Winslow Holiday Rentals

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Holiday Rentals in Winslow

Guest House with acreage to explore.

9.6 out of 10, Exceptional, (46)
"Place was as described and perfect for us. Clean, comfortable and host was great with communication. Between the two of us we caught over 30 fish in the pond. Very fun. Thank you for a great stay "
The price is AU$253
includes taxes & fees
30 Nov - 1 Dec
Guest House with acreage to explore.

Yellow Banks Log Cabin with Lake Views

9.2 out of 10, Wonderful, (11)
"Nice secluded area, very tranquil setting "
The price is AU$428
includes taxes & fees
1 Dec - 2 Dec
Yellow Banks Log Cabin with Lake Views

Yellow Banks Log Cabin With Waterfront Views

9.6 out of 10, Exceptional, (11)
"The cabin was a nice visit and housed our family. There is a fire pit and a little pond that has some bluegill fish in it. The upstairs can get warm but had to set the living room fan to push the cold air up."
The price is AU$378
includes taxes & fees
1 Dec - 2 Dec
Yellow Banks Log Cabin With Waterfront Views

Spacious 1450 sf 2 BR Private Suite w/Dog Fe

10.0 out of 10, Exceptional, (8)
"We stayed overnight after going to Holiday World. The listing was accurate and the accommodations were clean and ready. Very enjoyable stay!"
The price is AU$330
includes taxes & fees
1 Dec - 2 Dec
Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Yellow Banks Log Cabin With Waterfront Views

10.0 out of 10, Exceptional, (6)
"This place was great, and peaceful. I'll definitely be staying here anytime my family visits holiday world. Almost spent our second day just at the cabin. So relaxing."
The price is AU$378
includes taxes & fees
1 Dec - 2 Dec
Yellow Banks Log Cabin With Waterfront Views

Charming 2-bedroom lake house in Dale

The price is AU$343
includes taxes & fees
2 Dec - 3 Dec
Charming 2-bedroom lake house in Dale

Yellow Banks Log Cabin With Waterfront Views

9.8 out of 10, Exceptional, (8)
"The location was perfect for our trip to Holiday World. The surrounding property is beautiful and and was perfect for a bonfire. We had lots of fun embracing the aspects of cabin living. Enough space for 5 college friends :)"
The price is AU$378
includes taxes & fees
1 Dec - 2 Dec
Yellow Banks Log Cabin With Waterfront Views

Enchanting Montgomery Escape w/ Private Hot Tub!

10.0 out of 10, Exceptional, (5)
"the property provided everything we asked of it. great memories were made."
Enchanting Montgomery Escape w/ Private Hot Tub!

The Family Oasis just 6 miles from Holiday World

9.2 out of 10, Wonderful, (33)
"The place was amazing. Very nice place to stay for the weekend "
The Family Oasis just 6 miles from Holiday World

Cozy East Side Condo in Washington close to City Park and Hospital

10.0 out of 10, Exceptional, (4)
"We enjoyed the condo. Plenty of room & very nice. "
The price is AU$533
includes taxes & fees
1 Dec - 2 Dec
Cozy East Side Condo in Washington close to City Park and Hospital

Another Oasis just 6 miles from Holiday World

8.8 out of 10, Excellent, (10)
"This house was amazing! The house was way bigger then we could of imagined. My whole family came and everyone had their own space. The bedrooms and closets are huge. The best part was the outside area. The host was gracious and quick to help with any issue. We will definitely be back. "
Another Oasis just 6 miles from Holiday World

X Marks the Spot(Blue)1.5 miles from Holiday World

9.8 out of 10, Exceptional, (8)
"We stayed here to spend two full days at Holiday World with our families. There were 5 adults and 4 kids. There were plenty of kitchen items for cooking. Excellent space for that post-park resting to be up and ready for the next day! Will definitely stay again! "
X Marks the Spot(Blue)1.5 miles from Holiday World

Truelove Chalet- A Relaxed, Rustic, Glam Cabin!

9.6 out of 10, Exceptional, (4)
"I would have given this 5 stars but the ants and gnats were bothersome, to where we left a day early. The cabin does have WiFi via starlink and it worked flawlessly. I would stay here again as it was quiet and peaceful."
Truelove Chalet- A Relaxed, Rustic, Glam Cabin!

THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8, Lg Drive, WiFi, Tankless Water Htr

2.0 star property
10.0 out of 10, Exceptional, (1)
"“The Getaway” was a good location to travel to other areas & see different things. The home was well stocked with everything you would need. Aubrey answered all questions and responded quickly. She even gave us some nearby things to do. "
The price is AU$425
includes taxes & fees
4 Dec - 5 Dec
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8, Lg Drive, WiFi, Tankless Water Htr

Quaint studio loft apartment on Eastside

10.0 out of 10, Exceptional, (1)
"I had a nice, convenient 10-days stay with much privacy. Matthew the host was friendly and helpfull and easy to be reached by messages."
Quaint studio loft apartment on Eastside

X Marks the Spot(Yellow)1.5 mi. from Holiday World

9.8 out of 10, Exceptional, (11)
"Had everything we needed. Especially enjoyed the front porch and fire pit. Nice big yard for grandkids to play when not at the park. Great spot! Thanks!"
X Marks the Spot(Yellow)1.5 mi. from Holiday World

Yellow Banks Log Cabin With Waterfront Views

9.8 out of 10, Exceptional, (8)
"It was a very nice cabin. It could have been a little cleaner. All in all it was great. "
The price is AU$378
includes taxes & fees
1 Dec - 2 Dec
Yellow Banks Log Cabin With Waterfront Views

Chestnut Street Retreat

10.0 out of 10, Exceptional, (33)
"My family and I came down for Holiday World. Perfect homey place to relax before and after! Would totally return!"
Chestnut Street Retreat

Historic home by Dogwood Lake/Glendale

10.0 out of 10, Exceptional, (1)
Historic home by Dogwood Lake/Glendale

X-Marks the Spot(Red) 1.5 miles from Holiday World

10.0 out of 10, Exceptional, (2)
"Overall, the house was a great stay to go to Holiday world. I would stay again if I went back."
X-Marks the Spot(Red) 1.5 miles from Holiday World
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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Other types of properties in Winslow you may be interested in

Baymont by Wyndham Washington

2.5 star property
8.0 out of 10, Very good, (565)
"This hotel has a very good breakfast!"
The price is AU$170
includes taxes & fees
30 Dec - 31 Dec
Baymont by Wyndham Washington

Hampton Inn Princeton

2.5 star property
9.2 out of 10, Wonderful, (427)
"Very clean and quiet. Great breakfast and coffee. Close to highway."
The price is AU$167
includes taxes & fees
13 Dec - 14 Dec
Hampton Inn Princeton

Baymont by Wyndham Evansville North/Haubstadt

2.5 star property
7.6 out of 10, Good, (917)
"Basic hotel. Nothing extraordinary. You get what you pay for. "
The price is AU$98
includes taxes & fees
15 Dec - 16 Dec
Baymont by Wyndham Evansville North/Haubstadt
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Spacious 1450 sf 2 BR Private Suite w/Dog Fe: This holiday home rental outside of Winslow offers a fireplace, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What can I see and do in Winslow?

While exploring the area, visit the sights like Oakland City University, St Joseph's Church and Jasper City Mill. Sultan's Run Golf Course and Alvin C. Ruxer Municipal Golf Course are a couple of places you'll find in the wider area.

What are holiday rentals like in Winslow?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winslow. Holiday rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a small group gathering.