Dickinson County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Dickinson County Vacation

When the travel bug bites, book a vacation package to Dickinson County. Get ready to experience walking trails, views, hiking, and much more in this exciting destination. Not sure where to stay? Milford is among the leading cities to explore during a trip to Dickinson County. Start packing your bags, because your Dickinson County vacation is just a few clicks away with Expedia.

Top vacation destinations in Dickinson County

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Spirit Lake

Spirit Lake

Dickinson County Hotel Deals

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 CA $176 per night from Jul 12 to Jul 13
CA $176
CA $210 total
Jul 12 - Jul 13
includes taxes & fees
7.8/10 Good! (993 reviews)
"Pool was dirty and staff even came out, looked at it and never came back. No elevator which made it difficult to carry luggage up stairs."

Reviewed on Jun 28, 2026

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 CA $166 per night from Aug 3 to Aug 4
CA $166
CA $188 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (589 reviews)
"Great place. Excellent value and great location."

Reviewed on Jul 1, 2026

Vintage Block Inn & Suites
AmericInn by Wyndham Okoboji

AmericInn by Wyndham Okoboji

3 out of 5
1005 Brooks Park Dr Okoboji IA
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Aug 3 to Aug 4
CA $223
CA $245 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (625 reviews)
"Staff was very helpful and rooms were well maintained. Nice breakfast and long pool hours. Would stay here again."

Reviewed on Jun 29, 2026

AmericInn by Wyndham Okoboji
See all 445 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.
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Frequently asked questions

How much does a Dickinson County vacation 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 vacation 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 vacation?
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 traveling 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 vacation plans, there's bound to be a package that matches your budget.
Can I choose my airline with a Dickinson County Expedia vacation package?
With a vacation 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 vacation 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 vacation 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 wooden pier extending into calm water with a clear sky above.
Photo by KkelleyNC
Open Photo by KkelleyNC

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.
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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.