Holiday houses in Estherville

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Top-rated holiday rentals in Estherville

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A welcoming entrance features a covered porch with white railings and steps leading to a grassy area. Decorative plants are arranged alongside a pathway of stones and red mulch, enhancing the cottage's charming exterior.
Home in Spencer
4.91 out of 5 average rating, 105 reviews

Country Cottage 15 Mins from Okoboji

This spacious cottage is centrally located between Spencer and the lakes area, right off of Hwy 71. The upstairs loft features a queen, full and a single bed, desk, and closet and lots of space. The main level has a full kitchen with dining space, large living room with two couches and a TV, and a full bathroom with washer and dryer. This is a great place for long term stays as it offers your own private accommodations and off-street parking. Note: Due to allergies, No smoking inside, No pets.

Guest favourite
An inviting interior porch showcases a cozy seating area with four patterned chairs arranged around a small table. Natural light filters through multiple windows, illuminating a corner with cushions and a plant. A patterned rug adds warmth to the space.
Cabin in Spirit Lake
4.88 out of 5 average rating, 43 reviews

Lakefront Cabin | East Okoboji Lake | Private Dock

A historic lakefront cabin on East Okoboji Lake with a private dock, gas fire table, and sweeping lake views. Swim from the dock and wake up with a cup of coffee and the water right outside your door. Inside: a cozy bedroom, a sunlit porch overlooking the lake, a living room with a sleeper sofa, and a functional kitchen. The bike trail is right across the street. Whether you're celebrating an anniversary or simply overdue for a quiet lake weekend, this Okoboji cabin is your home away from home.

Guest favourite
A spacious living area features two brown leather sofas arranged around a decorative area rug. Exposed wooden beams adorn the ceiling, while natural light fills the room through large windows. Artwork is displayed on the walls, adding character to the inviting space.
Cabin in Okoboji
4.93 out of 5 average rating, 97 reviews

Okoboji Bunker House

Your family will be close to everything when you stay at this centrally-located place. This rustic cottage has a Western log cabin feel. The home is right across from East Lake Okoboji and is just walking distance to Barefoot Bar and Parks Marina! This spacious 4 bedrm/2 bath home offers laundry facilities, 4 queen beds, bicycles, outdoor wood-burning fireplace w/wood, natural gas grill, and most home furnishings including, but not limited to, pots, pans, silverware, toaster, coffee pot, etc!

Guest favourite
A fire pit with blue adirondack chairs is positioned on a grassy area near the lake. A wooden dock extends into the water, where boats are visible. The sunset creates a colorful sky, enhancing the serene lakeside atmosphere.
Home in Orleans
5.0 out of 5 average rating, 20 reviews

Lakefront Cabin on Big Spirit

Relax with family and friends at this peaceful cabin on Big Spirit Lake. Completely remodeled in 2023. Enjoy the open floor plan and beautiful outdoor space. This cabin is located on the south east side of Spirit Lake. A short walk to the spill way, boat ramp and park! A private dock and a swimmable beach is the perfect place to enjoy swimming, fishing and floating. Enjoy all the amenities of home including central air, full size washer and dryer, Blackstone grill, wifi and flat screen tv.

Top Guest favourite
A spacious living area is visible, featuring a comfortable seating arrangement with a sofa and recliners facing a modern fireplace. Large windows allow natural light, while a wooden table stands centrally. Decorative elements include a wall clock and unique art pieces, enhancing the room's character.
Cabin in Emmetsburg
4.97 out of 5 average rating, 62 reviews

Cabin / Shouse - Hot Tub - Mini Highland Cows!

Unwind just a mile from Emmetsburg on a hard-surfaced road. You’ll have a three-bedroom guesthouse and hot tub to yourself. Take in views of our miniature Highlands and enjoy the natural beauty of surrounding public hunting ground. Stroll along our private walking path or head to the Des Moines River trail for a peaceful walk. The guesthouse sits on the same property as our home but is positioned for privacy. Whether it's for outdoor adventure or a relaxing getaway, this is perfect.

Top Guest favourite
Farm stay in Spencer
4.97 out of 5 average rating, 284 reviews

The Bunkhouse at Hobby Horse Acres

Beautiful rural acreage with private "bunkhouse" located minutes from the Okoboji Iowa Great Lakes, Historic Spencer, and the Clay County Fair, the world's greatest county fair. Enjoy the peaceful setting including outdoor fire pit area, gazebo area, playground, barn with animals to pet, fruit trees, and room to roam. Full kitchen is included. Two private bedrooms and plenty of hang-out space and extra sleeping spaces.

Top Guest favourite
A spacious home is set amongst lush greenery, showcasing a large deck with patio furniture and shaded by trees. The well-maintained lawn extends around the property, offering a peaceful rural setting.
Home in Jackson
4.98 out of 5 average rating, 53 reviews

The Maple House

The Maple House is a spacious home with a large kitchen, dining room and living room. The laundry room is conveniently located in the front entry. A patio door in the living room leads to a large deck with patio furniture. Upstairs has a large open bedroom with three beds and a walk in closet. Country living close to all the action without the noise. Relax with the whole family at this peaceful place to stay.

Top Guest favourite
A cozy studio apartment features a comfortable gray couch paired with a small wooden table. The sleeping area includes a spacious bed with white linens, while natural light filters in through nearby windows. A soft area rug adds warmth to the wood-like flooring.
Loft in Fairmont
4.98 out of 5 average rating, 226 reviews

City of Lakes Loft

Newly constructed studio apartment above our garage. Calm, cozy and sunny interior in a quiet neighborhood setting. We have only lived in Fairmont a short time and we love it! It has a "Hallmark" town feel. You may meet our Labradoodle in the backyard - she is very friendly and will want to say Hi. We look forward to hosting you in this city of 5 Lakes! Cleaning fee included in the nightly rate.

Top Guest favourite
A rustic barn door painted in navy blue features welcoming text that reads 'Welcome to our Lake Retreat.' The door is situated in a hallway, and the adjacent wall is finished in a neutral color, contributing to the inviting atmosphere.
Apartment in Spirit Lake
4.9 out of 5 average rating, 355 reviews

Center Lake Retreat Entire Lower Level Walk Out

As ofJuly 1, 2021 we moved into this beautiful Lakeside home. The AIRBNB is NOT our entire home but it is the entire lower level which is our home. Gorgeous, private lakeside views. It is spacious with a private entrance if suitable, large kitchenette, family room, dining room, 2 bedrooms, bath/shower full bathroom. Lakeside access. There is complete privacy with a Barn Door closure.

Top Guest favourite
Cabin in Milford
5.0 out of 5 average rating, 13 reviews

Welcome to Camp Oz!

Step back in time at this retro vintage lake cabin. Nestled among the trees in Gull Point State Park, just steps from west lake Okoboji, this cabin is packed with personality and perfect for making memories—whether you’re gathered around the vintage barrel game table, whipping up breakfast in the retro kitchen, or sipping coffee on the sun-drenched porch.

Top Guest favourite
Cottage in Swea City
5.0 out of 5 average rating, 24 reviews

Aunt Martha’s Cottage -Pet Friendly

Welcome to Aunt Martha’s Cottage, a cozy retreat with the charm of yesteryear. Step into a simpler time, where the air is fresh, the pace is slow, and every corner holds warmth and nostalgia. With its cheerful kitchen and a bedroom dressed in soft quilts, this little cottage feels like home the moment you arrive.

Top Guest favourite
The exterior of a renovated blue farmhouse is shown, featuring a covered porch with seating. Lush green grass surrounds the cottage, with landscaped areas highlighted by flowers. Mature trees provide shade, and a gravel pathway guides the view toward the welcoming entrance.
Cottage in Spirit Lake
4.95 out of 5 average rating, 42 reviews

Grant’s Cottage on the Coyote Ranch

Just minutes from the attractions of the Iowa Great Lakes, Grant’s Cottage is a perfect getaway for families or couples! Enjoy the character and charm of the fully renovated 1874 farm house, the peaceful park-like setting, and all the modern amenities you’ll need for an Okoboji vacation.

Popular amenities for Estherville holiday rentals

  1. Airbnb
  2. United States
  3. Iowa
  4. Emmet County
  5. Estherville