Winthrop Vacations from $935

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The Latest Winthrop vacation packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Waterloo, IA

Motel 6 Waterloo, IA

2 out of 5
Price was $967, price is now $935 per person
$935
per person
Dec 22 - Dec 26
found 20 hours ago
Roundtrip non-stop flight included
White Plains (HPN) to Waterloo (ALO)
5.8/10 (319 reviews)
The motel was closed due to water damage.

Reviewed on Oct 13, 2026

Isle Casino Hotel Waterloo Hotel & Casino - A Caesars Rewards Destination

Isle Casino Hotel Waterloo Hotel & Casino - A Caesars Rewards Destination

3 out of 5
Price was $1,054, price is now $1,002 per person
$1,002
per person
Dec 22 - Dec 26
found 20 hours ago
Roundtrip non-stop flight included
White Plains (HPN) to Waterloo (ALO)
8.4/10 Very Good! (1,007 reviews)

The Black Hawk Hotel

The Black Hawk Hotel

3.5 out of 5
Price was $1,190, price is now $1,147 per person
$1,147
per person
Dec 22 - Dec 26
found 20 hours ago
Roundtrip non-stop flight included
White Plains (HPN) to Waterloo (ALO)
9.2/10 Wonderful! (932 reviews)

Executive Residency By Best Western Waterloo & Cedar Falls

Executive Residency By Best Western Waterloo & Cedar Falls

3 out of 5
Price was $1,052, price is now $1,025 per person
$1,025
per person
Dec 22 - Dec 26
found 20 hours ago
Roundtrip non-stop flight included
White Plains (HPN) to Waterloo (ALO)
8.8/10 Excellent! (65 reviews)
Jennifer and Wendy at the front desk were so helpful and friendly. The rooms were clean and comfortable and the breakfast was also delicious!

Reviewed on Oct 20, 2026

Best Western Plus Waterloo & Cedar Falls

Best Western Plus Waterloo & Cedar Falls

2.5 out of 5
Price was $1,048, price is now $1,021 per person
$1,021
per person
Dec 22 - Dec 26
found 20 hours ago
Roundtrip non-stop flight included
White Plains (HPN) to Waterloo (ALO)
8.6/10 Excellent! (601 reviews)

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Winthrop Hotel Deals

Urbana Inn & Suites

Urbana Inn & Suites

2.5 out of 5
5369 Hutton Drive Urbana IA
$79 nightly
The price is $83 total per night from Dec 1 to Dec 2
$83 total
Dec 1 - Dec 2
Total with taxes and fees
8.2/10 Very Good! (492 reviews)
"Room was smelly and ice machine was broken. Price was good and staff was friendly."

Reviewed on Nov 9, 2026

Urbana Inn & Suites
Cobblestone Inn & Suites – Manchester

Cobblestone Inn & Suites – Manchester

3.5 out of 5
1210 Commercial Court Manchester IA
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $129 total per night from Dec 3 to Dec 4
$129 total
Dec 3 - Dec 4
Total with taxes and fees
9/10 Wonderful! (427 reviews)
"Very well kept property. Clean rooms and great breakfast. Will stay there in the future."

Reviewed on Nov 9, 2026

Cobblestone Inn & Suites – Manchester
Cornerstone Inn & Suites

Cornerstone Inn & Suites

2.5 out of 5
421 Rock Island Road Oelwein IA
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $108 total per night from Dec 11 to Dec 12
$108 total
Dec 11 - Dec 12
Total with taxes and fees
Cornerstone Inn & Suites
See all 58 properties in Winthrop
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 Winthrop Vacation Packages

Winthrop Essential Information

Language
English
Currency
U.S dollars
Population
850
Max Temp Winter
25ºF
Max Temp Summer
80ºF

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Frequently asked questions

How much does a Winthrop vacation package cost?
You'll find cheap prices from $935 on Expedia for your Winthrop getaway. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Winthrop costs.
What are the cheapest months to go to Winthrop?
December, January and February are the best times to look for cheap Winthrop vacation packages. Traveling in quieter months means you can typically find lower prices on flights and accommodations.
How many days is enough for Winthrop?
Generally, a handful of days is enough to check out the major attractions during your Winthrop vacation. But if you'd like to have some time to rest or take day tours, consider extending your trip.
How to find the best Winthrop package deals?
Use Expedia's handy filters to help you find some fabulous Winthrop package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Winthrop package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Winthrop vacation as a package?
You can enjoy significant savings on your Winthrop break by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to see some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winthrop?
If you're considering a spur-of-the-moment Winthrop adventure, check out 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 land amazing deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Winthrop vacation packages?
Set off on your perfect trip to Winthrop with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or hold off until payday — we've partnered with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to budget for your trip and snap up travel deals before they sell out.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.