Winslow Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Winslow

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)
"The owners are easy to work with. The property is incredible, and the setting in the river is perfect. Enjoyed coffee on the porch overlooking the river every morning and the kayaking was a lot of fun. Would love to come back sometime. "
United States
kent h.
The price is AU$1,042
includes taxes & fees
12 Nov - 13 Nov
Avail. Christmas! Lake Cabin w/King, Sauna
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)
"Wonderful hosts, a neat and clean little space, and surrounded by beautiful old, trees. This is a peaceful oasis (and it has a couple of breweries within a short drive)!"
United States
Todd H.
The price is AU$263
includes taxes & fees
17 Nov - 18 Nov
Peace & Simplicity in a Little Red Cabin on the Farm
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)
"This little A Frame house made for a wonderful, cozy stay for my husband and I on our second honeymoon! The online pictures didn't do this classy house justice! It was very clean, in a quiet neighborhood, good size lot, had everything we could need. Hope to stay here again!"
United States
Brian B.
The price is AU$381
includes taxes & fees
19 Nov - 20 Nov
🏠 Charming A-Frame w/ Mid-Century Vibe 1 Bed/1 Bath near Elizabeth, Illinois🌲
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)
"Clean and comfy"
United States
Nick N.
The price is AU$440
includes taxes & fees
23 Nov - 24 Nov
Hamilton Goebel House 816 E Louisa St Darlington Wi
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)
"Super clean and cute house that was great walking distance to everything! The hosts were great and easy to work with as well."
United States
Emma K.
The price is AU$474
includes taxes & fees
11 Dec - 12 Dec
Beautiful two story, downtown home, one block from the Square,
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, (101)
"Absolutely perfect! The best place in Monroe. Accommodating - from dinnerware to a pack-and-play - for every need! Five stars."
United States
Benjamin R.
The price is AU$425
includes taxes & fees
12 Nov - 13 Nov
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Living area
Lookout Loft over the Monroe Square

Lookout Loft over the Monroe Square

2.0 star property
Monroe
The price is AU$334
includes taxes & fees
2 Dec - 3 Dec
Lookout Loft over the Monroe Square
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.
The price is AU$9,884
includes taxes & fees
18 Nov - 19 Nov
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
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)
"My family of 24 people (age ranges 1-70) stayed for one week at this wonderful rural property with pastoral views from an expansive deck. The evenings were serenely quiet and the days were filled with activities. We enjoyed petting Lucas the llama and the horses/donkey as well as viewing the peacocks. The equisitely historic town of Galena is a short drive away with plenty of shopping, eateries and tours. We biked along the Galena biking trail about 7 miles one way to Chestnut Mountain from...
United States
Thomas S.
The price is AU$4,172
includes taxes & fees
12 Nov - 13 Nov
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

Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI

10/10 Excellent
"Room was spotless. Staff was friendly. Very quiet night! Good coffee!"
Kathryn 1-night trip
Posted 3 days ago
Super 8 by Wyndham Monroe WI

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 favourite 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 depend 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 AU$263 per night. Entering your travel dates in the search wizard might find you 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?

MJ's Penthouse ,a piece of paradise on Monroe's historic square: This holiday home rental outside of Winslow is located in the city centre, 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 Cadiz Springs State Recreation Area 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.