Winslow Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Winslow vacation 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!

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.
The price is ￥11,389
￥45,488 total
includes taxes & fees
Jan 11 - Jan 12
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
Exterior
Hamilton Goebel House 816 E Louisa St Darlington Wi

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, (48)
"It was a great place to stay!!! The owners were great to deal with!!! Will be coming back"
United States
Michelle M.
Hamilton Goebel House 816 E Louisa St Darlington Wi
Interior
Peace & Simplicity in a Little Red Cabin on the Farm

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, (13)
"Quiet, clean and absolutely lovely cabin! "
United States
Holley B.
The price is ￥21,938
￥26,572 total
includes taxes & fees
Jan 20 - Jan 21
Peace & Simplicity in a Little Red Cabin on the Farm
Living area
The Minor House - A Cozy Stay in Shullsburg

The Minor House - A Cozy Stay in Shullsburg

The Minor House - A Cozy Stay in Shullsburg
2.0 star property
Shullsburg
The price is ￥14,416
￥26,947 total
includes taxes & fees
Jan 10 - Jan 11
The Minor House - A Cozy Stay in Shullsburg
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

MJ's Penthouse ,a piece of paradise on Monroe's historic square
Monroe
10.0 out of 10, Exceptional, (102)
"Such a fun place to stay! We loved it!"
United States
Karen J.
The price is ￥30,557
￥42,211 total
includes taxes & fees
Jan 12 - Jan 13
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Interior
Lookout Loft over the Monroe Square

Lookout Loft over the Monroe Square

Lookout Loft over the Monroe Square
2.0 star property
Monroe
The price is ￥15,182
￥33,290 total
includes taxes & fees
Jan 11 - Jan 12
Lookout Loft over the Monroe 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.

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.
The price is ￥548,450
￥990,944 total
includes taxes & fees
Jan 26 - Jan 27
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
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

Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
Elizabeth
9.6 out of 10, Exceptional, (78)
"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 ￥61,976
￥148,158 total
includes taxes & fees
Jan 27 - Jan 28
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

10/10 Excellent
"Safe, clean & convenient."
Laura 1-night trip
Posted 6 days ago
Country Inn & Suites by Radisson, Freeport, IL

Find out more about Winslow

Search for holiday rentals in Winslow on Expedia! You can easily find your home rentals, villas, holiday apartments in Winslow using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winslow!

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?

Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table: Visitors like this Winslow vacation home rental. It is located near skiing and has a fireplace, a balcony, and a barbecue grill 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 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.

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 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.