Default HTG hotel image

Winslow Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winslow vacation rentals

Property grounds

1. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (24 reviews)
"Great setting, good beds, and clean!"
United States
Doug W.
$233 nightly
The price is $261
Sep 17 - Sep 18
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
Outdoor dining

2. 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 traveler
$206 nightly
The price is $231
Sep 17 - Sep 18
Total with taxes and fees
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.
$239 nightly
The price is $268
Sep 17 - Sep 18
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
TV

4. Yellow Banks Log Cabin with Lake Views

Yellow Banks Log Cabin with Lake Views
Dale
8.8 out of 10, Excellent, (29 reviews)
"Great cabin! Comfy beds."
United States
Kelly G.
$265 nightly
The price is $297
Sep 20 - Sep 21
Total with taxes and fees
Yellow Banks Log Cabin with Lake Views
Interior

5. 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.
$174 nightly
The price is $195
Sep 17 - Sep 18
Total with taxes and fees
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Exterior

6. 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.
$261 nightly
The price is $292
Sep 23 - Sep 24
Total with taxes and fees
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
Smart TV

7. Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (73 reviews)
"The place was great, quiet and peaceful! "
United States
brian k.
$155 nightly
The price is $174
Sep 17 - Sep 18
Total with taxes and fees
Guest House with acreage to explore.
Outdoor dining

8. 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.
$233 nightly
The price is $261
Sep 17 - Sep 18
Total with taxes and fees
Yellow Banks Log Cabin With Waterfront Views
Smart TV

9. 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, (33 reviews)
"Great value"
United States
ERIC
$279 nightly
The price is $324
Sep 20 - Sep 21
Total with taxes and fees
Cozy East Side Condo in Washington close to City Park and Hospital
House (2 Bedrooms) | Interior

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

The Cowboys Slumber' 2 Mi to Lincoln State Park
3.0 star property
Gentryville
$352 nightly
The price is $394
Sep 21 - Sep 22
Total with taxes and fees
The Cowboys Slumber' 2 Mi to Lincoln State Park
TV

11. 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.
$361 nightly
The price is $404
Sep 21 - Sep 22
Total with taxes and fees
The Cowboys Slumber' 2 Mi to Lincoln State Park
Smart TV

12. Family Friendly Lakehouse with great views!

Family Friendly Lakehouse with great views!
Jasper
10.0 out of 10, Exceptional, (12 reviews)
"Very beautiful and comfortable house for our stay"
United States
James S.
$354 nightly
The price is $396
Sep 21 - Sep 22
Total with taxes and fees
Family Friendly Lakehouse with great views!
Coffee/tea maker, fridge, microwave, oven

13. 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, (33 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
$374 nightly
The price is $419
Oct 4 - Oct 5
Total with taxes and fees
5 Miles from Holiday World sleeps 11+ —Family Escape
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, (4 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.
$313 nightly
The price is $351
Sep 17 - Sep 18
Total with taxes and fees
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.
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

Comfort Inn Jasper South

Comfort Inn Jasper South

10/10 Excellent
"Great breakfast, clean rooms. Kids loved the arcade area."
Carrie 1-night trip
Posted 20 hours ago
Comfort Inn Jasper South

Find out more about Winslow

Everything you need to know about Winslow vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winslow vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winslow vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winslow in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $174 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winslow rentals

At Expedia, we put the best Winslow vacation 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 vacation.

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 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, Dubois County Museum, and Jasper City Mill. Sultan's Run Golf Course 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.