Dickinson County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Erik Rowley

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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

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

FlightsFlightsHotelsHotels

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 $107 per night from Feb 11 to Feb 12
CA $107
CA $128 total
Feb 11 - Feb 12
includes taxes & fees
7.8/10 Good! (909 reviews)
Room was clean, staff was attentive and polite. Breakfast was pretty good.

Reviewed on Dec 30, 2025

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 CA $125 per night from Feb 16 to Feb 17
CA $125
CA $149 total
Feb 16 - Feb 17
includes taxes & fees
7.6/10 Good! (644 reviews)
The room was very clean. The staff was very friendly and courteous.

Reviewed on Nov 13, 2025

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 CA $114 per night from Feb 11 to Feb 12
CA $114
CA $125 total
Feb 11 - Feb 12
includes taxes & fees
8.8/10 Excellent! (581 reviews)
The hotel staff was very nice! The room was beautiful; it was a much-needed getaway for me. Thank you!

Reviewed on Jan 27, 2026

AmericInn by Wyndham Okoboji
See all 415 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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