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Winslow Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winslow holiday rentals

A cozy cabin interior with a sofa, dining table, and chairs.

1. 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 NZ$543
includes taxes & fees
4 Oct - 5 Oct
Yellow Banks Log Cabin with Lake Views
A wooden cabin with a covered porch, a picnic table, and a view of a lake.

2. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.0 out of 10, Wonderful, (17 reviews)
"Excellent cabins! We had so much fun!!!"
United States
Leslie H.
The price is NZ$483
includes taxes & fees
14 Oct - 15 Oct
Yellow Banks Log Cabin With Waterfront Views
A rustic wooden building with a covered porch and a picnic table.

3. 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 NZ$491
includes taxes & fees
11 Oct - 12 Oct
Yellow Banks Log Cabin With Waterfront 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, (24 reviews)
"Great location,very clean and cozy!"
United States
Briley E.
The price is NZ$485
includes taxes & fees
4 Oct - 5 Oct
Yellow Banks Log Cabin With Waterfront Views
A two-story house with a front porch, two chairs, and a stone pillar.

5. THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water

THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
Lynnville
9.8 out of 10, Exceptional, (16 reviews)
"Very attentive host. Good value. This house was perfect for our group's trip to Holiday World. We're looking at staying again in the future."
United States
Patricia G.
The price is NZ$515
includes taxes & fees
6 Oct - 7 Oct
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
A wooden interior with a television, wooden cabinets, and a plant.

6. Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (74 reviews)
"The place was great, quiet and peaceful! "
United States
brian k.
The price is NZ$325
includes taxes & fees
27 Oct - 28 Oct
Guest House with acreage to explore.
A room with a white door, a wooden floor, and a wall with decorative butterfly and flower art.

7. 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, (29 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 NZ$347
includes taxes & fees
4 Oct - 5 Oct
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
A wooden cabin with a porch, a picnic table, and a fire pit.

8. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (35 reviews)
"We had a great time and enjoyed our stay!"
United States
Anonymous traveller
The price is NZ$427
includes taxes & fees
4 Oct - 5 Oct
Yellow Banks Log Cabin With Waterfront Views
A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

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

The Cowboys Slumber' 2 Mi to Lincoln State Park
3.0 star property
Gentryville
The price is NZ$702
includes taxes & fees
13 Oct - 14 Oct
The Cowboys Slumber' 2 Mi to Lincoln State Park
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.

10. 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, (36 reviews)
"Great value"
United States
ERIC
Cozy East Side Condo in Washington close to City Park and Hospital
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.

11. 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, (34 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
The price is NZ$778
includes taxes & fees
4 Oct - 5 Oct
5 Miles from Holiday World sleeps 11+ —Family Escape
A room with a blue sofa, wooden tables, and chairs, a round wall clock, and a white ceiling.

12. Princeton Suite 6 - KING 2BR/2BA

Princeton Suite 6 - KING 2BR/2BA
Princeton
2.0 out of 10, (1 review)
The price is NZ$337
includes taxes & fees
4 Oct - 5 Oct
Princeton Suite 6 - KING 2BR/2BA
A spacious living room with a fireplace, a large window, and a high ceiling with exposed beams.

13. Family Friendly Lakehouse with great views!

Family Friendly Lakehouse with great views!
Jasper
10.0 out of 10, Exceptional, (13 reviews)
"Very beautiful and comfortable house for our stay"
United States
James S.
The price is NZ$778
includes taxes & fees
2 Nov - 3 Nov
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.

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

The Cowboys Slumber' 2 Mi to Lincoln State Park
Gentryville
10.0 out of 10, Exceptional, (1 review)
"We had an excellent stay! Place was nice and homey, well decorated and perfectly clean! Host was on top of making sure we had everything we needed. Would definitely recommend for anyone wanting to stay close to Holiday World or Lincoln State Park!"
United States
Jennifer C.
The price is NZ$718
includes taxes & fees
13 Oct - 14 Oct
The Cowboys Slumber' 2 Mi to Lincoln State Park
A single-story house with a gabled roof, white shutters, and a front porch.

15. 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 NZ$638
includes taxes & fees
4 Oct - 5 Oct
3-bedroom Cozy Home Close to Santa Claus, IN and 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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Top Winslow Hotel Reviews

Holiday Inn Express & Suites Evansville North by IHG

Holiday Inn Express & Suites Evansville North by IHG

10/10 Excellent
"Clean and would stay again."
Tyler 1-night trip
Posted 1 day ago
Holiday Inn Express & Suites Evansville North by IHG

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 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 NZ$325 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?

Large Home Sleeps 24 in Santa Claus 5 Mins from Holiday World with a Game Room: This holiday home rental outside of Winslow offers a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 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.