Winslow Vacation Rentals

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Vacation 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, 154 reviews
"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 reviews
"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 reviews
"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 ￥55,199
￥89,737 total
includes taxes & fees
Jul 8 - Jul 9
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 reviews
"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, 281 reviews
"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
Exterior
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
10.0 out of 10, Exceptional, 117 reviews
"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
Pool
Apple Canyon Lake Home, Life At The Lake
10.0 out of 10, Exceptional, 58 reviews
"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!
Property grounds
Quiet Farmhouse-Style Cabin w/ Front Porch!
10.0 out of 10, Exceptional, 39 reviews
"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 reviews
"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, 63 reviews
"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 .
Fridge, microwave, oven, stovetop
Comfortable ,and beautifully furnished,with antiques,and comfy furniture .
10.0 out of 10, Exceptional, 69 reviews
"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>
Smart TV
MJ's Penthouse ( a piece of paradise on Monroe's historic square)<br>
10.0 out of 10, Exceptional, 69 reviews
"It was beautiful and was a perfect location."
The price is ￥30,753
￥41,274 total
includes taxes & fees
Jul 1 - Jul 2
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 reviews
"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 reviews
"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 reviews
"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 ￥551,985
￥918,818 total
includes taxes & fees
Jul 8 - Jul 9
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 reviews
"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
TV
Destination Driftless- A Trailside Retreat
9.4 out of 10, Exceptional, 21 reviews
"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,
Fridge, oven, stovetop, dishwasher
Beautiful downtown home, one block from the Square,
10.0 out of 10, Exceptional, 19 reviews
"This house was so cute! Modern decor and amenities with beautifully restored original hardwood floors. We would definitely stay here again! 😁"
The price is ￥40,728
￥65,514 total
includes taxes & fees
Jun 24 - Jun 25
Beautiful downtown home, one block from the Square,
Don't see what you're looking for?
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, 618 reviews
"My husband and I were very impressed with this Super 8 motel. The staff was very friendly. The room was super clean and spacious. We sat in the hot tub and swam in the pool. Both clean and appropriate temperature. There is an outdoor patio area off the pool area that is super cute and even has a BBQ grill. The breakfast was good, although my only complaint is that the hard boiled eggs weren't peeled and it was hard to peel them. BUT, I LOVED the warm cinnamon rolls! And I liked that they had a...
The price is ￥10,992
￥12,036 total
includes taxes & fees
Jul 8 - Jul 9
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, 489 reviews
"Room was clean. Pool was available and clean. Did have a small breakfast buffet. Was quiet when sleeping during the night."
The price is ￥11,054
￥12,270 total
includes taxes & fees
Jul 8 - Jul 9
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, 705 reviews
"All was great "
The price is ￥17,641
￥19,581 total
includes taxes & fees
Jul 1 - Jul 2
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.

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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?

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 spa 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 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 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.

Recent reviews of Winslow properties
Expedia verified reviews

Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI

5/5 Excellent
"My husband and I were very impressed with this Super 8 motel. The staff was very friendly. The room was super clean and spacious. We sat in the hot tub and swam in the pool. Both clean and appropriate temperature. There is an outdoor patio area off the pool area that is super cute and even has a BBQ grill. The breakfast was good, although my only complaint is that the hard boiled eggs weren't peeled and it was hard to peel them. BUT, I LOVED the warm cinnamon rolls! And I liked that they had a separate table with gluten free foods away from the other food (ex: eggs, yogurt, fruit cup, apples). We would stay there again if we are back in that area."
A verified traveler stayed at Super 8 by Wyndham Monroe WI
Posted 1 day ago
Super 8 by Wyndham Monroe WI