Winslow Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Winslow

Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location

9.6 out of 10, Exceptional, (100)
"What a peaceful respite! Set in a lovely area, walking distance to the Apple Canyon Lake with a beach and restaurant, this was the perfect getaway for a family wedding weekend. The cabin is stunning and comfortable. Beautifully furnished, it had all of the amenities one could hope for in a vacation home."
Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake

9.8 out of 10, Exceptional, (207)
"Roomy and comfy cabin. Enjoyed our stay!"
Amazing Log Cabin with Beautiful Views at Apple Canyon Lake

Hamilton Goebel House 816 E Louisa St Darlington Wi

9.8 out of 10, Exceptional, (43)
"This was a wonderful property. The hosts were so accommodating and helpful. We had a great time."
The price is AU$348
includes taxes & fees
29 Sept - 30 Sept
Hamilton Goebel House 816 E Louisa St Darlington Wi

Discover Elizabeth charm, just a quick 27-min drive away from Mississippi River

10.0 out of 10, Exceptional, (100)
"Our hostess thought of all our needs. The delicious breakfast that she made each morning was like clockwork at our requested time. The home was cozy, comfortable, and fulfilled our needs."
Discover Elizabeth charm, just a quick 27-min drive away from Mississippi River

Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.

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."
The price is AU$9,671
includes taxes & fees
1 Oct - 2 Oct
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.

Peace & Simplicity in a Little Red Cabin on the Farm

10.0 out of 10, Exceptional, (8)
The price is AU$206
includes taxes & fees
30 Sept - 1 Oct
Peace & Simplicity in a Little Red Cabin on the Farm

White Oak Retreat SW WI easy access to ATV and Snowmobile Trails

10.0 out of 10, Exceptional, (22)
"awesome property and stay"
White Oak Retreat SW WI easy access to ATV and Snowmobile Trails

LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS

9.8 out of 10, Exceptional, (69)
"This was the perfect location for our family of 21 to gather for Thanksgiving. The ranch had so many animals and places to roam and all the kids had fun playing on the baseball field. Enough ovens for all of the Thanksgiving Turkey and sides to be eaten hot, and enough room for all to enjoy our time together. Great location near Galena!"
The price is AU$4,353
includes taxes & fees
26 Oct - 27 Oct
LUXURIOUS RANCH, 360 VIEWS, NEAR GALENA TER., 300 ACRES, TRAILS, PONDS, ANIMALS

Bungalow in the Burg - 1 block from downtown

10.0 out of 10, Exceptional, (29)
"Nice place, will stay again when in the area."
Bungalow in the Burg - 1 block from downtown

Beautiful two story, downtown home, one block from the Square,

10.0 out of 10, Exceptional, (33)
"Everything was very clean and welcoming. The decor was cute and cozy. Overall great stay."
The price is AU$489
includes taxes & fees
1 Oct - 2 Oct
Beautiful two story, downtown home, one block from the Square,

Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table

10.0 out of 10, Exceptional, (321)
"We had an amazing stay. The only downside was that we had so many plans we didn't get to enjoy the property more!"
Charming 3BR / 3BA With Hot Tub, Fireplace & Pool Table

Cozy King + Queen Suite | Near Golf, Lake & Marina

6.0 out of 10, (1)
"Room was very clean, nicely decorated, and spacious. The bathroom is very cramped with a tiny shower and it seems odd that the mini fridge and coffee m"
Cozy King + Queen Suite | Near Golf, Lake & Marina

MJ's Penthouse ,a piece of paradise on Monroe's historic square

10.0 out of 10, Exceptional, (96)
"Had a great stay for St Pats Parade!"
The price is AU$416
includes taxes & fees
12 Oct - 13 Oct
MJ's Penthouse ,a piece of paradise on Monroe's historic square

Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL

10.0 out of 10, Exceptional, (25)
"Lovely, comfortable and spacious, this house was close to so many places we wanted to go."
Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL

Relaxing Retreat with Hot Tub and Fire Pit

10.0 out of 10, Exceptional, (32)
"Lovely property, very comfortable and very well stocked with anything you might need! Loved the screened in porch! Would definitely recommend!"
Relaxing Retreat with Hot Tub and Fire Pit

New 5-bedroom house at Apple Canyon Lake. 30 minutes from downtown Galena!

10.0 out of 10, Exceptional, (10)
"We weren't there long or in the house much but the house was beautiful and very warming. Melany was very responsive and we had no issues whatsoever."
New 5-bedroom house at Apple Canyon Lake. 30 minutes from downtown Galena!

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

10.0 out of 10, Exceptional, (153)
"Great location to roam around the southern area of Wisconsin"
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

Spacious Apple Canyon Lake home - just minutes from Galena, Illinois

10.0 out of 10, Exceptional, (13)
"House was perfect, updated and close to everything. Owner was responsive and great to work with. Would definitely stay again."
Spacious Apple Canyon Lake home - just minutes from Galena, Illinois

The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.

9.0 out of 10, Wonderful, (4)
"We loved our stay. This property was just as described, on a quiet dead end road. There were lots of towels and GREAT pillows. This was our ATV trip and this property is just a few blocks away from the ATV trail. We enjoyed watching the cows as they watched us. We will stay again."
The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.

Cozy home with beautiful LAKE VIEW!

9.4 out of 10, Exceptional, (10)
"This house was Fantastic, we own a lot at the lake but it was great to beable to stay the whole weekend and have family come for a day to spend with us on the boat and at the pool to celebrate, a Birthday, Fathers Day, and an Anniversary"
Cozy home with beautiful LAKE VIEW!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winslow Hotel Reviews

Find out more about Winslow

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$206 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?

Hamilton Goebel House 816 E Louisa St Darlington Wi : This holiday home rental outside of Winslow has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.