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, 102 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, 41 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.

Top Guest favourite
An open kitchen and living area features a large wooden dining table with seating for six. The modern kitchen includes dark cabinetry and stainless steel appliances. Natural light fills the space through a window above the sink, enhancing the clean lines and contemporary design.
Home in Jackson
5 out of 5 average rating, 65 reviews

Henderson Guest House: Modern Meets Cozy!

This beautiful and cozy newly constructed guest house is a perfect modern space for a single, family or group getaway! Sleeps 4 adults with king bedroom and ultra plush full queen sofa sleeper in living room , two electric fireplaces, two TVs, full kitchen, heated concrete floors and three blocks from downtown restaurants, shopping and walking trails and several areas parks. Furnished dining patio and seasonally available gas grill. No pets or parties please. All guests must be registered.

Guest favourite
A spacious living area features comfortable, reclining sofas arranged around a central table. Soft, gray carpeting is laid throughout the space, and natural light enters through a small window adorned with light curtains. Decorative elements include a wall shelf with small potted plants.
Home in Mountain Lake
5 out of 5 average rating, 15 reviews

9th Street Hideaway

Welcome to your cozy home away from home! This spacious and relaxing private basement suite offers the perfect blend of comfort and convenience. This space is perfect for couples, solo travelers, or business guests. Enjoy a private entrance, parking, and a quiet retreat featuring: -Queen bed -Additional queen air mattress available upon request -Dedicated office space -Fully equipped kitchenette -Bathroom with full shower -Gas fireplace -Smart TV & Wi-Fi -Shared deck access

Top Guest favourite
The cabin is displayed in a serene setting, featuring a spacious exterior with well-maintained green grass. A covered patio area with seating is visible, alongside a grill. Mature trees surround the building, contributing to the peaceful atmosphere.
Cabin in Terril
5 out of 5 average rating, 28 reviews

Hunters Paradise Cabin

This property is located in the perfect location for every hunter, fisherman and boater. We are on the North end of Trumble lake surrounded by thousands of acres of public hunting. We are only 5 miles from Lost Island and 20 miles to the Okoboji area. We have a heated garage for the pets to stay with some kennels provided. Pets are welcome to run the yard and play. No hunting is allowed on the property. There is 300 acres just across the creek to hunt.

Guest favourite
Home in Spencer
4.89 out of 5 average rating, 19 reviews

Hot Tub Hideaway

A peaceful haven close to everything, boasting a brand new saltwater hot tub on our expansive deck! Perfectly situated near Spencer & 20 minutes away from Okoboji, our 3 bedroom/2 bath home offers an unparalleled escape. Perfect for a family getaway or vacation with friends. Make unforgettable memories in our beautiful home complete with everything you need. There is plenty of space to park your boat if needed. We can also accommodate hunting doggos.

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, 52 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, 219 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, 344 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 out of 5 average rating, 10 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.

Guest favourite
A charming single-story home features a gabled roof and light-colored siding. A welcoming front door with a large window is approached by a short pathway bordered by neatly kept grass. Trees provide shade in the background, contributing to a peaceful setting.
Home in Windom
4.77 out of 5 average rating, 31 reviews

Little house with a cozy feel

Kick back and relax in this calm, stylish space. It offers all that you would get from a hotel space plus so much more. It has living room up stairs with open concept to the kitchen. Queen Bedroom on the same level and bathroom. Downstairs is another sit room for a quiet relaxing feel, same level is a single bedroom and bathroom with a shower.

Guest favourite
Guesthouse in Fairmont
4.95 out of 5 average rating, 37 reviews

Train Depot

Take it easy at this unique and tranquil getaway. This is a real train depot that was relocated from Truman, MN! This train depot retains much of its historical charm. Updates are ongoing to continue to make the Depot a luxurious stay without losing the history.

Popular amenities for Estherville holiday rentals

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