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Winslow Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winslow vacation rentals

Exterior

1. 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, (3 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 ￥36,643
￥55,980 total
includes taxes & fees
Sep 15 - Sep 16
3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
Smart TV

2. 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.
The price is ￥47,989
￥58,728 total
includes taxes & fees
Sep 15 - Sep 16
Family Friendly Lakehouse with great views!
Interior

3. 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 ￥15,179
￥29,879 total
includes taxes & fees
Sep 22 - Sep 23
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Coffee/tea maker, fridge, microwave, oven

4. 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.
The price is ￥46,317
￥74,181 total
includes taxes & fees
Oct 1 - Oct 2
5 Miles from Holiday World sleeps 11+ —Family Escape
House (2 Bedrooms) | Interior

5. 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 ￥22,998
￥60,419 total
includes taxes & fees
Sep 16 - Sep 17
The Cowboys Slumber' 2 Mi to Lincoln State Park
TV

6. 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 ￥16,865
￥61,990 total
includes taxes & fees
Sep 21 - Sep 22
The Cowboys Slumber' 2 Mi to Lincoln State Park
TV

7. 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.
The price is ￥26,831
￥46,707 total
includes taxes & fees
Sep 16 - Sep 17
Yellow Banks Log Cabin with Lake Views
Exterior

8. 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 ￥23,765
￥42,930 total
includes taxes & fees
Sep 24 - Sep 25
Yellow Banks Log Cabin With Waterfront Views
Property grounds

9. 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.
The price is ￥22,998
￥40,354 total
includes taxes & fees
Sep 22 - Sep 23
Yellow Banks Log Cabin With Waterfront Views
Outdoor dining

10. 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
The price is ￥19,165
￥35,717 total
includes taxes & fees
Sep 22 - Sep 23
Yellow Banks Log Cabin With Waterfront Views
Smart TV

11. 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.
The price is ￥21,925
￥27,990 total
includes taxes & fees
Sep 21 - Sep 22
Guest House with acreage to explore.
Outdoor dining

12. 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 ￥22,998
￥41,728 total
includes taxes & fees
Sep 24 - Sep 25
Yellow Banks Log Cabin With Waterfront Views
Smart TV

13. 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
The price is ￥22,232
￥49,967 total
includes taxes & fees
Sep 12 - Sep 13
Cozy East Side Condo in Washington close to City Park and Hospital
Exterior

14. 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 ￥24,548
￥46,169 total
includes taxes & fees
Sep 28 - Sep 29
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
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

Comfort Inn Ferdinand

Comfort Inn Ferdinand

8/10 Good
"Decided to stay here cause it was getting late. Glad we found CI here. Great decision. . Spacious room-#101. Bath was large, clean, bright and way nicer than similarly priced hotels. Nice towels. Dog fee was only $25. AC was great. B’fast included waffle makers, precooked cheese omelette, sausage Pattie’s, biscuits/gravy. Chobani yogurt (no gluten) & another that was GF. Will definitely stay here on our next drive on I-64 west. Don’t know why some have rated it low."
Paul 1-night trip
Posted 1 hour ago
Comfort Inn Ferdinand

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 Buffalo Trace Golf Course 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.