Winslow Holiday Rentals from AU$205: Search Short-Term Rentals

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Holiday Rentals in Winslow

Stunning two-story home with a central entrance, flanked by windows, and a charming balcony above.

"We enjoyed our stay, peaceful, clean and everything we needed. "

Cozy cabin interior with a spacious kitchen, central island, and dishwasher. A high ceiling with exposed beams and large windows complete the space.

"We loved our stay! Great communication with Mia! We arrived early and she gave us the passes to the pool and beach so we could hangout there while the cabin was being cleaned. Great hosts! Loved the welcome basket with goodies because our kids were hungry. Such a great touch! Pictures are exactly what the home looks like. Thank You!"

Swimmers enjoy the rectangular pool surrounded by lounge chairs and windows offering views of the outdoors.

"Everything was perfect. Thank you! "

Enjoy cooking in this well-equipped kitchen with a stainless steel sink, microwave, and stove.

"Great place to stay and great atmosphere. Close to Galena and plenty to do. "

Golfers can enjoy a serene setting with access to golf equipment and a traditional clubhouse.

"The hosts are very responsive. The room is clean and decorated nicely. Overall, we would recommend."

includes taxes & fees

27 July - 28 July

Relax in a serene hot tub surrounded by lush greenery and a breathtaking valley view.

"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!"

Relax by the serene pool surrounded by a deck with lounge chairs and umbrellas, offering a view of the calm lake and distant trees.

"Great location and property. It rained during our visit, but there were plenty of games to keep us entertained."

includes taxes & fees

29 July - 30 July

Traditional interior with a white cabinet, glass table, and dining area.

"Perfect place to stay when visiting the Cheese trail, will definitely return to this property! "

Relax on the covered porch with two comfortable chairs and a ceiling fan overhead.

"Lovely, comfortable and spacious, this house was close to so many places we wanted to go."

Relax in a serene hot tub surrounded by lush greenery and a breathtaking view.

"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."

includes taxes & fees

5 Aug - 6 Aug

Escape to a serene cabin nestled among lush greenery, with a cozy porch and stairs leading to the entrance.

"Great location with nice vies"

Stroll through the serene garden, surrounded by vibrant flowers and a charming picket fence, leading to a rustic building.

"Great weekend with girls. Host was very attentive. Location was great, close to shopping and wineries."

Cozy cabin-style accommodation with a wooden staircase, storage cabinet, and a comfortable bed.

"Relaxing quiet and great host "

Cozy living room with a fireplace, wooden accent wall, and a white-framed window.

"Nice place, will stay again when in the area."

Escape to a secluded cabin surrounded by trees and shrubs, featuring a chimney, large windows, and a porch with a railing.

"This was the perfect place for a relaxing girls weekend!!"

Enjoy golfing at this picturesque golf club with a clubhouse, golf cart rentals, and beautifully maintained grounds.

"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"

includes taxes & fees

27 July - 28 July

Enjoy cooking in this kitchen with microwave and stainless steel refrigerator, surrounded by a stone wall.

"The owners were very helpful. The property on the inside was very clean. The yard was overgrown and needed attention."

includes taxes & fees

7 Aug - 8 Aug

Enjoy cooking in this kitchen with sleek cabinetry, a large island, and stainless steel appliances.

"This is a beautiful brand new house with tons of room! We were able to walk down to the lake from the back yard to Ice fish."

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Winslow Hotel Reviews

Baymont by Wyndham Freeport

10/10 Excellent

"Great"

Apple Canyon Lake Home, Life At The Lake

10/10 Excellent

"We our family enjoyed our stay. The house was perfect size for our family. We enjoyed the amenities of the community properties, our littles ones and adults loved the pool. Jim was a very responsive in communicating with us. We would consider another stay here. "

3 Bedroom, 3.5 bath house in The Galena Territory.

10/10 Excellent

"We loved this place for a girls weekend, especially the en suite bathrooms in all the bedrooms. The drive to downtown was easy and scenic. Wasn’t there long enough to take advantage of the members club and pool. We enjoyed the house and the area. "

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$205 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?

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe: This holiday home rental outside of Winslow is located in a rural location, 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. You can relax into your holiday with a garden and a selection of games.

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 Historic Cheesemaking Center 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.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Winslow Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Holiday Rentals in Winslow

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

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

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake

3 Bedroom, 3.5 bath house in The Galena Territory.

3 Bedroom, 3.5 bath house in The Galena Territory.

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

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

Spacious Suite w/ 2 King Beds | Near Trails, Lake & Golf

Spacious Suite w/ 2 King Beds | Near Trails, Lake & Golf

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

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

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

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

Apple Canyon Lake Home, Life At The Lake

Apple Canyon Lake Home, Life At The Lake

Peace & Simplicity in a Little Red Cabin on the Farm

Peace & Simplicity in a Little Red Cabin on the Farm

Destination Driftless- A Trailside Retreat

Destination Driftless- A Trailside Retreat

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

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

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

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

Relaxing Retreat with Hot Tub and Fire Pit

Relaxing Retreat with Hot Tub and Fire Pit

Historic Country Farmhouse for ANY Season!

Historic Country Farmhouse for ANY Season!

Cabin on 35-Acre Farm in Blanchardville w/ Trails!

Cabin on 35-Acre Farm in Blanchardville w/ Trails!

Bungalow in the Burg - 1 block from downtown

Bungalow in the Burg - 1 block from downtown

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

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

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

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

Hamilton Goebel House 816 E Louisa St Darlington Wi

Hamilton Goebel House 816 E Louisa St Darlington Wi

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

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

Top Winslow Hotel Reviews

Baymont by Wyndham Freeport

Find out more about Winslow

Find out more about Winslow

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Trending destinations on Expedia.com.au

Frequently asked questions