Winslow Holiday Rentals

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Holiday Rentals in Winslow

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
9.8 out of 10, Exceptional, (154)
"We did an early Father's Day trip. Only living 2 hours away this was a nice quick trip. We loved how rural it was and I especially enjoyed the rockers on the front porch 🙂"
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
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!
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 NZ$926
includes taxes & fees
8 July - 9 July
8 Jul - 9 Jul
Beautiful Lakehouse with private dock on Apple Canyon Lake!
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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
10.0 out of 10, Exceptional, (281)
"Cabin was so peaceful but the best part was the host and housekeeper who took the extra time to go back and look for an item my daughter had left behind!! Who does that? Just wonderful memories from this stay for sure!"
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
10.0 out of 10, Exceptional, (117)
"The home was clean and quiet and very comfortable. We spent time on both the upstairs and downstairs porches drinking coffee in the morning, a little wine in the evenings. The only scary thing is the driveway up for me. No problem for my husband, though! Great place!! Would stay here again!"
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
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
Quiet Farmhouse-Style Cabin w/ Front Porch!
10.0 out of 10, Exceptional, (39)
"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
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!
Cozy home with beautiful LAKE VIEW!
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
9.6 out of 10, Exceptional, (63)
"The Cabin was beautiful and the country side with its rolling hills the cattle the trees and wild life was all great! The cabin was very clean and the hosts were great people and very helpful when needed. I went there on a quick getaway for my wife and I and we loved it all! Wineries, restaurants in Galena stores all within miles and minutes. Worth every penny"
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location
Comfortable ,and beautifully furnished,with antiques,and comfy furniture .
10.0 out of 10, Exceptional, (69)
"Delicious breakfasts, beautiful balcony to sit and listen to the birds or enjoy looking at the stars, comfortable chairs lots of windows with pretty views - a perfect time. Very responsive and knowledgeable hostess. Would highly recommend."
Comfortable ,and beautifully furnished,with antiques,and comfy furniture .
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 NZ$426
includes taxes & fees
15 July - 16 July
15 Jul - 16 Jul
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.
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
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.
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 NZ$9,497
includes taxes & fees
8 July - 9 July
8 Jul - 9 Jul
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
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
Ridgeview suites, near Galena Territory, 300 acre ranch. HotTub, Golf, Animals
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
Beautiful downtown home, one block from the Square,
10.0 out of 10, Exceptional, (19)
"This house was so cute! Modern decor and amenities with beautifully restored original hardwood floors. We would definitely stay here again! 😁"
The price is NZ$618
includes taxes & fees
25 June - 26 June
25 Jun - 26 Jun
Beautiful downtown home, one block from the Square,
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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
2.0 star property
9.0 out of 10, Wonderful, (618)
"Staff was very friendly and informative on balloon event for that weekend"
The price is NZ$121
includes taxes & fees
7 July - 8 July
7 Jul - 8 Jul
Super 8 by Wyndham Monroe WI
Country Inn & Suites by Radisson, Stockton, IL
2.5 star property
8.6 out of 10, Excellent, (489)
"Room was clean. Pool was available and clean. Did have a small breakfast buffet. Was quiet when sleeping during the night."
The price is NZ$127
includes taxes & fees
8 July - 9 July
8 Jul - 9 Jul
Country Inn & Suites by Radisson, Stockton, IL
Country Inn & Suites by Radisson, Freeport, IL
2.5 star property
9.0 out of 10, Wonderful, (705)
"We had a great time staying here. We went for a family wedding and the stay made for a wonderful time. The beds were comfy and the rooms were clean. The people who work there do a super job of making you feel welcome."
The price is NZ$202
includes taxes & fees
2 July - 3 July
2 Jul - 3 Jul
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winslow holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winslow. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winslow. Seeing all the best attractions is bound to make you fall in love with Winslow. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winslow short-term rentals, that won’t be hard to do.

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 SplashLand Family Water Park, 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
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