Winslow Vacations from $513

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The Latest Winslow vacation packages

Price found within the past 48 hours. Click for updated prices.
PT6 INN

PT6 INN

2.5 out of 5
Price was $541, price is now $513 per person
$513
per person
Jul 24 - Jul 26
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Evansville (EVV)
4.6/10 (105 reviews)
Staff was nice and friendly

Reviewed on Nov 12, 2025

Holiday Inn Express Evansville West by IHG

Holiday Inn Express Evansville West by IHG

2.5 out of 5
Price was $655, price is now $601 per person
$601
per person
Jul 24 - Jul 26
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Evansville (EVV)
8.6/10 Excellent! (572 reviews)
A pleasant stay before my flight.

Reviewed on May 9, 2026

New Harmony Inn Resort and Conference Center

New Harmony Inn Resort and Conference Center

3 out of 5
Price was $622, price is now $577 per person
$577
per person
Jul 24 - Jul 26
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Evansville (EVV)
9/10 Wonderful! (523 reviews)
We had problems with the keycards and the door mechanism. There wasn’t enough staff to help us with the problem or even come to the room to check it out. The pool area was pretty poor shape. The town and the food was wonderful.

Reviewed on Apr 27, 2026

Fairfield Inn By Marriott Evansville East

Fairfield Inn By Marriott Evansville East

3 out of 5
Price was $590, price is now $558 per person
$558
per person
Jul 24 - Jul 26
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Evansville (EVV)
8.6/10 Excellent! (496 reviews)
Clean rooms and friendly front desk staff. Great price for for the room

Reviewed on May 10, 2026

Envi Boutique Hotel Henderson-Evansville South

Envi Boutique Hotel Henderson-Evansville South

3 out of 5
Price was $612, price is now $581 per person
$581
per person
Jul 24 - Jul 26
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Evansville (EVV)
7.8/10 Good! (306 reviews)
Very clean and elegant would highly recommend even for a weekend getaway perfect !!!

Reviewed on Apr 19, 2026

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Winslow Hotel Deals

Comfort Inn Ferdinand

Comfort Inn Ferdinand

2.5 out of 5
123 Scenic Hills Court Ferdinand IN
Fully refundable
$106 nightly
The price is $118 total per night from May 26 to May 27
$118 total
May 26 - May 27
Total with taxes and fees
8.4/10 Very Good! (658 reviews)
"Only complaint the pool area there were some artificial eye lashes and a couple balls of hair on the concrete floor by the pool which was a bit of a turn off but otherwise everything was good!"

Reviewed on May 22, 2026

Comfort Inn Ferdinand
Baymont by Wyndham Washington

Baymont by Wyndham Washington

2.5 out of 5
7 Cumberland Dr Washington IN
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $137 total per night from Jun 14 to Jun 15
$137 total
Jun 14 - Jun 15
Total with taxes and fees
8.2/10 Very Good! (700 reviews)
"Old food still in fridge from some other person stay. Sink wouldn’t drain, breakfast was out of everything & over 1 1/2!hour left on time"

Reviewed on May 18, 2026

Baymont by Wyndham Washington
Fairfield Inn & Suites Jasper

Fairfield Inn & Suites Jasper

3 out of 5
333 River Centre Landing Jasper IN
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $160 total per night from May 31 to Jun 1
$160 total
May 31 - Jun 1
Total with taxes and fees
9.2/10 Wonderful! (407 reviews)
"Clean Helpful staff"

Reviewed on May 21, 2026

Fairfield Inn & Suites Jasper
See all 82 properties in Winslow
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

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Frequently asked questions

How much does a Winslow vacation package cost?
You can snap up a vacation package to this top destination from $513 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.