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Vacation Homes in Obrien County

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Top cities in Obrien County

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

Sheldon

Sheldon

Find vacation rentals that suit your style

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Apartments
Apartments
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Aparthotels

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Obrien County vacation homes

A kitchen with a marble countertop, two striped vases, and a dining area visible through a glass door.

1. Amazing West Lake Okoboji Home! Location, Location, Location!!!

Amazing West Lake Okoboji Home! Location, Location, Location!!!
Arnolds Park
9.8 out of 10, Exceptional, (211 reviews)
"Great location!"
United States
Linda N.
Amazing West Lake Okoboji Home! Location, Location, Location!!!
A wooden deck with outdoor furniture, a table, and chairs.

2. Family-Friendly Retreat on Julia Street - Explore Okoboji from Your Doorstep

Family-Friendly Retreat on Julia Street - Explore Okoboji from Your Doorstep
Okoboji
9.8 out of 10, Exceptional, (44 reviews)
"Smooth all around and a nice house for an affordable price"
United States
Trevor H.
Family-Friendly Retreat on Julia Street - Explore Okoboji from Your Doorstep
A living room with a sofa, armchair, coffee table, and a rug.

3. Roomy 4-bedroom home across the lake in Lake Park, IA. Sleeps 7

Roomy 4-bedroom home across the lake in Lake Park, IA. Sleeps 7
Lake Park
9.8 out of 10, Exceptional, (13 reviews)
"I like how easy was to check in the house was beautiful"
United States
Shirley M.
Roomy 4-bedroom home across the lake in Lake Park, IA. Sleeps 7
An indoor pool area with slides, a climbing net, and a water slide.

4. PRIME LOCATION AT BRIDGES BAY RESORT!!!

PRIME LOCATION AT BRIDGES BAY RESORT!!!
Arnolds Park
10.0 out of 10, Exceptional, (103 reviews)
"Great place to stay! "
United States
Stuart H.
PRIME LOCATION AT BRIDGES BAY RESORT!!!
An outdoor deck with two chairs and a table, surrounded by a wooden fence and a tree.

5. 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 AED 450
AED 771 total
includes taxes & fees
23 Nov - 24 Nov
Orange City Getaway • 2 King Suites • Garage • Coffee Bar
A modern kitchen with white cabinetry, a large island, stainless steel appliances, and a dining area in the background.

6. Elegant 5-bedroom house in Sioux Center near Dordt University and downtown.

Elegant 5-bedroom house in Sioux Center near Dordt University and downtown.
Sioux Center
10.0 out of 10, Exceptional, (20 reviews)
"A great property for our family!"
United States
Ivan S.
Elegant 5-bedroom house in Sioux Center near Dordt University and downtown.
A kitchen with a central island, wooden cabinets, and a dining area with a bench and chairs.

7. Large Family Home

Large Family Home
Milford
9.6 out of 10, Exceptional, (28 reviews)
"Very hospitable and friendly host. The perfect property for our large group!"
United States
Kirsten
Large Family Home
An indoor water park with slides, a play structure, and palm trees.

8. Lounge at the Lake with 6 waterpark passes! 50% off rate for 28 day min. stay.

Lounge at the Lake with 6 waterpark passes! 50% off rate for 28 day min. stay.
Arnolds Park
10.0 out of 10, Exceptional, (105 reviews)
"Great property. Loved the location with an open backyard and close to a pool. Hosts were great at communicating and place was clean. Only suggestion would be to add a few more blankets for use for beds in garage. Would definitely stay again!"
United States
Erica F.
Lounge at the Lake with 6 waterpark passes! 50% off rate for 28 day min. stay.
A deck area with string lights, outdoor furniture, and a small pool.

9. Cozy Lakeside Retreat with Beach Access, Scenic Views & Endless Amenities

Cozy Lakeside Retreat with Beach Access, Scenic Views & Endless Amenities
Spirit Lake
9.6 out of 10, Exceptional, (24 reviews)
"We love staying at the"
United States
Shaylyn W.
Cozy Lakeside Retreat with Beach Access, Scenic Views & Endless Amenities
A spacious living room with a fireplace, leather sofas, a coffee table, and a large sliding glass door leading to an outdoor area.

10. Millers Bay Canal Retreat

Millers Bay Canal Retreat
Milford
9.6 out of 10, Exceptional, (11 reviews)
"Host was great to work with. Plenty of room to spread out. We had a great stay!"
United States
Michelle
Millers Bay Canal Retreat
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 reviews in Obrien County

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

10/10 Excellent

Clean and comfortable bed. Enjoyed my stay.
United States
Noel
Reviewed October 25, 2026
Cobblestone Inn & Suites - Sheldon

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