Winslow Holiday Rentals

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Holiday Rentals in Winslow

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
Fridge, microwave, oven, stovetop
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
9.8 out of 10, Exceptional, (153)
"Our stay was nothing short of amazing. The entire stay was absolutely what we all needed. We felt right at home with how beautifully the place is maintained and the love that is put into making this space feel like a safe haven."
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
3 Bedroom, 3.5 bath house in The Galena Territory.
Property grounds
3 Bedroom, 3.5 bath house in The Galena Territory.
9.8 out of 10, Exceptional, (159)
"Loved this place. Close enough to downtown…close to wineries and golf. Will return…."
3 Bedroom, 3.5 bath house in The Galena Territory.
Beautiful Lakehouse with private dock on Apple Canyon Lake!
Property grounds
Beautiful Lakehouse with private dock on Apple Canyon Lake!
9.8 out of 10, Exceptional, (88)
"The house was nice and clean. The bulletin board had all the information needed for our trip. Alex was a great resource for any questions/concerns we had. Overall had a wonderful stay at the property."
The price is AU$865
per night
8 July - 9 July
Beautiful Lakehouse with private dock on Apple Canyon Lake!
Beautiful Apple Canyon Lake Log Cabin in the Woods
Pool
Beautiful Apple Canyon Lake Log Cabin in the Woods
9.8 out of 10, Exceptional, (155)
"Great place! tons of blankets! tons of cookware, all the basics, everything went so smooth. comfortable place. cool hiking and fishing all around. cant wait to come back!"
Beautiful Apple Canyon Lake Log Cabin in the Woods
Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table
Exterior
Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table
10.0 out of 10, Exceptional, (279)
"We haven't been to Galena since 2019 and we were eager to visit a wonderful area of Illinois. We weren't disappointed with our visit starting off with Ginger's wonderful, secluded home. The property was as described and worthy of the 200+ ten-star reviews. Having 3 bedrooms, each with their separate bathrooms was perfect for the 3 couples that comprised our party. Firepit, BBQ grill and all the appliances were in working condition and enjoyed by all! Didn't have the opportunity to use the hot...
Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Exterior
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
10.0 out of 10, Exceptional, (117)
"Enjoy the peace and quiet of this beautiful house up on the hill."
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Apple Canyon Lake Home, Life At The Lake
Pool
Apple Canyon Lake Home, Life At The Lake
10.0 out of 10, Exceptional, (58)
"The homeowners were very accommodating and communicated immediately. Very enjoyable, we are very lucky to have hosts that open their homes to us. Thank You."
Apple Canyon Lake Home, Life At The Lake
Beautiful Lake house with own beach, and walking trails
Interior
Beautiful Lake house with own beach, and walking trails
9.8 out of 10, Exceptional, (20)
"We stayed here with 4 adults and 6 kids. It was a perfect size. The view of the lake is amazing! The covered deck allowed us to enjoy an awesome thunderstorm viewing without getting wet. The kids loved fishing off the dock, playing in the sand, & playing pool. We made lots of great memories during our stay!"
Beautiful Lake house with own beach, and walking trails
Quiet Farmhouse-Style Cabin w/ Front Porch!
Property grounds
Quiet Farmhouse-Style Cabin w/ Front Porch!
10.0 out of 10, Exceptional, (38)
"Perfect peaceful retreat to serve as base camp to explore Wisconsin’s driftless region. My wife and I really appreciated the little touches that make this cabin special. We would definitely stay here again."
Quiet Farmhouse-Style Cabin w/ Front Porch!
Spacious Apple Canyon Lake home - just minutes from Galena, Illinois
Pool
Spacious Apple Canyon Lake home - just minutes from Galena, Illinois
10.0 out of 10, Exceptional, (5)
"This this an incredible home on the lake! The home was gorgeous, the views were unbelievable...we couldn't ask for anything more. If I needed to ask the owner a question, he was very prompt with his response. No doubt, would book again! Thank you for letting us stay here :)"
Spacious Apple Canyon Lake home - just minutes from Galena, Illinois
Cozy home with beautiful LAKE VIEW!
Pool
Cozy home with beautiful LAKE VIEW!
Cozy home with beautiful LAKE VIEW!
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
Fridge, microwave, oven, stovetop
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
9.6 out of 10, Exceptional, (62)
"We enjoyed our stay at the log cabin. The accommodations were as advertised. The owners were very responsive to questions. The exterior of the property needed its spring cleanup and then it would have looked like the photos. The screen was torn out of the back entry to the porch. There was hair in the main floor sheets. We really liked sitting on the porch and even got a visit from a fox on our last morning!"
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
Comfortable ,and beautifully furnished,with antiques,and comfy furniture .
Fridge, microwave, oven, stovetop
Comfortable ,and beautifully furnished,with antiques,and comfy furniture .
10.0 out of 10, Exceptional, (68)
"Sandy our host was very friendly, polite and on the ball. Breakfast was excellent with a nice variety plus our breakfast times varied with the activities we had planned and Sandy was very accommodating. House was clean and well kept. Beds were comfortable"
Comfortable ,and beautifully furnished,with antiques,and comfy furniture .
MJ's Penthouse ( a piece of paradise on Monroe's historic square)<br>
Smart TV
MJ's Penthouse ( a piece of paradise on Monroe's historic square)<br>
10.0 out of 10, Exceptional, (69)
"It was beautiful and was a perfect location."
The price is AU$397
per night
25 June - 26 June
MJ's Penthouse ( a piece of paradise on Monroe's historic square)<br>
amazing house, with10 mile views, on 300 acres near Galena Territory. Hot tub.
Exterior
amazing house, with10 mile views, on 300 acres near Galena Territory. Hot tub.
9.8 out of 10, Exceptional, (36)
"This property has absolutely gorgeous views. We were there in late March..not the prettiest time of year in Illinois..but it was still stunning. I don't think the pictures and listing (while very nice) do it justice..its even prettier in person. The house is a unique 70s era ocatagon house, with comfortable furnishings and an open kitchen/living area on the main floor which is ideal when you are on vacation and want to hang out with your friends and family but still have to cook. The ranch hand,...
amazing house, with10 mile views, on 300 acres near Galena Territory. Hot tub.
Relaxing Retreat with Hot Tub and Fire Pit
Exterior
Relaxing Retreat with Hot Tub and Fire Pit
10.0 out of 10, Exceptional, (13)
"My co-workers and I took a trip to relax. It was a beautiful place to stay and had excellent communication with Andrew. We would absolutely book again. :)"
Relaxing Retreat with Hot Tub and Fire Pit
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
Property grounds
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
10.0 out of 10, Exceptional, (3)
"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."
The price is AU$8,908
per night
25 June - 26 June
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
View from property
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
9.6 out of 10, Exceptional, (57)
"Great property for a family Thanksgiving gathering Large kitchen and plenty of room for all to gather and enjoy time together The kids loved the trails and animals and beautiful views Loved the hot tub!"
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
Ridgeview suites, near Galena Territory, 300 acre ranch. HotTub, Golf, Animals
Property grounds
Ridgeview suites, near Galena Territory, 300 acre ranch. HotTub, Golf, Animals
Ridgeview suites, near Galena Territory, 300 acre ranch. HotTub, Golf, Animals
Destination Driftless- A Trailside Retreat
Exterior
Destination Driftless- A Trailside Retreat
9.4 out of 10, Exceptional, (21)
"Wondering location not far from the ATV trails loved the old farm house feel and decor will definitely stay again hopefully longer next time !!"
Destination Driftless- A Trailside Retreat
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See all available properties in Winslow
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.

Other types of properties in Winslow you may be interested in

Super 8 by Wyndham Monroe WI
Exterior
Super 8 by Wyndham Monroe WI
2.0 star property
9.0 out of 10, Wonderful, (613)
"I was quite pleased "
The price is AU$112
per night
7 July - 8 July
Super 8 by Wyndham Monroe WI
Country Inn & Suites by Radisson, Stockton, IL
Lobby
Country Inn & Suites by Radisson, Stockton, IL
2.5 star property
8.6 out of 10, Excellent, (485)
"Pool hours not very accomadationg"
The price is AU$117
per night
8 July - 9 July
Country Inn & Suites by Radisson, Stockton, IL
Country Inn & Suites by Radisson, Freeport, IL
Lobby
Country Inn & Suites by Radisson, Freeport, IL
2.5 star property
9.0 out of 10, Wonderful, (697)
"The property is located in northwest Illinois a very scenic area to the west towards the Mississippi River. The property is an older but well maintained property. The room is nice and comfortable. "
The price is AU$186
per night
18 June - 19 June
Country Inn & Suites by Radisson, Freeport, IL
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.

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$397 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?

Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table: This holiday home rental outside of Winslow is located near skiing, and has a fireplace, a balcony 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 garden, a selection of games and 1 hot tub 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 Roth Kase Cheese Factory, or get out into nature at a spot like Lake Le Aqua Na State Park. Historic Cheesemaking Center and Minhas Craft Brewery 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.

Recent reviews of Winslow properties
Expedia verified reviews

Baymont by Wyndham Freeport

Baymont by Wyndham Freeport

5/5 Excellent
"I liked how helpful and caring LaMay was. I have a hard time walking and use a motorized wheelchair and I went outside to smoke a cigarette and I was coming in and she came out and helped by holding the doors open so I could get in easy. "
A verified traveller stayed at Baymont by Wyndham Freeport
Posted 4 days ago
Baymont by Wyndham Freeport