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Holiday houses in Cherokee

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Top-rated holiday rentals in Cherokee

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

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Top Guest favourite
A pathway lined with trees leads to a tranquil lake, where a warm sunset casts colors across the sky. A tower structure stands beside the water, illuminated by the fading sun, creating a serene lakeside setting.
Apartment in Storm Lake
4.98 out of 5 average rating, 64 reviews

Condo by the lake

This unit is perfect for summer and winter activities! Beautiful Lake and golf course views. Gorgeous sunsets. Newly built, two bedroom two bathroom condo. 3 minute Walking distance to Kings Point Resort, with beach access. Golf course directly next-door. Bike and walking trails with picnic areas across the street and around the lake. A 1 minute walk. Very popular lake for summer fishing and ice fishing. On site gym and recreational area. Indoor and outdoor shared Commons area with grill

Guest favourite
A comfortable living area is presented with a soft blue sofa adorned with a decorative pillow. A brown ottoman sits centrally, complemented by blue side tables. Warm light emanates from a floor lamp, while a patterned curtain softly filters natural light.
Home in Sheldon
4.9 out of 5 average rating, 196 reviews

East Windmill Large country farmhouse SheldonIA

Welcome to the cozy and rustic big farm house! Walk in to an inviting scene with everything you need including fridge, microwave, coffee pot, dishes, washer & dryer, TV and more. In the fridge you will find farm fresh eggs & coffee! You’ll be pleasantly surprised with the unique decor and original wood floors. Enjoy the views of the sunrise on the pasture with a few beautiful grazing cow calf pairs. It is a perfect place for a peaceful escape in the country on a real working farm.

Guest favourite
A wide view of Storm Lake stretches across the image, reflecting clear blue skies. Trees line the shore, providing a serene backdrop to residential homes in the foreground. The tranquil water surface mirrors the calm atmosphere, suggesting a peaceful retreat on the lake.
Home in Storm Lake
4.93 out of 5 average rating, 28 reviews

Inviting lakefront house!

Welcome to your perfect getaway on the serene south side of Storm Lake! Nestled on a quiet street, this beautifully maintained 3-bedroom, 2-bathroom home offers the ideal blend of comfort, charm, and breathtaking lake views. The newly remodeled kitchen is fully equipped for culinary adventures and offers picturesque views. Just beyond the kitchen, step through sliding glass doors into the sunroom, which has soaring windows that frame sweeping, panoramic views of Storm Lake.

Guest favourite
Home in Spencer
4.9 out of 5 average rating, 21 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.

Guest favourite
The exterior of the Red Tail Resort Cabin is shown, featuring a welcoming entrance with wooden accents. A spacious driveway leads to a two-car garage. The landscape is simple, with trimmed shrubs and grass, all set against a muted sky.
Home in Cherokee
4.79 out of 5 average rating, 14 reviews

Red Tail Resort

Escape to the tranquil Red Tail Resort Cabin in NW Iowa, a perfect getaway for a peaceful weekend or extended stay. Nestled on private land near a wildlife habitat, enjoy serene views and the beauty of nature. The cabin offers rustic charm with enough luxury to feel comfortable. Relax on the expansive covered deck overlooking a soon-to-be large lake. Additional living space is available in the lower level for friends or family—just ask the super host!

Guest favourite
The exterior of Bill's Cabin is shown, featuring a circular structure with corrugated metal siding. A covered patio is accessible through a central door, framed by greenery. A balcony extends above, offering views of the surroundings, while well-kept grass and landscaping enhance the entrance.
Barn in Primghar
4.94 out of 5 average rating, 35 reviews

Bill's Cabin

If you're looking to put a little farm in your city recreation, you might want to consider staying at Bill's Cabin, and play a few rounds at the Primghar Golf and Country Club. This "condo-cabin" complete with bar, stove, mini fridge and microwave downstairs, as well as a queen sized bed, fold-down futon and bathroom with shower upstairs. If you enjoy views, consider relaxing on Heckler's Deck which overlooks the 155 yard, par 3, Hole 8.

Top Guest favourite
Home in Orange City
5 out of 5 average rating, 17 reviews

Amsterdam Abode-King Beds-Garage- Coffee Bar!

Relax in this spacious 2-bedroom, 2-bath home featuring two king beds, an attached garage, a fully equipped kitchen, and a private deck. Located on a quiet cul-de-sac just minutes from Northwestern College and downtown Orange City, it's perfect for families, business travelers, and weekend getaways. Our well-behaved nephew rents the basement apartment with a separate entrance. Flexible check in options and an 11am check out.

Guest favourite
A modern kitchen features a central quartz island with seating for four. Stainless steel appliances are positioned against a backdrop of a marble-patterned wall. Wooden shelves display plants and kitchenware, while exposed brick adds character to the space. Original hardwood flooring complements the design.
Apartment in Remsen
4.92 out of 5 average rating, 12 reviews

The Block Studio-102

Spend your stay in a little history at The Block. Built in 1911 by John Groth, this studio apartment has elements of the original John Deere and later Ford factory including the original hardwood flooring, brick wall, and high ceilings. Most of the furnishings are comprised of reclaimed lumber from the dismantled car elevator. Historic photos of the building are throughout the common hallways for a trip back in time.

Guest favourite
A light grey sideboard is situated against a warm beige wall, topped with decorative items. A mirror reflects soft light from a lamp on one side, while a pair of candles and potted greenery balance the arrangement. A framed photo and a wooden rack adorn the surface.
Home in Marcus
4.94 out of 5 average rating, 106 reviews

The Sanctuary, a historic vacation rental

This beautifully remodeled and fully furnished rental (3 bedroom/ 2 bath—sleeps up to 6 adults) offers all of the comforts of home (+Wifi). Walking distance to grocery store, shops, dining, park and pool. Perfect for families and entertaining. Please respect no animals (severe allergies), smoking, parties or “booking for someone else” policies outlined in the house rules. If smoking outside, please use ashtray.

Top Guest favourite
A bright living area is furnished with two light-colored sofas adorned with decorative pillows. A dark wooden coffee table is positioned in front, complemented by a textured area rug. A wall-mounted television is visible, and natural light filters through a window with dark blinds.
Home in Ida Grove
4.9 out of 5 average rating, 157 reviews

Cozy like home! Fully Furnished

Experience the feeling of home in this warm and cozy 2-bedroom rental. With accommodations for up to 4 people, in a quiet neighborhood close to downtown Ida Grove. Relax or visit all our Castletown has to offer. You will be close to a movie theater, bowling alley, skating rink and local shopping. Also you will have a 7 mile walking trail that can take you out to beautiful Moorehead Park.

Top Guest favourite
An open-concept living area is visible, featuring large windows that allow natural light to brighten the space. A mix of seating options is arranged around a plush area rug. A colorful piece of wall art adds a unique touch to the room's neutral tones.
Loft in Cherokee
4.99 out of 5 average rating, 181 reviews

Library Loft Apartment - Left Wing

Located on the second level on West Main Street in historic downtown Cherokee, Iowa. This open-concept loft apartment is housed in an 1888 building and features a beautifully restored 10' x 10' skylight, French Empire chandeliers, 12' tin ceiling, and a balcony. Guests will enjoy numerous amenities, a splendid downtown view, restaurants and shopping.

Top Guest favourite
A welcoming living area is presented, featuring a cozy fireplace surrounded by a brick facade. Comfortable seating options are arranged around a central coffee table. A bookshelf filled with books and greenery adds a touch of life, while soft lighting creates an inviting ambiance.
Home in Alton
4.96 out of 5 average rating, 52 reviews

10th Hole Haven

Located on a historic golf course (Sioux Golf & Country Club) that was established in 1888. This 2 bedroom, 2 bathroom house sports a spacious living area including an 800 square foot deck that overlooks the golf course. Relax with the whole family, enjoy the fireplace in the winter, and the golf course views throughout the year.

Popular amenities for Cherokee holiday rentals