Winslow Vacations from $1,650
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Winslow vacation packages
Price found within the past 48 hours. Click for updated prices.
Envi Boutique Hotel Henderson-Evansville South
$1,756
per person
Oct 17 - Oct 23
found 7 hours ago
Roundtrip flight included
Zhengzhou (CGO) to Evansville (EVV)
7.8/10 Good! (323 reviews)
Some of the keys for the apartments wouldn't work. And charlie wouldn't bold it down and I had to flesh the tall by pulling the handle up on the chain other than that that everything was okay
Reviewed on Sep 8, 2026
Winslow Hotel Deals
Jasper Inn
951 Wernsing Road Jasper IN
8/10 Very Good! (840 reviews)
"We would stay again. Cheap and better than camping when its hot out. 3 Stars BAR IS JUST BEER AND ONLY OPEN AT LUNCH. NICE KITCHENETTE ROOMS ARE NOT PET FRIENDLY. Not a real arcade. Just a few games by the backdoor and the prizes have not been stocked in years it looks like. Restroom by front desk ..."
Reviewed on Sep 12, 2026
Comfort Inn Ferdinand
123 Scenic Hills Court Ferdinand IN
Fully refundable
$88 nightly
$98 total
Oct 15 - Oct 16
Total with taxes and fees
8.2/10 Very Good! (753 reviews)
"We travel a lot and this was by far the worst hotel we have ever stayed at. When we got to the room the air conditioner was in pieces half on the wall and half on the floor. It did still blow air but every time it cycled on a horrible smell filled the room which already smelled musty to begin with. ..."
Reviewed on Sep 14, 2026
Comfort Inn Jasper South
1970 Hospitality Drive Jasper IN
Fully refundable
$103 nightly
$116 total
Oct 15 - Oct 16
Total with taxes and fees
9.2/10 Wonderful! (640 reviews)
"Great breakfast, clean rooms. Kids loved the arcade area."
Reviewed on Sep 15, 2026
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.
Find the Best Winslow Vacation Packages
Winslow Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Evansville Regional Airport (EVV) |
Population | 850 |
More vacations you might like
Frequently asked questions
How much does a Winslow vacation package cost?
You can snap up a vacation package to this top destination from $1,650 on Expedia. However, how much your vacation to Winslow costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Winslow?
You're likely to find lower rates and better availability in November, December and January. Explore our cheap Winslow vacation packages and you could score some great off-season discounts.
How many days is enough for Winslow?
Generally, a handful of days is enough to see the main attractions during your Winslow vacation. But if you want to have time to unwind or take day tours, think about extending your trip.
How to find the best Winslow package deals?
Use Expedia's filter tool to help you find some great Winslow package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Winslow package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Winslow vacation as a package?
You can enjoy significant savings on your next Winslow break by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to see the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winslow?
If you're considering a spontaneous Winslow trip, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Winslow vacation packages?
Your Winslow trip should be a relaxing escape from your busy life, not a reason for money worries. So to allow you a little more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
