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Top cities in Obrien County

A river meandering through a green landscape with a marina and boats.
Vacation Rentals

Sheldon

Sheldon

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Obrien County holiday rentals

An outdoor deck with two chairs and a table, surrounded by a wooden fence and a tree.

1. Orange City Getaway • 2 King Suites • Garage • Coffee Bar

Orange City Getaway • 2 King Suites • Garage • Coffee Bar
Orange City
10.0 out of 10, Exceptional, (17 reviews)
"The accommodations were amazing. "
United States
Jessica R.
The price is £160
includes taxes & fees
10 Nov - 11 Nov
Orange City Getaway • 2 King Suites • Garage • Coffee Bar
A dining area with a long wooden table set for a meal, surrounded by chairs.

2. Raider Roost-Putting Green/Fire Pit/ Game Room Close to NWC & Downtown!

Raider Roost-Putting Green/Fire Pit/ Game Room Close to NWC & Downtown!
Orange City
10.0 out of 10, Exceptional, (11 reviews)
"This is the best home away from home we’ve ever stayed at! The hosts were extremely communicative and helpful and they thought of EVERYTHING. This adorable little home is stocked with everything you could possibly need. We loved our stay, thank you!"
United States
Carissa V.
The price is £249
includes taxes & fees
6 Nov - 7 Nov
Raider Roost-Putting Green/Fire Pit/ Game Room Close to NWC & Downtown!
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 £85
includes taxes & fees
10 Nov - 11 Nov
Located across the road of West Lake Okoboji. 8 beds. Room for parking trailers
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining table set for four.

4. Spacious 2BR Condo & Garage + Perfect for Families + Walk to Dordt & Siouxnami

Spacious 2BR Condo & Garage + Perfect for Families + Walk to Dordt & Siouxnami
Sioux Center
The price is £137
includes taxes & fees
10 Nov - 11 Nov
Spacious 2BR Condo & Garage + Perfect for Families + Walk to Dordt & Siouxnami
A compact kitchen with a microwave, refrigerator, and a small trash bin.

5. 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, (27 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 £110
includes taxes & fees
13 Nov - 14 Nov
2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps.
A modern bathroom with a toilet, sink, and shower.

6. Added a little Halloween Decor!<br>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

Added a little Halloween Decor!<br>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 £100
includes taxes & fees
14 Nov - 15 Nov
Added a little Halloween Decor!<br>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 modern living room with a leather sofa, striped armchairs, a white coffee table, and a red vintage refrigerator.

7. 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, (23 reviews)
"Very clean well cared for property, comfortable accommodations!"
United States
Cynthia M.
The price is £164
includes taxes & fees
10 Nov - 11 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 two-story house with a covered porch supported by white columns, a name plaque reading 'Two O Seven,' and a set of stone steps leading to the entrance.

8. Spacious 4 BDR Historic Home in Sioux Center

Spacious 4 BDR Historic Home in Sioux Center
Sioux Center
10.0 out of 10, Exceptional, (22 reviews)
"The house was beautiful! The space was perfect for us traveling with my parents and our children."
United States
Jayne B.
The price is £179
includes taxes & fees
10 Nov - 11 Nov
Spacious 4 BDR Historic Home in Sioux Center
A swimming pool with a slide, lounge chairs, and a small building.

9. 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 host, beautiful location, clean and comfortable."
United States
Jodie O.
The price is £293
includes taxes & fees
8 Nov - 9 Nov
Bridges Bay spacious, well-stocked kid-friendly home. 6 Pool Passes. Sleeps Ten
A modern bedroom with a grey sofa, a bed, and a TV mounted on the wall.

10. Artsy Tartsy Bunk House off West Lake Okoboji

Artsy Tartsy Bunk House off West Lake Okoboji
Arnolds Park
7.6 out of 10, Good, (10 reviews)
"Walking distance to many local attractions."
United States
Tracy F.
The price is £213
includes taxes & fees
8 Nov - 9 Nov
Artsy Tartsy Bunk House off West Lake Okoboji
A spacious kitchen with a central island, wooden flooring, and a view to a living area.

11. 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 £304
includes taxes & fees
12 Nov - 13 Nov
Cozy Condo by Boardwalk, Restaurants, Golf
A modern living room with a black leather sofa, yellow chairs, and a dining table.

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 £239
includes taxes & fees
8 Nov - 9 Nov
New!! 4 Bedroom Unit sleeps 14
A dining area with a wooden table, two chairs, a clock on the wall, and a window with curtains.

13. 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 £318
includes taxes & fees
6 Nov - 7 Nov
Just steps from The Green Space and Broadway Street. Fantastic Location for All the Fun!
A multi-story building with balconies overlooking a body of water.

14. 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)
"We had an amazing time, with great views. The condo had all the necessities and Janel was great to work with and very responsive. We hope to be back next year!"
United States
Deb E.
The price is £300
includes taxes & fees
9 Nov - 10 Nov
Bridges Bay Boji Lake-View Condo For Rent!!
A modern kitchen with a central island, a dining area with a black table, and a living room with a sofa and a coffee table.

15. 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 £310
includes taxes & fees
10 Nov - 11 Nov
Fantastic Yard and Fun Location In Arnolds Park. Walk to Everything!
A spacious living room with a sectional sofa, a ceiling fan, and a large window offering a view of the outside.

16. Bridges Bay Retreat - The Perfect Okoboji Getaway

Bridges Bay Retreat - The Perfect Okoboji Getaway
Arnolds Park
10.0 out of 10, Exceptional, (2 reviews)
"Great for the price, comfy and close to all the activities in Arnold’s park"
United States
Connor S.
The price is £278
includes taxes & fees
8 Nov - 9 Nov
Bridges Bay Retreat - The Perfect Okoboji Getaway
A modern living room with a grey sofa, a wooden coffee table, a flat-screen TV, and a fireplace.

17. Triboji Beach Club Cottage | Cozy West Okoboji Escape with Lake Access

Triboji Beach Club Cottage | Cozy West Okoboji Escape with Lake Access
Spirit Lake
8.8 out of 10, Excellent, (5 reviews)
"Wonderfully clean property with all the necessary amenities to make for a great, relaxing weekend. I highly recommend this property!"
United States
Kari S.
The price is £419
includes taxes & fees
16 Nov - 17 Nov
Triboji Beach Club Cottage | Cozy West Okoboji Escape with Lake Access
A swimming pool area with multiple slides and lounge chairs.

18. The Hook Wine and Sinker House at Bridges Bay Resort

The Hook Wine and Sinker House at Bridges Bay Resort
Arnolds Park
9.6 out of 10, Exceptional, (18 reviews)
"Great vacation and resort"
United States
Jennifer E.
The price is £355
includes taxes & fees
6 Nov - 7 Nov
The Hook Wine and Sinker House at Bridges Bay Resort
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

19. The Waterline Okoboji | Pool + Lake Access

The Waterline Okoboji | Pool + Lake Access
Okoboji
The price is £266
includes taxes & fees
8 Nov - 9 Nov
The Waterline Okoboji | Pool + Lake Access
A modern living room with a sofa, ottoman, and a dining area with bar stools.

20. The Stay Cabin is a part of the Stay Properties locations at 271 Hwy 71

The Stay Cabin is a part of the Stay Properties locations at 271 Hwy 71
Arnolds Park
10.0 out of 10, Exceptional, (16 reviews)
"Sherri is awesome to work with and always very accommodating. We make our annual trip to Iowa with our large family and the staycation cabin worked perfect for us."
United States
Kelli n.
The price is £351
includes taxes & fees
8 Nov - 9 Nov
The Stay Cabin is a part of the Stay Properties locations at 271 Hwy 71
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 Obrien County Hotel Reviews

A spacious indoor area with a stone fireplace, leather seating, and a projection screen on the wall.
Cobblestone Inn & Suites - Sheldon

Cobblestone Inn & Suites - Sheldon

Cobblestone Inn & Suites - Sheldon
Sheldon

8/10 Good

Clean room and pleasant hotel. Staff were friendly and helpful.
United Kingdom
Kay
Reviewed October 19, 2025
Cobblestone Inn & Suites - Sheldon

Find out more about Obrien County

Everything you need to know about Obrien 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 Obrien 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 Obrien County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Obrien County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Obrien 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 Obrien 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 Obrien County holiday rentals we have selected for you start as low as £82 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Obrien County rentals

At Expedia, we put the best Obrien 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 Obrien 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 Obrien 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 Obrien 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.

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