Winthrop Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Winthrop

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
The price is S$160 per night from 11 Aug to 12 Aug
S$160
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (284 reviews)
"I really like this place. First time staying at cobblestone. If I had to complain about anything, I guess they could’ve had bigger coffee cups."

Reviewed on 7 Aug, 2025

Cobblestone Inn & Suites – Manchester
SureStay Hotel by Best Western Manchester

SureStay Hotel by Best Western Manchester

2.5 out of 5
1020 W Main St, Manchester, IA
Fully refundableReserve now, pay when you stay
The price is S$121 per night from 18 Aug to 19 Aug
S$121
18 Aug - 19 Aug
includes taxes & fees
7.2/10 Good! (430 reviews)
"Good night sleep. Very clean and comfortable."

Reviewed on 27 Jul, 2025

SureStay Hotel by Best Western 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
The price is S$115 per night from 10 Aug to 11 Aug
S$115
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (424 reviews)
"Stayed the night of Ragbrai. Property is well maintained clean and close/walking distance to the downtown area. Very good option. They also have washer/dryer available which came in very handy. Breakfast is served"

Reviewed on 6 Aug, 2025

Cornerstone Inn & Suites
See all 61 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.

Frequently asked questions

How much does a Winthrop holiday package cost?
You'll find cheap prices 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 holiday to Winthrop costs.
What are the cheapest months to go to Winthrop?
If you'd like to book a cheap Winthrop holiday package, consider planning a trip in January, February and November. You'll generally find lower prices on accommodation and flights during these months — ideal for a budget-friendly break.
How many days is enough for Winthrop?
The ideal length of your Winthrop holiday depends on what you'd like to do and see. Generally, a few days to a week will give you time to tick off all the leading sights and explore some hidden spots along the way.
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 holiday package as early as possible.
Is it cheaper to book a Winthrop holiday as a package?
You can enjoy significant savings on your Winthrop break by booking a personalised holiday 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 holiday 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.
How to plan a trip to Winthrop?

  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Winthrop.
  2. Figure out your budget: Make sure you have enough money to cover everything from food and transportation to airfares and activities. Your accommodation will probably be the biggest expense during your trip to Winthrop.
  3. Set the duration of your trip: Start by listing all the sights and activities you want to get to in Winthrop. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick a Winthrop holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.