Winslow Holiday Rentals

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Holiday Rentals in Winslow

Guest House with acreage to explore.

Tennyson
9.6 out of 10, Exceptional, (59)
"Stayed here for a long weekend getaway to Interlake to off-road. Had the best time and Doug was a great host. Will be returning"
United States
tasha k.
The price is NZ$280
includes taxes & fees
15 Nov - 16 Nov
Guest House with acreage to explore.

Tranquil Hideaway: Your Private Lakefront Retreat

Dale
9.2 out of 10, Wonderful, (11)
"This was perfect for us. We wanted to stay close to Holiday World and Splashing Safari. We enjoyed the secluded area. The house large enough for 2 adults and 2 kids. The kitchen was well equipped for the few meals we made there. Overall a nice stay, and would definitely rebook."
United States
MICHELLE B.
The price is NZ$471
includes taxes & fees
19 Nov - 20 Nov
Tranquil Hideaway: Your Private Lakefront Retreat

Yellow Banks Log Cabin With Waterfront Views

Dale
9.2 out of 10, Wonderful, (13)
"Great cabin. Rugs and couch was really dirty. Hair was all over. Other than that is was great"
United States
Nicholas S.
The price is NZ$420
includes taxes & fees
17 Nov - 18 Nov
Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views

Dale
10.0 out of 10, Exceptional, (17)
"Cute little cabin next to a small pond "
United States
Lisa H.
The price is NZ$418
includes taxes & fees
16 Nov - 17 Nov
Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views

Dale
9.6 out of 10, Exceptional, (20)
"Great quiet place"
United States
Sherry L.
The price is NZ$418
includes taxes & fees
16 Nov - 17 Nov
Yellow Banks Log Cabin With Waterfront Views

Historic Home by Dogwood Lake/Glendale

Montgomery
10.0 out of 10, Exceptional, (6)
"Nice place in the country. "
United States
Bruce H.
Historic Home by Dogwood Lake/Glendale

5 Miles from Holiday World sleeps 11+ —Family Escape

Dale
9.4 out of 10, Exceptional, (11)
"Absolutely amazing host, they made the check in process so easy. It was minutes from Holiday World so it made our trip so well worth it. The house was beautiful and the game room was the favorite part of the kid’s night. "
United States
Sabrina S.
The price is NZ$675
includes taxes & fees
18 Nov - 19 Nov
5 Miles from Holiday World sleeps 11+ —Family Escape

Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Huntingburg
9.8 out of 10, Exceptional, (19)
"The unit was clean, with tons of amenities, including a lot of activities for kids. Great hosts. No complaints "
United States
Jon
The price is NZ$350
includes taxes & fees
16 Nov - 17 Nov
Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Truelove Chalet- A Relaxed, Rustic, Glam Cabin!

Loogootee
9.4 out of 10, Exceptional, (10)
"We stayed here for 2 nights during our elopement and it was the cutest little house.. nice, quiet area with beautiful scenery. The host were amazing to talk to "
United States
Brittany N.
Truelove Chalet- A Relaxed, Rustic, Glam Cabin!

Another Oasis just 6 miles from Holiday World

Gentryville
9.0 out of 10, Wonderful, (19)
"Stayed in this house for an extended weekend with the family. We went to Holiday world Friday which was an easy 10 minute drive from the house. The house was clean and comfortable with plenty of room to spread out. Would definitely stay here again."
United States
Kristine L.
Another Oasis just 6 miles from Holiday World

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

2.0 star property
Lynnville
10.0 out of 10, Exceptional, (8)
"Cute quiet lil house located around attractions for families. Well worth the money and host is always available "
United States
Madison B.
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water

Yellow Banks Log Cabin with Lake Views

Dale
8.8 out of 10, Excellent, (19)
"Nice secluded area, very tranquil setting "
United States
Derek M.
The price is NZ$476
includes taxes & fees
2 Dec - 3 Dec
Yellow Banks Log Cabin with Lake Views

X Marks the Spot(Blue)1.5 miles from Holiday World

Carter Township
9.8 out of 10, Exceptional, (15)
"Close to everything we wanted to do. Owner was responsive and house was stocked and clear instructions on check out."
United States
JOSHUA
X Marks the Spot(Blue)1.5 miles from Holiday World

Yellow Banks Log Cabin With Waterfront Views

Dale
10.0 out of 10, Exceptional, (7)
"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$487
includes taxes & fees
19 Nov - 20 Nov
Yellow Banks Log Cabin With Waterfront Views

Near Hiking & Fishing: Dale Home w/ Deck!

3.0 star property
Dale
Near Hiking & Fishing: Dale Home w/ Deck!

X Marks the Spot(Yellow)1.5 mi. from Holiday World

Carter Township
9.6 out of 10, Exceptional, (13)
"It was close to Holiday World. It was clean and good place to stay.Amy was nice."
United States
Patrick G.
X Marks the Spot(Yellow)1.5 mi. from Holiday World

Chestnut Street Retreat

Huntingburg
10.0 out of 10, Exceptional, (46)
"We loved our stay at the home and we will definitely return again on our next trip to Huntingburg"
United States
Rick B.
Chestnut Street Retreat

X Marks the Spot(Orange)1.5 miles fromHolidayWorld

Carter Township
10.0 out of 10, Exceptional, (1)
"Great place to stay, especially for Holiday World with it only being a few minutes down the road! Clean, organized, and had everything we needed plus some (games, books, etc). Loved seeing the goats out the window next door & our kids loved saying hi to them. Utilized the grilling area as well! "
United States
Heidi H.
X Marks the Spot(Orange)1.5 miles fromHolidayWorld

The Family Oasis just 6 miles from Holiday World

Gentryville
9.2 out of 10, Wonderful, (45)
"Great place. Great Location. Great Communication. Easy check in. We will return and stay here again for another trip to Holiday World! "
United States
Cera P.
The Family Oasis just 6 miles from Holiday World

Eagles Nest - Eagle Adventures LLC

Ferdinand
Eagles Nest - Eagle Adventures LLC
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

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$280 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?

Tranquil Hideaway: Your Private Lakefront Retreat: This holiday home rental outside of Winslow is located on the waterfront, and has a fireplace, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.