Winslow Vacations from $578

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The Latest Winslow Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A hotel room with a bed, a chair, a TV, a desk, and a bathtub.
    Jan 7 - Jan 10

    Rodeway Inn Mount Vernon, IN + Flight

    Mount Vernon
    3 nights
    2.0 star property
    6.0/10 - (180 reviews)
    Roundtrip • Oklahoma City (OKC) - Evansville (EVV)
    OKC - EVV • 1 stop EVV - OKC • 1 stop
    $621
    $578
    per traveler
    found 1 day ago
    Rodeway Inn Mount Vernon, IN
  • A modern hotel room with a sofa, desk, TV, and dining area.
    Jan 7 - Jan 10

    Residence Inn by Marriott Evansville East + Flight

    Evansville
    3 nights
    3.0 star property
    8.6/10 - Excellent (578 reviews)
    Roundtrip • Oklahoma City (OKC) - Evansville (EVV)
    OKC - EVV • 1 stop EVV - OKC • 1 stop
    $709
    $604
    per traveler
    found 1 day ago
    Residence Inn by Marriott Evansville East
  • A cozy living room with a fireplace, wooden furniture, and artwork on the walls.
    Jan 7 - Jan 10

    New Harmony Inn Resort and Conference Center + Flight

    New Harmony
    3 nights
    3.0 star property
    9.0/10 - Wonderful (580 reviews)
    "Our room had the most comfortable bed I have slept on in a long time. The room was clean and had everything needed. The only drawback to this hotel is that it is ageing, so the elevator rattles, the hallways are dark, and the room key cards are unreliable (the desk clerk warned us to keep them away from phones and other electronics, but even though we did, one stopped working). That said, the hotel is in a perfect and beautiful location, and we would stay there again."
    Reviewed October 25, 2026
    Roundtrip • Oklahoma City (OKC) - Evansville (EVV)
    OKC - EVV • 1 stop EVV - OKC • 1 stop
    $725
    $640
    per traveler
    found 1 day ago
    New Harmony Inn Resort and Conference Center
  • An outdoor patio with a fire feature, seating, and a view of a lake.
    Jan 7 - Jan 10

    Hampton Inn Evansville + Flight

    Evansville
    3 nights
    3.0 star property
    8.8/10 - Excellent (1,000 reviews)
    "The staff were friendly in the rooms were very nice."
    Reviewed November 2, 2026
    Roundtrip • Oklahoma City (OKC) - Evansville (EVV)
    OKC - EVV • 1 stop EVV - OKC • 1 stop
    $721
    $669
    per traveler
    found 1 day ago
    Hampton Inn Evansville
  • A modern hotel with a glass facade, a covered entrance, and a sign reading "HYATT PLACE".
    Jan 7 - Jan 10

    Hyatt Place Evansville + Flight

    Downtown Evansville
    3 nights
    3.0 star property
    9.4/10 - Exceptional (1,000 reviews)
    "The breakfast was VERY poorly managed. They didn't restock items as they ran out. No plates, no glasses, and at one point we took it upon ourselves to get in the storage cabinet below to retrieve creamer for our coffee. When we did that, the front desk person just glared at us like we were doing something wrong and asked very snarkily if there's something they could help us with. Then they charged us an incidental fee when we arrived of $50 which is is normal, but when the transaction updated,..."
    Reviewed November 2, 2026
    Roundtrip • Oklahoma City (OKC) - Evansville (EVV)
    OKC - EVV • 1 stop EVV - OKC • 1 stop
    $729
    $679
    per traveler
    found 1 day ago
    Hyatt Place Evansville

Winslow Hotel Deals

A hotel with a modern design, featuring a spacious parking lot and a well-lit entrance.

Comfort Inn Jasper South

Comfort Inn Jasper South
2.5 star property
14.6 mi from Winslow
9.2 out of 10, Wonderful, (668 reviews)
$102 nightly
The price is $114
Nov 26 - Nov 27
Total with taxes and fees
Comfort Inn Jasper South
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.
See all properties in Winslow

Frequently Asked Questions

How much does a Winslow vacation package cost?

You can snap up a vacation package to this top destination from $578 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.