
Holiday rentals in Oakland
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Top-rated holiday rentals in Oakland
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The Railhouse in Weston, Iowa
Completely renovated older 1880 home in a quaint little town in Weston, Iowa. Country setting with the view of farm fields, rolling hills, the ambiance of a slow moving train once a day or evening. A short paved walking/ bike trail, that soon will connect to another trail. There is a county highway out front that will have traffic. You can wake up to a beautiful view and enjoy your coffee on the deck or a walk in our back lot and listen to nature. We are across the river from Omaha, Nebraska.
4.99 out of 5 average rating, 83 reviews
Imogene Farmhouse/SunnySide Saloon
Lounge outside in the hammock and watch the cornstalks swaying in the breeze or the cattle grazing. Boardgames, cards, records, & fiber-optic wi-fi to keep you entertained when inside. A kitchenette/bar area to relax & rehash the day's adventures. Located one mile from Imogene, a small but mighty Irish community. Book a tour of the stunning St. Patrick Catholic Church on the hill, wet your whistle at the Emerald Isle Bar & Grill, or bike/walk through the tree-lined Wabash Trace Nature Trail.
4.96 out of 5 average rating, 156 reviews
Cozy Forest Refuge ( Accommodate 1-11) (7 Beds)
4 bedrooms, 2 1/2 bathrooms and 7 beds - its great for anyone. Master has King and private bath. With low price you can be an individual, couple, or up to 11 people. Fire pit, washer and dryer, WiFi, and parking space. It is a 1425 sq home tucked in Fontenelle forest, very peaceful and quiet. Within 15 minutes of The Old Market, Charles Schwab Field , and 10 minutes to the Henry Doorly Zoo! Great places to hike in the neighborhood. Great for individuals, couples, families, and big groups.
4.97 out of 5 average rating, 394 reviews
Cheerful two bedroom home in peaceful neighborhood
Relax with the whole family at this peaceful two bedroom home. Beautiful quiet neighborhood close to interstates, sports fields, IWCC, Henry Doorly Zoo, bike/running trails, downtown Omaha, Old Market, CHI Center, Eppley Airfield, and more. Spacious tree filled private backyard, outdoor patio, and grill. Plenty of parking. Great WiFi and Netflix, YouTube TV and Discovery+. Washer/dryer available. Dog friendly but no cats please. No gatherings, events, or parties inside or outdoors.
4.98 out of 5 average rating, 435 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.
4.98 out of 5 average rating, 252 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.
4.97 out of 5 average rating, 179 reviews
Mae & Mia’s Sweet Escape
Escape to this sweet, cozy cottage bursting with charm in the heart of Council Bluffs. Walking distance to historic downtown (100 Block) provides easy access to food, entertainment, and business. A 10-minute drive will get you to downtown Omaha for more amenities. The single bedroom and living room with pull-out bed will accommodate 4 travelers with room to spare if pets are traveling too! Fully fenced yard will keep them safe while offering ample space to run, fetch or relax.
5.0 out of 5 average rating, 123 reviews
Large Family Home
Enjoy our fully loaded home for holiday gatherings, working on the road, or just traveling by town. Includes a fully equipped kitchen, tvs with streaming, and washer/dryer. This is a four bedroom home. Three of the rooms have a queen bed, and the fourth room has a twin bed. Every room has a tv. The living room has a hide-a-bed sofa for extra places to sleep. We guarantee comforter and all are fresh when you arrive. Bathrooms and kitchen are fully sanitized as well. ❤️
4.91 out of 5 average rating, 96 reviews
Amber & Oak + Awesome Movie theater
🏡 Welcome to Amber & Oak, a cozy 3-bedroom Omaha home built for togetherness. The showstopper: a private home theater with a 100" TV with an amazing sound system, a plush oversized sofa, and everything you need to make popcorn, just hit play and settle in. Head to the basement games room for a ping pong table and a cozy daybed for extra downtime. Outside, gather around the fire pit or stretch out on the deck. Fully equipped kitchen, self check-in, and pet-friendly.
5.0 out of 5 average rating, 6 reviews
Boots, Class, come spread out and relax!
Come feel a slice of heaven nestled in the private surroundings of a historical farming backdrop. Watch the sunset from the barns, see the squirrels jumping in the trees and welcome the unforgettable sunrises right from your bedroom window. When you’re ready to live a day in the life… get dirty, pull up your boots, splash in the mud, play in the corn crib, use your imagination in the forests, dance in the rain, and most importantly, take pictures and make memories!
4.95 out of 5 average rating, 64 reviews
Fully Renovated, Luxurious unit awaits you!
Luxury Stay 10 Minutes from Downtown Omaha! Stay in a renovated industrial 2BR/1BA unit with modern amenities, including W/D. Explore Old Market’s cobblestone streets, top-rated restaurants, and Iowa museums. Enjoy scenic walks along the Missouri River and Heartland of America Park. Relax in a stylish, comfortable space perfect for work or leisure. Contact us for flexible stays. ✨ Book now for a perfect Iowa/Omaha getaway! ✨
4.95 out of 5 average rating, 115 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.
4.96 out of 5 average rating, 119 reviewsPopular amenities for Oakland holiday rentals
Other great holiday rentals in Oakland

Rare Find! Near Wedding Venues & Metro
4.96 out of 5 average rating, 46 reviews
Family Farmhouse
4.91 out of 5 average rating, 22 reviews
Lake home & pool 3 miles to CWS sleeps 12 8 beds
4.95 out of 5 average rating, 22 reviews
Harlan Hospitality House
4.95 out of 5 average rating, 65 reviews
Majestic VIEWS! FunAmenities & Best for Huge Group
4.85 out of 5 average rating, 55 reviews
Hunters Outpost 2 bedroom apt.
4.87 out of 5 average rating, 85 reviews
Quiet country setting in town.
5.0 out of 5 average rating, 93 reviews
Victorian Cottage steps from historic downtown
4.99 out of 5 average rating, 96 reviewsDestinations to explore
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