Search Holiday Rentals in Winslow

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Top Holiday Rentals in Winslow

Fridge, microwave, oven, stovetop
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
9.8 out of 10, Exceptional, (151)
"Great place to stay, just outside of lots of little towns. We loved the covered porch and the spacious cabin! Would highly recommend."
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
Property grounds
3 Bedroom, 3.5 bath house in The Galena Territory.
9.8 out of 10, Exceptional, (158)
"We enjoyed our stay very much. House is great and at a great location. We spent a lot of time sitting out on a porch just looking out in the woods, chatting. There’s plenty of space to do your own thing or enjoy the company. House is clean and well stocked. It is also short drive from most Galena attractions. We will definitely go back."
3 Bedroom, 3.5 bath house in The Galena Territory.
Exterior
Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table
10.0 out of 10, Exceptional, (278)
"We had a perfect weekend for three friends from grade school to reconnect. The weather was perfect and the house was perfect. There were three bedrooms on three different floors, a deck to view nature, and a large kitchen table to eat, play games and laugh. The host was wonderful and sent suggestions ahead of time. Their home was well stocked and very comfortable. We had a picnic at Galena vineyards, shopped main street, ate at Galena brewery and did the Goat trek! We would love to come back...
Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Pool
Apple Canyon Lake Home, Life At The Lake
10.0 out of 10, Exceptional, (56)
"Everything as-advertised. Very comfortable location."
Apple Canyon Lake Home, Life At The Lake
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
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
Exterior
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
10.0 out of 10, Exceptional, (112)
"We stayed at the house for our 2 day visit to New Glarus and Taliesin. The house is very clean and it has a large backyard for games."
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Exterior
Relaxing Retreat with Hot Tub and Fire Pit
10.0 out of 10, Exceptional, (12)
"Overall great accommodation. All beds were comfortable and was a great environment for our cousins reunion. We had a couple small hiccups and the owners were swift in response and transparent in situations. We would definitely book again"
Relaxing Retreat with Hot Tub and Fire Pit
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
Property grounds
Beautiful Lakehouse with private dock on Apple Canyon Lake!
9.8 out of 10, Exceptional, (86)
"We are all property owners who wanted a rental house for a weekend of relaxing and ice fishing. We were able to access the area we wanted to fiah, right from the property. Worked great! Will book again!"
The price is £665
per night
22 Jun - 23 Jun
Beautiful Lakehouse with private dock on Apple Canyon Lake!
Indoor pool, outdoor pool
Enjoy Our Hideaway! Fire Pit, Hot Tub, Games, Woodburning Fireplace & MORE+
9.8 out of 10, Exceptional, (95)
"Had a great time! Perfect house for the 6 of us!"
Enjoy Our Hideaway! Fire Pit, Hot Tub, Games, Woodburning Fireplace & MORE+
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
Fridge, microwave, oven, stovetop
Comfortable ,and beautifully furnished,with antiques,and comfy furniture .
10.0 out of 10, Exceptional, (67)
"Sandy's location is excellent. Out of the crowded Galena area, but close enough for an easy drive over for the day (about 20 - 25min traffic based). Breakfast was delicious and different every morning - Sandy will work with your dietary restrictions - talk with her about it. The space was large - entire upstairs with it's own kitchen if you prefer to cook your other meals yourself. Deck is lovely with a great view - could hardly believe how many stars in the sky. We enjoyed a fire in the firepit...
Comfortable ,and beautifully furnished,with antiques,and comfy furniture .
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!
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 £4,730
per night
4 Jun - 5 Jun
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
Exterior
Historic Country Farmhouse for ANY Season!
10.0 out of 10, Exceptional, (34)
"Great place to stay. The host was very helpful and accommodating. The house and property are kept up extremely nice. A lot of neat history all around. I look forward to staying again."
Historic Country Farmhouse for ANY Season!
Pool
Cozy home with beautiful LAKE VIEW!
Cozy home with beautiful LAKE VIEW!
Property grounds
Ridgeview suites, near Galena Territory, 300 acre ranch. HotTub, Golf, Animals
Ridgeview suites, near Galena Territory, 300 acre ranch. HotTub, Golf, Animals
Exterior
Apple Canyon Lake, Game Room, Hot Tub
9.0 out of 10, Wonderful, (44)
"Love this house. It’s comfortable and clean feels like home."
Apple Canyon Lake, Game Room, Hot Tub
Smart TV
MJ's Penthouse ( a piece of paradise on Monroe's historic square)<br>
10.0 out of 10, Exceptional, (68)
"We had a fantastic time, property is well laid out for a variety of different types of visitors. Hosts were flexible and helpful. We greatly enjoyed our stay."
The price is £209
per night
30 May - 31 May
MJ's Penthouse ( a piece of paradise on Monroe's historic square)<br>
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

Exterior
Super 8 by Wyndham Monroe WI
2.0 star property
9.0 out of 10, Wonderful, (610)
"The room was on the smaller side but was clean, with a comfortable bed and recliner. The toilet/tub area was small and separate from the sink area in the room. The internet was fast also. The breakfast was mostly cold offerings along with biscuits and gravy. This was our first stay at a Super 8 and it was a good experience. I would stay here again."
The price is £58
per night
9 Jun - 10 Jun
Super 8 by Wyndham Monroe WI
Lobby
Country Inn & Suites by Radisson, Stockton, IL
2.5 star property
8.6 out of 10, Excellent, (483)
"Pool hours not very accomadationg"
The price is £60
per night
16 Jun - 17 Jun
Country Inn & Suites by Radisson, Stockton, IL
Lobby
Country Inn & Suites by Radisson, Freeport, IL
2.5 star property
9.0 out of 10, Wonderful, (693)
"We always stay here when coming for the Pec flea market. Great place to stay but the price the last few years has made this very expensive compared to other hotels in the area."
The price is £97
per night
5 Jun - 6 Jun
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, apart-hotels, 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 favorite 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 depends 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 £209 per night. Entering your travel dates in the search wizard you might find 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

Quiet Farmhouse-Style Cabin w/ Front Porch!

Quiet Farmhouse-Style Cabin w/ Front Porch!

5/5 Excellent
Peaceful Retreat
"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."
A verified traveller stayed at Quiet Farmhouse-Style Cabin w/ Front Porch!
Posted 3 days ago
Quiet Farmhouse-Style Cabin w/ Front Porch!