Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

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Top Guest favourite
A sign reading 'Quirky Place' is prominently displayed against a light wood-paneled wall. Below the sign, a planter contains a variety of succulents, including a large cactus and smaller green plants, adding a touch of greenery to the entryway.
Place to stay in Omaha
4.94 out of 5 average rating, 209 reviews

Quirky Mid-Century Studio Near Omaha Favorites

Welcome to The Quirky Place a cozy, private Omaha studio with mid-century charm, modern touches, and personality. This comfortable space includes a Murphy bed with a super comfortable mattress, and a sofa bed, a 3/4 bath, fully stocked kitchen, driveway parking, space for up to 4 guests. Perfect for a quick getaway, work trip, concert, medical visit, family stay, or weekend get away. Cheerful, comfortable, a little unexpected, and easy to settle into...a bit more fun and a lot more interesting.

Top Guest favourite
Home in Benson
4.98 out of 5 average rating, 108 reviews

"Cozy Cottage" Getaway, Hot Tub & Fireplace Benson

Charming cottage nestled in Omaha's vibrant Benson neighborhood, near 60th & Manderson. 15 mins Downtown, Convention center, ball park, Zoo & Museums Perfect for a quiet getaway, romantic retreat or extended work stay with a mix of privacy & convenience. Fully equipped kitchen, modern bath, comfortable bed, easy to use gas fireplace (off during hot summer months) and Hot tub for 2 on private deck. Benson is known for it's live music, unique restaurants, craft breweries and local shops.

Top Guest favourite
The image captures a serene lake view during sunset, framed by silhouettes of trees. The calm water reflects soft hues of orange and blue, with scattered clouds adding texture to the sky. The setting sun is seen just above the horizon, creating a peaceful atmosphere.
Home in Council Bluffs
4.99 out of 5 average rating, 149 reviews

Cozy Lakeside Cottage for Families and Fun Seekers

Relax with the whole family at this peaceful lake cottage or take a needed solo getaway. Views of Lake Manawa and steps away you can put in your kayak or throw out a fishing line. Amazing trails nearby that connect to Wabash Trace, downtown Omaha, the Riverfront, and more. We had fun decorating the cottage with local art. Very close to I29 and I80, Iowa West Field House/Sports Plex, Iowa Western, Creighton, Henry Doorly Zoo, Lauritzen Gardens, Old Market, CHI Center, and so much more.

Top Guest favourite
Two repurposed grain bins are situated on a landscaped area, featuring a small patio with seating arrangements. A vibrant flower bed is placed adjacent to the patio, and a gravel pathway leads to the entrance. Lush greenery surrounds the structure, creating a serene environment.
Tiny home in Missouri Valley
4.98 out of 5 average rating, 248 reviews

Grain Bin Getaway

Nestled at the foot of the Loess Hills, this repurposed grain bin is a sight to see. Every inch of the inside has been customized for a relaxing and luxurious experience. Conveniently located just 30 minutes from downtown Omaha, as well as within a quick drive to numerous state parks. There is even an external electrical hook up for campers. Finally, our grain bin includes 20 acres of the Loess Hills to explore. We recommend hiking to the top of the ridge for sunset. It's breath taking.

Top Guest favourite
A rustic farmhouse is seen in the distance, surrounded by green fields and a neatly plowed crop area. A large barn and a silo are positioned on the property, with trees lining the background under a clear blue sky.
Farm stay in Glenwood
4.98 out of 5 average rating, 250 reviews

Ellington Place

A rustic farmhouse retreat on a crop producing farm, which means we could be planting or harvesting during your stay. Ellington Place has a furnished kitchen, updated bathroom and washer and dryer. Along with excellent outdoor entertainment, complete with a fire pit, porch for sitting and open area for short walks. The property is located 25 minutes from the Omaha metro area as well as less than 10 minutes from the Wabash Trace, a bike trail that travels through Mills County.

Guest favourite
A modern living area features a spacious gray sectional sofa and a round coffee table, with two blue accent chairs nearby. Large windows with black blinds allow natural light to illuminate the room. A ceiling fan adds comfort to the open layout.
Condo in Atlantic
4.97 out of 5 average rating, 175 reviews

2-bedroom, 1-bathroom whole apartment Atlantic, IA

Take in the sights and explore all that Atlantic, Iowa, has to offer when you stay in this brand-new, fully renovated 2-bedroom, 1-bathroom apartment located in the heart of downtown. It is on the second story of an iconic building called The Telegraph. You will have your own private entrance and access to the space with on-street parking available. The space comes with wi-fi, a roku, washer/dryer, top of the line kitchen appliances and an open concept great for entertaining.

Top Guest favourite
A bright living area presents large windows allowing natural light to fill the space. Comfortable teal sofas and a wooden coffee table create a casual atmosphere. A dark wood TV stand supports a flat-screen television, while a soft rug lies underneath, adding texture to the floor.
Guesthouse in Omaha
5 out of 5 average rating, 287 reviews

The Hidden Garden at Blackstone

Newly renovated second floor of a carriage house located on a historic property in the popular Blackstone District. Shares an acre of land with the main house, built in 1892 and occupied by the owners. Although situated in the middle of the city, the unit feels secluded from its urban environment and looks out onto a garden surrounded by trees, shrubs and flowers and is in walking distance to many restaurants and bars in both the Blackstone District and Midtown Crossing.

Top Guest favourite
A vibrant living area features contemporary furniture, including a leather sofa and multicolored chairs around a glass dining table. A striking abstract painting adds color to the wall, while natural light streams in from two window panes framed by light curtains.
Tiny home in Omaha
4.93 out of 5 average rating, 245 reviews

Contemporary Furnished Home

A cozy place with contemporary furnishing. A home away from home of your own with gated concrete driveway. Tennis court area welcomes you each day for your daily exercise. Full kitchen and laundry are among the amenities provided for your additional comfort. Grocery stores and restaurants are just minutes away to satisfy your cravings early morning or late nights. Multiple gas stations & churches are are just around the corner.

Top Guest favourite
An expansive living area features large windows that provide a view of the surrounding landscape. High ceilings are complemented by wooden beams. A comfortable seating area includes a dark sofa, and a foosball table is visible in the space, enhancing the recreational atmosphere.
Home in Omaha
4.96 out of 5 average rating, 113 reviews

Hangar 1 with a river view

Large secluded home with a private drive and an amazing view! This three bedroom, three full bath home with an aviation theme, has plenty of space with a view of the Missouri River and a hot tub off of the master. Three queen beds, a twin with a twin trundle, and a pull out couch can sleep up to 10. Foosball and air hockey tables. There is a bike path at the end of the driveway and only a 7 min drive to Eppley Airfield.

Guest favourite
The exterior of the Malvern Depot bunkhouse is shown, featuring a light-colored facade with green shutters and a welcoming red door. A bench sits outside, and a bicycle leans against the building. The paved Wabash Trace pathway runs alongside a grassy area.
Cabin in Malvern
4.9 out of 5 average rating, 291 reviews

Malvern Depot

A railroad depot renovated into a bunkhouse located midway on the Wabash Trace Nature Trail. It includes 2 bedrooms, kitchenette, and bathroom with shower. A/C & heat, coffee maker, dorm fridge, microwave, and toaster oven. Linens and towels provided. One queen bed, the other twin bunk beds. The Futon in the living area folds out. Conveniently located 2 blocks from downtown. No pets please.

Top Guest favourite
Barn in Oakland
5 out of 5 average rating, 25 reviews

The Great Country Escape - Grain Bin Stay

A SUPER UNIQUE STAY! THIS 45 YEAR OLD BIN HAS BEEN USED ON THE FAMILY FARM FOR YEARS UNTIL RECENTLY. WHEN IT BECAME TOO SMALL FOR TODAY'S FARM SIZE, WE HAD AN IDEA... THE BIN IS A MODERN OASIS IN THE MIDDLE OF A FIELD. OFF THE WHITE GRAVEL ROAD, YOU'LL REACH A SPOT OF TRANQUILITY WITH BIRDS CHIRPING, COWS MOOING AND THE OCCASIONAL NEIGHBOR WAVING AS THEY PASS BY.

Top Guest favourite
A charming guest cabin is nestled among lush greenery, featuring a welcoming porch with wooden steps leading to the entrance. Large windows allow natural light to fill the space, surrounded by trees that enhance the secluded atmosphere.
Cabin in Red Oak
5 out of 5 average rating, 63 reviews

Idlewood Cabin

Take it easy at this unique and tranquil getaway. Set on a wooded hillside overlooking the East Nishnabotna River valley, our lovely guest cabin is a great place to relax ( no TV in cabin ). Wake up in the morning to birdsong and the chatter of squirrels in the trees. Enjoy a campfire in the picnic area just outside your door. Just a note, we don't allow pets.

Popular amenities for Oakland holiday rentals