Monroe's historic square: Visitors like this Winslow vacation home rental. It is located in the city center and has a balcony, a selection of games, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Winslow?

Explore the area and family-friendly sights such as SplashLand Family Water Park, or get out into nature at a spot like Apple River Canyon State Park. Lake Le Aqua Na State Park and Historic Cheesemaking Center are a couple of places you'll find in the larger area.

What are vacation rentals like in Winslow?

Vacation rentals are privately owned properties you can stay in for short or long periods in Winslow. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.