Default HTG hotel image

Winslow Holiday 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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Winslow holiday rentals

Outdoor dining

1. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (30 reviews)
"Very nice cabin very clean overall really enjoyed"
United States
Addy D.
The price is AU$350
includes taxes & fees
9 Aug - 10 Aug
Yellow Banks Log Cabin With Waterfront Views
Property grounds

2. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (21 reviews)
"Great setting, good beds, and clean!"
United States
Doug W.
The price is AU$392
includes taxes & fees
5 Aug - 6 Aug
Yellow Banks Log Cabin With Waterfront Views
Exterior

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 AU$396
includes taxes & fees
4 Aug - 5 Aug
Yellow Banks Log Cabin With Waterfront Views
Interior

4. 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, (28 reviews)
"Great place to stay for a few days if you're visiting Holiday World or the area. "
United States
Brandon S.
The price is AU$280
includes taxes & fees
17 Aug - 18 Aug
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
TV

5. Yellow Banks Log Cabin with Lake Views

Yellow Banks Log Cabin with Lake Views
Dale
8.8 out of 10, Excellent, (26 reviews)
"Cute little cabin, fun for kids. "
United States
Paul S.
The price is AU$433
includes taxes & fees
5 Aug - 6 Aug
Yellow Banks Log Cabin with Lake Views
Smart TV

6. Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (71 reviews)
"The place was great, quiet and peaceful! "
United States
brian k.
The price is AU$263
includes taxes & fees
7 Aug - 8 Aug
Guest House with acreage to explore.
Smart TV

7. 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, (31 reviews)
"Great value"
United States
ERIC
The price is AU$455
includes taxes & fees
4 Aug - 5 Aug
Cozy East Side Condo in Washington close to City Park and Hospital
House (2 Bedrooms) | Interior

8. 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 AU$542
includes taxes & fees
17 Aug - 18 Aug
The Cowboys Slumber' 2 Mi to Lincoln State Park
Outdoor dining

9. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
8.8 out of 10, Excellent, (15 reviews)
"Excellent cabins! We had so much fun!!!"
United States
Leslie H.
The price is AU$388
includes taxes & fees
4 Aug - 5 Aug
Yellow Banks Log Cabin With Waterfront Views
1 bedroom, iron/ironing board, free WiFi, bed sheets

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

Princeton Suite 7 - QUEEN 1BD/1BA Apt
Princeton
The price is AU$253
includes taxes & fees
7 Aug - 8 Aug
Princeton Suite 7 - QUEEN 1BD/1BA Apt
TV

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

The Cowboys Slumber' 2 Mi to Lincoln State Park
Gentryville
The price is AU$532
includes taxes & fees
17 Aug - 18 Aug
The Cowboys Slumber' 2 Mi to Lincoln State Park
Exterior

12. 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, (15 reviews)
"Cute quiet lil house located around attractions for families. Well worth the money and host is always available "
United States
Madison B.
The price is AU$523
includes taxes & fees
11 Aug - 12 Aug
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
Smart TV

13. Family Friendly Lakehouse with great views!

Family Friendly Lakehouse with great views!
Jasper
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay for family! Great gathering place for family and friends! Everything you would need and more!"
United States
Jill C.
The price is AU$656
includes taxes & fees
10 Aug - 11 Aug
Family Friendly Lakehouse with great views!
Exterior

14. 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, (2 reviews)
"Very cozy and clean place! It was perfect for our group of five, including three teenagers, while we visited Holiday World. Shane is a wonderful host, and the thoughtful touches - like the selection of snacks - made us feel especially welcome. Communication was easy throughout our stay. I was also fascinated by the historical books displayed on the shelves - they were such a unique and memorable touch, adding to a very historic feel of the place and the town. "
United States
Svitlana T.
The price is AU$510
includes taxes & fees
30 Aug - 31 Aug
3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
Coffee/tea maker, fridge, microwave, oven

15. 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, (28 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
The price is AU$749
includes taxes & fees
2 Sept - 3 Sept
5 Miles from Holiday World sleeps 11+ —Family Escape
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

Jasper Inn

Jasper Inn

8/10 Good
"Small town Inn vibes. Some rooms updated and some not. Breakfast had good options. Overall we liked our stay and would stay again."
Gretchen 2-night trip
Posted 4 hours ago
Jasper Inn

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$263 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?

The Cowboys Slumber' 2 Mi to Lincoln State Park: This holiday home rental outside of Winslow offers a patio, 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, Dubois County Museum and St Joseph's Church. Jasper City Mill and Sultan's Run 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.