Default HTG hotel image

Winslow Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Winslow vacation rentals

A wooden cabin with a porch, a picnic table, and a fire pit.

1. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (37 reviews)
"Very happy with our stay here. The cabin was clean, the beds were comfortable, and the owners were very easy to communicate with. We would definitely stay here again."
United States
Cyndi L.
The price is ￥19,721
￥38,344 total
includes taxes & fees
Nov 1 - Nov 2
Yellow Banks Log Cabin With Waterfront Views
A room with a white door, a wooden floor, and a wall with decorative butterfly and flower art.

2. Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Huntingburg
9.8 out of 10, Exceptional, (30 reviews)
"Me and my family stayed while visiting holiday world and we highly recommend. Prices was affordable and the host was great."
United States
James B.
The price is ￥15,619
￥30,746 total
includes taxes & fees
Oct 30 - Oct 31
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
A cozy cabin interior with a sofa, dining table, and chairs.

3. Yellow Banks Log Cabin with Lake Views

Yellow Banks Log Cabin with Lake Views
Dale
8.8 out of 10, Excellent, (29 reviews)
"A nice little cabin for our trip to holiday world."
United States
Brandon R.
The price is ￥27,610
￥48,593 total
includes taxes & fees
Nov 1 - Nov 2
Yellow Banks Log Cabin with Lake Views
A wooden gazebo with a gravel path leading to a pond, surrounded by trees and a grassy area.

4. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (25 reviews)
"Great location,very clean and cozy!"
United States
Briley E.
The price is ￥23,666
￥43,469 total
includes taxes & fees
Nov 1 - Nov 2
Yellow Banks Log Cabin With Waterfront Views
A rustic wooden building with a covered porch and a picnic table.

5. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.8 out of 10, Exceptional, (8 reviews)
"This was a quiet, clean, and convenient little cabin close to Holiday World which is what we stayed for. "
United States
Ashley J.
The price is ￥24,454
￥44,529 total
includes taxes & fees
Nov 1 - Nov 2
Yellow Banks Log Cabin With Waterfront Views
A living room with a sofa, coffee table, and TV. There is a kitchen area with cabinets and a refrigerator. A ceiling fan is visible, and a welcome sign is on the wall.

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

Cozy East Side Condo in Washington close to City Park and Hospital
Washington
10.0 out of 10, Exceptional, (37 reviews)
"Great space for my family of five. The three bedrooms and two full bathrooms plus laundry made our stay much easier."
United States
Dee A.
Cozy East Side Condo in Washington close to City Park and Hospital
A wooden interior with a television, wooden cabinets, and a plant.

7. Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (74 reviews)
"Nice quaint place to stay. 10/10 would recommend and stay if in the area again"
United States
Chasity D.
The price is ￥22,561
￥28,979 total
includes taxes & fees
Nov 3 - Nov 4
Guest House with acreage to explore.
A compact kitchen with wooden cabinets, a stainless steel refrigerator, an oven, a microwave, a sink, and a kettle. There is a dining table with chairs.

8. 5 Miles from Holiday World sleeps 11+ —Family Escape

5 Miles from Holiday World sleeps 11+ —Family Escape
Dale
9.8 out of 10, Exceptional, (35 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
The price is ￥39,048
￥65,116 total
includes taxes & fees
Nov 1 - Nov 2
5 Miles from Holiday World sleeps 11+ —Family Escape
A single-story house with a gabled roof, white shutters, and a front porch.

9. 3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World

3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
Ferdinand
10.0 out of 10, Exceptional, (4 reviews)
"The property was conveniently located within all of our planned attractions."
United States
Lavar B.
The price is ￥23,666
￥39,935 total
includes taxes & fees
Nov 2 - Nov 3
3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
A wooden cabin with a covered porch, a picnic table, and a view of a lake.

10. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.0 out of 10, Wonderful, (18 reviews)
"Excellent cabins! We had so much fun!!!"
United States
Leslie H.
The price is ￥23,666
￥43,469 total
includes taxes & fees
Nov 1 - Nov 2
Yellow Banks Log Cabin With Waterfront Views
A bedroom with a wooden wall panel, a bed with white bedding, and a small shelf with decorative items.

11. Princeton Suite 7 - QUEEN 1BD/1BA Apt

Princeton Suite 7 - QUEEN 1BD/1BA Apt
Princeton
The price is ￥10,951
￥25,518 total
includes taxes & fees
Nov 1 - Nov 2
Princeton Suite 7 - QUEEN 1BD/1BA Apt
A spacious living room with a fireplace, a large window, and a high ceiling with exposed beams.

12. Family Friendly Lakehouse with great views!

Family Friendly Lakehouse with great views!
Jasper
10.0 out of 10, Exceptional, (14 reviews)
"Very beautiful and comfortable house for our stay"
United States
James S.
The price is ￥50,802
￥64,143 total
includes taxes & fees
Nov 2 - Nov 3
Family Friendly Lakehouse with great views!
A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

13. The Cowboys Slumber' 2 Mi to Lincoln State Park

The Cowboys Slumber' 2 Mi to Lincoln State Park
3.0 star property
Gentryville
The Cowboys Slumber' 2 Mi to Lincoln State Park
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.
View all properties
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

Clarion Pointe Jasper

Clarion Pointe Jasper

10/10 Excellent
"Super friendly and helpful staff, easy location, I liked the coffee choices."
Denise 1-night trip
Posted 2 days ago
Clarion Pointe Jasper

Find out more about Winslow

Search for holiday rentals in Winslow on Expedia! You can easily find your home rentals, villas, holiday apartments in Winslow using one of the methods below:

  • View our selection of featured holiday rentals in Winslow
  • Use the map to find apartments and other holiday homes in the Winslow neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winslow while they last

Look no further and take a look at our great range of rental properties in Winslow!

Frequently asked questions

Are there vacation rentals in Winslow?

Yes, we give you a choice of vacation rentals close to top attractions in Winslow, or you can choose a more remote option if you want a relaxing place to stay.

What's the top vacation rental that Winslow has to offer?

Large Home Sleeps 24 in Santa Claus 5 Mins from Holiday World with a Game Room: This vacation home rental outside of Winslow offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Winslow?

While exploring the area, visit the sights like Oakland City University, Jasper City Mill, and Sultan's Run Golf Course. Dubois County Museum and St Joseph's Church are a couple of places you'll find in the larger area.

What are vacation rentals like in Winslow?

Vacation rentals are private accommodations you can stay in for several days or longer in Winslow. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a family trip.