Winslow Vacations from $415
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The Latest Winslow Vacation Packages
- Little Daisy Motel
Aug 26 - Aug 29Little Daisy Motel + Flight
Cottonwood3 nights2.0 star property9.6/10 - Exceptional (444 reviews)"Great small business with clean rooms. It's not fancy, but very clean and great staff."Reviewed June 27, 2026Roundtrip • New York (NYC) - Flagstaff (FLG)JFK - PHX • Nonstop PHX - LGA • 1 stop$528$415found 1 day agoper traveler - Maswik Lodge - Inside the Park
Aug 15 - Aug 20Maswik Lodge - Inside the Park + Flight
Grand Canyon5 nights2.5 star property9.0/10 - Wonderful (4,021 reviews)"We had a very nice room in the south part of Maswik. Ate Pizza at the pizza pub and it was great but pretty pricey."Reviewed July 17, 2026Roundtrip • Chicago (CHI) - Flagstaff (FLG)ORD - FLG • 1 stop FLG - ORD • 1 stop$1,274$1,005found 1 day agoper traveler - Bespoke Inn Flagstaff
Oct 8 - Oct 12Bespoke Inn Flagstaff + Flight
Downtown Flagstaff4 nights4.0 star property9.8/10 - Exceptional (411 reviews)Roundtrip • Atlanta (ATL) - Flagstaff (FLG)ATL - FLG • 1 stop FLG - ATL • 1 stop$2,198$1,750found 1 day agoper traveler - Club Wyndham Flagstaff
Aug 15 - Aug 20Club Wyndham Flagstaff + Flight
Flagstaff5 nights3.5 star property9.0/10 - Wonderful (598 reviews)"The room was spacious, privacy was awesome. Staff was very accommodating, on site amenities were amazing. We will Definitely make this our go to place to stay when ever visiting northern Az."Reviewed July 14, 2026Roundtrip • Chicago (CHI) - Flagstaff (FLG)ORD - FLG • 1 stop FLG - ORD • 1 stop$1,249$995found 1 day agoper traveler - The View Motel
Sep 18 - Sep 24The View Motel + Flight
Cottonwood6 nights2.5 star property9.0/10 - Wonderful (664 reviews)Roundtrip • Boston (BOS) - Flagstaff (FLG)BOS - PHX • Nonstop PHX - BOS • 1 stop$857$714found 1 day agoper traveler
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Frequently Asked Questions
How much does a Winslow vacation package cost?
You can grab a vacation package to this top destination from $415 on Expedia. But how much your vacation to Winslow costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Winslow?
If you're hoping to book a cheap Winslow vacation package, consider traveling in February, April and September. You'll usually find better rates on flights and accommodations during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Winslow?
With a well-planned itinerary, you can easily hit the most popular Winslow attractions in a handful of days. But if you want to explore off the beaten track or go on day trips, think about booking your Winslow vacation for longer.
Is it worth booking a vacation package to Winslow?
Winslow offers everything you need for an amazing trip. Get your Winslow vacation off to a flying start by exploring major attractions like Standin' on the Corner Park.
How to find the best Winslow package deals?
Use Expedia's filters to help you find some tempting Winslow package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Winslow package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Winslow vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking accommodations and flights separately. Better still, you can customize your Winslow trip to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Winslow?
Enjoy incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Winslow break.
Does Expedia offer Book Now, Pay Later Winslow vacation packages?
Set off on your dream getaway to Winslow with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait for payday — we've partnered with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stay on budget and snag great deals before they sell out.