Dickinson County Holiday Rentals

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Top Cities in Dickinson County

Our top choices for Dickinson County holiday rentals

Fantastic Location-Roof Top Patio (shared) and King Bed

Fantastic Location-Roof Top Patio (shared) and King Bed
2.0 star property
Arnolds Park
10.0 out of 10, Exceptional, (21)
"Nice place for family time"
United States
Cheryl Groen G.
The price is AU$304
includes taxes & fees
1 Jan - 2 Jan 2026
Fantastic Location-Roof Top Patio (shared) and King Bed

2 bedrooms with queen beds.

2 bedrooms with queen beds.
2.0 star property
Arnolds Park
10.0 out of 10, Exceptional, (16)
"It was very quite & clean! Perfect for our 2 night stay. "
United States
Michelle
The price is AU$224
includes taxes & fees
31 Dec - 1 Jan 2026
2 bedrooms with queen beds.

2 Bedroom along Highway 71

2 Bedroom along Highway 71
2.0 star property
Arnolds Park
9.2 out of 10, Wonderful, (20)
"Very clean, cute, well stocked apartment in a great location. Walkable to most Boji activities. Will definitely stay there again. "
United States
Debra W.
The price is AU$230
includes taxes & fees
8 Jan - 9 Jan 2026
2 Bedroom along Highway 71

Cozy 2-bedroom suite with full kitchen, living room (couch, 2 chairs), dining table (2 stools), smart TV with cable. Perfect for short or long stays.

Cozy 2-bedroom suite with full kitchen, living room (couch, 2 chairs), dining table (2 stools), smart TV with cable. Perfect for short or long stays.
Arnolds Park
10.0 out of 10, Exceptional, (23)
"Convenient check in/check out process, really nice suite and a good location. We would recommend to any one looking for somewhere to stay in the Okoboji area!"
United States
CherylB
The price is AU$266
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy 2-bedroom suite with full kitchen, living room (couch, 2 chairs), dining table (2 stools), smart TV with cable. Perfect for short or long stays.

1 Bedroom Suite-Stay Suites-Hwy 71 Arnolds Park

1 Bedroom Suite-Stay Suites-Hwy 71 Arnolds Park
Arnolds Park
9.6 out of 10, Exceptional, (20)
"My favorite place to stay in Boji, Sherri is the best!"
United States
Shell D.
The price is AU$222
includes taxes & fees
31 Dec - 1 Jan 2026
1 Bedroom Suite-Stay Suites-Hwy 71 Arnolds Park

West Lake Okoboji Scout Cottage

West Lake Okoboji Scout Cottage
Arnolds Park
9.6 out of 10, Exceptional, (10)
"Nice clean cottage style. perfect for a couples stay. location is perfect for walking distance to many attractions including arnold's park and much more!"
United States
Stephanie K.
The price is AU$726
includes taxes & fees
31 Dec - 1 Jan 2026
West Lake Okoboji Scout Cottage

Cozy Condo by Boardwalk, Restaurants, Golf

Cozy Condo by Boardwalk, Restaurants, Golf
Arnolds Park
9.8 out of 10, Exceptional, (19)
"Great location. Very nice place to stay. "
United States
Lewis S.
The price is AU$550
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy Condo by Boardwalk, Restaurants, Golf

Penthouse Luxury with Lake Views & 6 FREE waterpark passes daily at Bridges Bay.

Penthouse Luxury with Lake Views & 6 FREE waterpark passes daily at Bridges Bay.
Arnolds Park
9.8 out of 10, Exceptional, (81)
"this was the perfect spot for our family while we were in town for a wedding. The hosts were easy to work with and the property was comfortable and clean. "
United States
Katie W.
The price is AU$740
includes taxes & fees
31 Dec - 1 Jan 2026
Penthouse Luxury with Lake Views & 6 FREE waterpark passes daily at Bridges Bay.

Located across the road of West Lake Okoboji. 8 beds. Room for parking trailers

Located across the road of West Lake Okoboji. 8 beds. Room for parking trailers
Okoboji
9.6 out of 10, Exceptional, (25)
"Beautiful place , clean comfortable and quiet "
United States
Jeremy M.
The price is AU$216
includes taxes & fees
8 Jan - 9 Jan 2026
Located across the road of West Lake Okoboji. 8 beds. Room for parking trailers

Arnolds Park Iowa Street Funhouse at the Lake

Arnolds Park Iowa Street Funhouse at the Lake
Arnolds Park
8.4 out of 10, Very good, (5)
"Overall great place to stay!"
United States
Dawn K.
The price is AU$913
includes taxes & fees
8 Jan - 9 Jan 2026
Arnolds Park Iowa Street Funhouse at the Lake

The Fireside Fun Cabin at Bridges Bay Resort

The Fireside Fun Cabin at Bridges Bay Resort
Arnolds Park
8.6 out of 10, Excellent, (4)
"We had a great time"
United States
Caroline B.
The price is AU$743
includes taxes & fees
31 Dec - 1 Jan 2026
The Fireside Fun Cabin at Bridges Bay Resort

Lake view condo! Updated unit with 8 beds and 6 waterpark passes at Bridges Bay.

Lake view condo! Updated unit with 8 beds and 6 waterpark passes at Bridges Bay.
Arnolds Park
10.0 out of 10, Exceptional, (167)
"Great stay! Beautiful condo with gorgeous view! Walking distance (about a mile) to plenty of activities. "
United States
Teresa L.
The price is AU$664
includes taxes & fees
31 Dec - 1 Jan 2026
Lake view condo! Updated unit with 8 beds and 6 waterpark passes at Bridges Bay.

Bridges Bay Ranch style, single story home with 3 bedrooms and 2 bathrooms

Bridges Bay Ranch style, single story home with 3 bedrooms and 2 bathrooms
Arnolds Park
10.0 out of 10, Exceptional, (94)
"One of the best properties we have stayed at in Bridges Bay. Lisa did a great job with this one."
United States
Cale P.
The price is AU$795
includes taxes & fees
1 Jan - 2 Jan 2026
Bridges Bay Ranch style, single story home with 3 bedrooms and 2 bathrooms

The Monarch Cove House off West Lake Okoboji

The Monarch Cove House off West Lake Okoboji
Spirit Lake
10.0 out of 10, Exceptional, (1)
"Great property - quiet, clean and excellent location."
United States
Erin Z.
The price is AU$874
includes taxes & fees
31 Dec - 1 Jan 2026
The Monarch Cove House off West Lake Okoboji

Okoboji Oasis at the Lake in Arnolds Park

Okoboji Oasis at the Lake in Arnolds Park
Arnolds Park
9.6 out of 10, Exceptional, (5)
"Great location. Very close to Arnolds Park"
United States
Tom D.
The price is AU$997
includes taxes & fees
31 Dec - 1 Jan 2026
Okoboji Oasis at the Lake in Arnolds Park

The Hook Wine and Sinker House at Bridges Bay Resort

The Hook Wine and Sinker House at Bridges Bay Resort
Arnolds Park
9.8 out of 10, Exceptional, (12)
"Great house & great location! We really enjoyed our stay & will be back next year."
United States
Angie S.
The price is AU$701
includes taxes & fees
31 Dec - 1 Jan 2026
The Hook Wine and Sinker House at Bridges Bay Resort

Quick 5-min drive to West Lake from Milford

Quick 5-min drive to West Lake from Milford
Milford
9.8 out of 10, Exceptional, (84)
"Great place, great price, was quiet and good location "
United States
Ninja J.
The price is AU$187
includes taxes & fees
31 Dec - 1 Jan 2026
Quick 5-min drive to West Lake from Milford

Grassy Knoll Retreat on the Big Spirit Lake

Grassy Knoll Retreat on the Big Spirit Lake
Spirit Lake
10.0 out of 10, Exceptional, (10)
"Check-in was seamless and everything was very well stocked and organized. "
United States
Kevin L.
The price is AU$1,278
includes taxes & fees
4 Jan - 5 Jan 2026
Grassy Knoll Retreat on the Big Spirit Lake

Spacious Waterfront Corner Condo at Bridges Bay with 6 daily waterpark passes.

Spacious Waterfront Corner Condo at Bridges Bay with 6 daily waterpark passes.
2.0 star property
Arnolds Park
9.8 out of 10, Exceptional, (23)
"Lovely place with an amazing view! "
United States
Rebecca S.
The price is AU$858
includes taxes & fees
31 Dec - 1 Jan 2026
Spacious Waterfront Corner Condo at Bridges Bay with 6 daily waterpark passes.

Second Chances at the Lake | CentralPark D21 | Amusement Park Day Passes

Second Chances at the Lake | CentralPark D21 | Amusement Park Day Passes
Arnolds Park
10.0 out of 10, Exceptional, (1)
"Golf course view was beautiful & we walked across street to cool lake overlook bar with live music a few times."
United States
Renee B.
The price is AU$919
includes taxes & fees
31 Dec - 1 Jan 2026
Second Chances at the Lake | CentralPark D21 | Amusement Park Day Passes
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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Top Dickinson County Hotel Reviews

Find out more about Dickinson County

Everything you need to know about Dickinson County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Dickinson County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Dickinson County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Dickinson County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dickinson County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dickinson County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Dickinson County holiday rentals we have chosen for you start as low as AU$190 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Dickinson County rentals

At Expedia, we put the best Dickinson County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Dickinson County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Dickinson County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Dickinson County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.