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Holiday Rentals in Dickinson County

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An aerial view of a waterfront area with a Ferris wheel, a parking lot, and several boats docked at piers.
Vacation Rentals

Okoboji

Okoboji

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Dickinson County holiday rentals

Living area

1. Quiet 1 bedroom in Milford with King Bed

Quiet 1 bedroom in Milford with King Bed
Milford
9.8 out of 10, Exceptional, (134 reviews)
"Very clean property, host were very friendly and attentive. Really enjoyed our stay here and will definitely be back."
United States
Angela H.
The price is €109
includes taxes & fees
1 Dec - 2 Dec
Quiet 1 bedroom in Milford with King Bed
A modern bathroom with a wooden vanity, a large mirror, and a dark wooden door.

2. 2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps.

2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps.
Arnolds Park
10.0 out of 10, Exceptional, (28 reviews)
"We enjoyed our stay, great location and host. Loved that there was parking for our boat and trailer as well as plug ins. Highly recommend."
United States
AMY T.
The price is €133
includes taxes & fees
15 Nov - 16 Nov
2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps.
A two-story house with a front porch, a garage, and a deck.

3. 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, (41 reviews)
"Nice stay"
United States
Jennifer C.
The price is €103
includes taxes & fees
15 Nov - 16 Nov
Located across the road of West Lake Okoboji. 8 beds. Room for parking trailers
A wooden play structure with a lookout tower and slides, surrounded by a blue pool area.

4. 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. This suite is one the 2nd level and requires guest to use stairs

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. This suite is one the 2nd level and requires guest to use stairs
Arnolds Park
10.0 out of 10, Exceptional, (22 reviews)
"Just what we needed for our stay"
United States
Jeremiah M.
The price is €125
includes taxes & fees
22 Nov - 23 Nov
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. This suite is one the 2nd level and requires guest to use stairs
A compact living space with a kitchenette, a dining area, and a seating area.

5. Nautical 1BR Loft Steps to East Okoboji Park

Nautical 1BR Loft Steps to East Okoboji Park
Spirit Lake
The price is €248
includes taxes & fees
13 Nov - 14 Nov
Nautical 1BR Loft Steps to East Okoboji Park
A beach with people sunbathing and swimming, boats docked in the water, and a water tower in the background.

6. 1400 sf 3 bedrooms in Arnolds Park-King bed<br>This suite is on the 3rd floor and does require a guest to use the steps.

1400 sf 3 bedrooms in Arnolds Park-King bed<br>This suite is on the 3rd floor and does require a guest to use the steps.
Arnolds Park
10.0 out of 10, Exceptional, (24 reviews)
"Very clean well cared for property, comfortable accommodations!"
United States
Cynthia M.
The price is €199
includes taxes & fees
13 Nov - 14 Nov
1400 sf 3 bedrooms in Arnolds Park-King bed<br>This suite is on the 3rd floor and does require a guest to use the steps.
A swimming pool with a slide, lounge chairs, and a small building.

7. Bridges Bay spacious, well-stocked kid-friendly home. 6 Pool Passes. Sleeps Ten

Bridges Bay spacious, well-stocked kid-friendly home. 6 Pool Passes. Sleeps Ten
Arnolds Park
10.0 out of 10, Exceptional, (162 reviews)
"Great experience, great location"
United States
Andy M.
The price is €353
includes taxes & fees
15 Nov - 16 Nov
Bridges Bay spacious, well-stocked kid-friendly home. 6 Pool Passes. Sleeps Ten
A bedroom with a bed, a ceiling fan, a window with curtains, and a large mirror.

8. Perfect 2-bedroom house in Arnolds Park with great location.

Perfect 2-bedroom house in Arnolds Park with great location.
Arnolds Park
The price is €209
includes taxes & fees
25 Nov - 26 Nov
Perfect 2-bedroom house in Arnolds Park with great location.
A wooden pier extending into calm water with a sunset in the background.

9. Cozy Condo by Boardwalk, Restaurants, Golf

Cozy Condo by Boardwalk, Restaurants, Golf
Arnolds Park
9.8 out of 10, Exceptional, (26 reviews)
"Great location. Host responds very quickly and is super friendly. Great place to host the family"
United States
Josiah C.
The price is €365
includes taxes & fees
25 Nov - 26 Nov
Cozy Condo by Boardwalk, Restaurants, Golf
A beach with people sunbathing and swimming, a dock with boats, and a water tower in the background.

10. 2 Bedroom along Highway 71<br>This suite is on the 2nd level and requires guests to use stairs.

2 Bedroom along Highway 71<br>This suite is on the 2nd level and requires guests to use stairs.
Arnolds Park
9.2 out of 10, Wonderful, (23 reviews)
"Great location. Host was accommodating and helpful. "
United States
Christine R.
2 Bedroom along Highway 71<br>This suite is on the 2nd level and requires guests to use stairs.
A pool area with slides and a view of a building with balconies.

11. Bridges Bay Boji Lake-View Condo For Rent!!

Bridges Bay Boji Lake-View Condo For Rent!!
Arnolds Park
9.8 out of 10, Exceptional, (139 reviews)
"Great condo for our family of five. Plenty of space with lots of windows and a great view. Check in and check out processes were straight-forward, and our host provided plenty of timely communications to put at ease. Highly recommend."
United States
Andrew S.
The price is €363
includes taxes & fees
13 Nov - 14 Nov
Bridges Bay Boji Lake-View Condo For Rent!!
A beach with people sunbathing and swimming, a dock area with boats, and a water tower in the background.

12. New!! 4 Bedroom Unit sleeps 14

New!! 4 Bedroom Unit sleeps 14
Arnolds Park
10.0 out of 10, Exceptional, (25 reviews)
"Super cute and clean, great spot to hang out for weekend."
United States
Madeline H.
The price is €318
includes taxes & fees
25 Nov - 26 Nov
New!! 4 Bedroom Unit sleeps 14
A beach with people sunbathing and swimming, a dock with boats, and a water tower in the background.

13. Fantastic Location-Roof Top Patio (shared) and King Bed<br>This suite is on the 2nd level and requires guest to use stairs.

Fantastic Location-Roof Top Patio (shared) and King Bed<br>This suite is on the 2nd level and requires guest to use stairs.
Arnolds Park
10.0 out of 10, Exceptional, (37 reviews)
"Very nice and clean place. Great beds. I will stay there again."
United States
Patty F.
The price is €198
includes taxes & fees
6 Dec - 7 Dec
Fantastic Location-Roof Top Patio (shared) and King Bed<br>This suite is on the 2nd level and requires guest to use stairs.
A dining area with a wooden table, two chairs, a clock on the wall, and a window with curtains.

14. Just steps from The Green Space and Broadway Street. Fantastic Location for All the Fun!

Just steps from The Green Space and Broadway Street. Fantastic Location for All the Fun!
Arnolds Park
10.0 out of 10, Exceptional, (15 reviews)
"We had a great time at this air b n b for my bachelorette!! It was very spacious, close to the bars, and so cute for bachelorettes! I would stay here again and again"
United States
Kelsie H.
The price is €390
includes taxes & fees
25 Nov - 26 Nov
Just steps from The Green Space and Broadway Street. Fantastic Location for All the Fun!
A spacious living area with a large gray sofa, a kitchen with a bar, and large windows offering a view of the outdoors.

15. Haywards Bay Overlook

Haywards Bay Overlook
Okoboji
10.0 out of 10, Exceptional, (1 review)
"This property is beautifully situated on the lake front. We swam off the boat dock, ate breakfast on the deck and watched a lightning storm in the distance. Breathtaking views! Very clean and organized; all the beds were comfy with many choices of pillows. Two laundry rooms and numerous beach towels made it easy to enjoy the lake and Okoboji beaches. Great place for families with two full living room spaces! We did not use the second house because our group was smaller. We used the message host...
United States
Claudia B.
The price is €2,422
includes taxes & fees
25 Nov - 26 Nov
Haywards Bay Overlook
A modern kitchen with stainless steel appliances, a bar area, and wooden flooring.

16. Charming remodeled 4-Bedroom home with fire pit

Charming remodeled 4-Bedroom home with fire pit
Spirit Lake
10.0 out of 10, Exceptional, (25 reviews)
"Great place, only down side was traffic noise as it is just off of the main road, but it was not a big deal at all."
United States
Becca D.
The price is €366
includes taxes & fees
16 Nov - 17 Nov
Charming remodeled 4-Bedroom home with fire pit
A beach with people sunbathing and swimming, boats docked in the water, and a water tower in the background.

17. Fantastic Yard and Fun Location In Arnolds Park. Walk to Everything!

Fantastic Yard and Fun Location In Arnolds Park. Walk to Everything!
Arnolds Park
10.0 out of 10, Exceptional, (33 reviews)
"Very nice property. Friendly owners. Enjoyed our family time in Okoboji."
United States
Gwen
The price is €377
includes taxes & fees
18 Nov - 19 Nov
Fantastic Yard and Fun Location In Arnolds Park. Walk to Everything!
A living room with a grey sofa, a blue armchair, a floor lamp, and a patterned rug.

18. 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, (108 reviews)
"Great place to stay! Everything we needed plus a great bed. Parking for the boat and not far to state boat ramp"
United States
Jim S.
The price is €109
includes taxes & fees
1 Dec - 2 Dec
Quick 5-min drive to West Lake from Milford
A swimming pool area with multiple slides, lounge chairs, and a view of a lake.

19. Lake Front Condo on East Lake Okoboji in Bridges Bay Resort.

Lake Front Condo on East Lake Okoboji in Bridges Bay Resort.
ARNOLDS PARK
9.8 out of 10, Exceptional, (81 reviews)
"Great place to stay. Clean and spacious. Exactly as advertised!"
United States
Joshua F.
The price is €481
includes taxes & fees
15 Nov - 16 Nov
Lake Front Condo on East Lake Okoboji in Bridges Bay Resort.
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

20. The Waterline Okoboji | Pool + Lake Access

The Waterline Okoboji | Pool + Lake Access
Okoboji
The Waterline Okoboji | Pool + Lake Access
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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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, apart-hotels, 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 favorite 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 depends 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 selected for you start as low as €102 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.