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A rocky outcrop with a small wooden structure on top, surrounded by autumn foliage.
Photo by Jessica Richter
Open Photo by Jessica Richter

Winslow Vacations from $421

Book a Hotel + Flight or Car together to unlock savings

The Latest Winslow Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Oct 9 - Oct 11

    Hotel O Eureka Springs - Christ Of Ozark Area + Flight

    Eureka Springs
    2 nights
    2.0 star property
    7.2/10 - Good (829 reviews)
    "The sheets were clean. The bathroom was clean. However the floor was not completely swept. The continental breakfast was not very good, it would have been nice to have some toast."
    Reviewed July 27, 2026
    Roundtrip • Chicago (ORD) - Fayetteville (XNA)
    ORD - XNA • 1 stop XNA - ORD • 1 stop
    $474
    $421
    per traveler
    found 12 hours ago
    Hotel O Eureka Springs - Christ Of Ozark Area
  • Front of property
    Oct 9 - Oct 11

    Inn at Rose Hall + Flight

    Eureka Springs Historic District
    2 nights
    3.0 star property
    9.2/10 - Wonderful (75 reviews)
    "Loved our stay! The house and room was very nice, the breakfast delicious, and the owner fabulous. Great location. Would highly recommend."
    Reviewed July 27, 2026
    Roundtrip • Chicago (ORD) - Fayetteville (XNA)
    ORD - XNA • 1 stop XNA - ORD • 1 stop
    $766
    $657
    per traveler
    found 12 hours ago
    Inn at Rose Hall
  • Gazebo
    Oct 9 - Oct 11

    Evening Shade Inn + Flight

    Eureka Springs
    2 nights
    3.5 star property
    10/10 - Exceptional (66 reviews)
    Roundtrip • Chicago (ORD) - Fayetteville (XNA)
    ORD - XNA • 1 stop XNA - ORD • 1 stop
    $551
    $487
    per traveler
    found 12 hours ago
    Evening Shade Inn
  • Front of property
    Oct 9 - Oct 11

    Rock Cottage Gardens B&B + Flight

    Eureka Springs Historic District
    2 nights
    3.0 star property
    9.4/10 - Exceptional (244 reviews)
    "Wonderful property, food & the staff was friendly & hospitable! Thanks, we hope to stay again in the future, John & Cindy Peters, Amarillo, TX"
    Reviewed June 30, 2026
    Roundtrip • Chicago (ORD) - Fayetteville (XNA)
    ORD - XNA • 1 stop XNA - ORD • 1 stop
    $703
    $624
    per traveler
    found 12 hours ago
    Rock Cottage Gardens B&B
  • Sauna
    Oct 9 - Oct 11

    Forest Springs Resort + Flight

    Eureka Springs
    2 nights
    2.0 star property
    9.2/10 - Wonderful (67 reviews)
    "cutest place! had so much to do there, so close to everything, will definitely be back whenever we visit eureka springs!"
    Reviewed July 26, 2026
    Roundtrip • Chicago (ORD) - Fayetteville (XNA)
    ORD - XNA • 1 stop XNA - ORD • 1 stop
    $666
    $598
    per traveler
    found 12 hours ago
    Forest Springs Resort

Winslow Hotel Deals

Hallway

Beard and Lady Inn

Beard and Lady Inn
3.0 star property
8.7 mi from Winslow
9.2 out of 10, Wonderful, (51 reviews)
"Probably the coolest place I have ever spent the night. I stayed in 1 Writer's block and it was very quaint. Thunderstorms that night lit up the room every so often. Beautiful place."
$98 nightly
The price is $109
Aug 9 - Aug 10
Total with taxes and fees
Beard and Lady Inn
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?

Offering excellent value package deals from $421 on Expedia, you'll be thrilled with how little a vacation to Winslow costs! Expedia's packages make travel planning easier and save you more.

What are the cheapest months to go to Winslow?

You can usually find lower prices and better availability in January, October and December. Browse our cheap Winslow vacation packages and you could land some great off-season deals.

How many days is enough for Winslow?

With a well-organized schedule, you can easily hit the top Winslow attractions in a few days. But if you'd like to venture off the beaten track or go on day tours, think about booking your Winslow vacation for longer.

How to find the best Winslow package deals?

Start your search for a Winslow package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Winslow package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Winslow escape underway.

Is it cheaper to book a Winslow vacation as a package?

Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Winslow vacation by choosing your preferred accommodation type, airline and car class.

When to book a vacation package to Winslow?

If you're considering an impromptu Winslow getaway, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking ahead.

Does Expedia offer Book Now, Pay Later Winslow vacation packages?

If you're like us, you love going away but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Winslow break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.