Dickinson County Holidays

Photo by Erik Rowley

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The Annual Holiday Sale

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Top hotels in Dickinson County

Lake Okoboji Resort & Conference Center

Lake Okoboji Resort & Conference Center

3 out of 5
1405 Highway 71 Okoboji IA
Fully refundableReserve now, pay when you stay
The price is S$121 per night from 16 Mar to 17 Mar
S$121
16 Mar - 17 Mar
includes taxes & fees
7.8/10 Good! (925 reviews)
Clean Room and Breakfast was not great.

Reviewed on 8 Mar, 2026

Lake Okoboji Resort & Conference Center
Bridges Bay Resort

Bridges Bay Resort

3.5 out of 5
630 Linden Drive Arnolds Park IA
The price is S$124 per night from 16 Mar to 17 Mar
S$124
16 Mar - 17 Mar
includes taxes & fees
7.6/10 Good! (648 reviews)
Courteous staff. Dishwasher in our suite was broken so couldn't use it. No light at microwave. Very noisy with kids running up & down the hallways.

Reviewed on 24 Feb, 2026

Bridges Bay Resort
AmericInn by Wyndham Okoboji

AmericInn by Wyndham Okoboji

2.5 out of 5
1005 Brooks Park Dr Okoboji IA
Fully refundableReserve now, pay when you stay
The price is S$118 per night from 20 Mar to 21 Mar
S$118
20 Mar - 21 Mar
includes taxes & fees
9/10 Wonderful! (593 reviews)
Astonishingly good breakfast options

Reviewed on 8 Mar, 2026

AmericInn by Wyndham Okoboji
See all 425 properties in Dickinson County
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 Dickinson County holiday package cost?
Get set to book, because a trip to Dickinson County starts from a tempting . When you combine your flights, hotels and car rentals into a travel package, you'll pick up the best deals.
How do I get a cheap travel package to Dickinson County?
Creating your own Dickinson County holiday package with Expedia is one of the easiest ways to save. We have access to more than 550 air carriers and 1,000,000 hotels around the globe. With such an awesome range to pick from, you'll have no hassles creating your next dream getaway.
What are the top hotels in Dickinson County?
Check out Bridges Bay Resort and AmericInn by Wyndham Okoboji in Milford. Any good Dickinson County itinerary has to include a stop in this great city!
How far in advance should I book my Dickinson County holiday?
Search Expedia to compare international fares as soon as you've got your travel dates. In most cases, you can purchase a ticket up to 12 months before departure. If you don't see your preferred carrier, or you have to book last minute, don't worry. Cheap tickets to Dickinson County sometimes emerge within weeks of departure.
What does an Expedia Dickinson County travel package include?
Rental cars, hotels and flights, or any combination of the three — it's your choice. Whether you're visiting Dickinson County with the kids or travelling solo, there's a bundle to fit your budget and style. Once you've made your booking, why not add on one or two activities?
What should I know before booking a Dickinson County travel package?
A package can be easier on the credit card than separately booking everything you need for your adventure. For example, combine your flights, hotels and rental cars and save a tidy sum. No matter your holiday plans, there's bound to be a package that matches your budget.
Can I choose my airline with a Dickinson County Expedia holiday package?
With a holiday package, the choice is in your hands. Whether you'd prefer to fly to Dickinson County in business or coach, simply pick from the available airline options. Expedia has access to more than 550 airline partners globally.
If I'm not able to travel, can I cancel my Dickinson County holiday package?
Your situation can change in the blink of an eye, so yes, you can. You may be able to change or cancel your Dickinson County holiday package at no cost if you've booked in the last 24 hours. For older bookings, you can still make the necessary changes, but your hotel, car rental company or airline may impose a fee. Need more information? Check out our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.

* 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.