Dickinson County Holidays

Photo by Erik Rowley

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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$135 per night from 27 Nov to 28 Nov
S$135
27 Nov - 28 Nov
includes taxes & fees
Lake Okoboji Resort & Conference Center
Vintage Block Inn & Suites

Vintage Block Inn & Suites

2.5 out of 5
1107 Sanborn Ave Okoboji IA
The price is S$145 per night from 31 Oct to 1 Nov
S$145
31 Oct - 1 Nov
includes taxes & fees
Vintage Block Inn & Suites
Okoboji Inn & Suites

Okoboji Inn & Suites

2.5 out of 5
3400 Okoboji Ave Milford IA
Fully refundableReserve now, pay when you stay
The price is S$115 per night from 8 Nov to 9 Nov
S$115
8 Nov - 9 Nov
includes taxes & fees
9.2/10 Wonderful! (603 reviews)
"Everything was great. Will definitely stay again."

Reviewed on 25 Oct, 2026

Okoboji Inn & Suites
See all 449 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.

Stay near popular Dickinson County attractions

A girl standing in front of a store with a sign that reads "The Funhouse."

Arnolds Park

9.4/10 (357 reviews)
Explore the great outdoors at Arnolds Park, a lovely green space in Arnolds Park. Wander the lakeside in this family-friendly area.
See properties

* 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.