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Winslow Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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 CA $176
CA $337 total
includes taxes & fees
Oct 22 - Oct 23
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.

2. 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 CA $211
CA $387 total
includes taxes & fees
Oct 22 - Oct 23
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 CA $218
CA $397 total
includes taxes & fees
Oct 22 - Oct 23
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.

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, (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 CA $139
CA $274 total
includes taxes & fees
Oct 22 - Oct 23
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
A cozy cabin interior with a sofa, dining table, and chairs.

5. 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 CA $246
CA $433 total
includes taxes & fees
Oct 22 - Oct 23
Yellow Banks Log Cabin with Lake Views
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)
"Doug is a wonderful host who goes the extra mile to make sure you are comfortable and enjoy your stay. His property is amazing, clean, and quiet. This was our third stay and we will definitely be back again and again."
United States
tasha k.
The price is CA $201
CA $258 total
includes taxes & fees
Oct 22 - Oct 23
Guest House with acreage to explore.
A spacious living area with a white leather sofa, a wooden staircase, and a brick fireplace.

7. Truelove Chalet- A Relaxed, Rustic, Glam Cabin!

Truelove Chalet- A Relaxed, Rustic, Glam Cabin!
Loogootee
9.4 out of 10, Exceptional, (13 reviews)
"It was clean, bright with great views all around."
United States
Taylor K.
The price is CA $113
CA $321 total
includes taxes & fees
Oct 22 - Oct 23
Truelove Chalet- A Relaxed, Rustic, Glam Cabin!
A two-story house with a front porch, two chairs, and a stone pillar.

8. 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 cool old house but clean and tidy everything was great"
United States
Robert Y.
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
A bedroom with a wooden wall panel, a bed with white bedding, and a small shelf with decorative items.

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

Princeton Suite 7 - QUEEN 1BD/1BA Apt
Princeton
The price is CA $98
CA $227 total
includes taxes & fees
Oct 25 - Oct 26
Princeton Suite 7 - QUEEN 1BD/1BA Apt
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 CA $211
CA $387 total
includes taxes & fees
Oct 22 - Oct 23
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.

11. 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 CA $211
CA $554 total
includes taxes & fees
Oct 22 - Oct 23
The Cowboys Slumber' 2 Mi to Lincoln State Park
A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

12. 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, (2 reviews)
"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 CA $155
CA $569 total
includes taxes & fees
Oct 22 - Oct 23
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.

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, (37 reviews)
"Great value"
United States
ERIC
The price is CA $203
CA $450 total
includes taxes & fees
Nov 4 - Nov 5
Cozy East Side Condo in Washington close to City Park and Hospital
A spacious living room with a fireplace, a large window, and a high ceiling with exposed beams.

14. 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 CA $460
CA $589 total
includes taxes & fees
Nov 3 - Nov 4
Family Friendly Lakehouse with great views!
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.

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, (35 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
The price is CA $348
CA $580 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.

16. 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 CA $336
CA $521 total
includes taxes & fees
Oct 22 - Oct 23
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

Quality Inn Huntingburg - Jasper

Quality Inn Huntingburg - Jasper

8/10 Good
"Friendly staff. Clean property. Comfortable bed. Clean bathroom. Good breakfast. Great value."
Gregory 2-night trip
Posted 1 day ago
Quality Inn Huntingburg - Jasper

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winslow vacation rentals we have selected for you start as low as CA $258 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 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, 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.