Holiday rentals in Bennington

Charming Guest Cottage

Take it easy at this unique and tranquil getaway. Maximum 2 guests - No guests UNDER the age of 12. A peaceful guest cottage located on the outskirts of Omaha and set on 2 acres that is shared by the owner’s 100 year old farmhouse and barn, you will relax and recharge at this charming cottage. The cottage is located down a short gravel lane shared by the owners. When it rains expect to walk through puddles. In the winter, if we have a heavy snow expect our shovels as soon as the day starts!

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.

Family friendly house/ SwimSpa

Heated 11 people swim spa pool available all year round. Enjoy at this charming, modern FAMILY-FRIENDLY home, conveniently located in a beautiful a quiet area. Located few minutes from shopping centers, Village pointe, and the Dodge expressway. Relax next to the fire place, at the furnished patio and the huge back yard or while watching TV. 2 bedrooms and 2 bathrooms located on the main floor. Additional bedroom and bathroom are in the basement. NO PARTIES as per Airbnb rules

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.

Willow Wood Wonder | Luxury Living | Insta Wall

⭐️Read my reviews!⭐️ Welcome to the Willow Wood Wonder! Located within this picturesque neighborhood, is this stylish, contemporary home ideal for families, or business travelers! Inside you’ll find multiple living areas, a gourmet kitchen, 4 generous bedrooms, ultra-modern bathrooms and a spacious yard with a decked patio, BBQ and outdoor lounge. You’ll be just minutes from Topgolf, the Zoo, museums & Downtown and only a 5 min walk to many restaurants all right on your doorstep.

Spacious Omaha Home | Pet-Friendly & Convenient

Spacious Omaha Retreat | Long-Stays Welcome Experience the perfect Omaha home-away-from-home! Whether you’re here for a weekend or a long-term stay, our sun-filled, pet-friendly space is ready for you. Location: 15 mins to the Zoo & Downtown; 5-10 mins to local dining/shopping. The Vibe: Modern, quiet, and spacious—perfect for families or remote work. Flexibility: Monthly stays available! Fully equipped for extended comfort. Book your short or long-term Midwest getaway today!

Modern Home in NW Omaha

BRING THE WHOLE CREW — NO SHARING BATHROOMS REQUIRED. This spotless, newly updated 3-bedroom, 3-bath home is built for families and groups who want space, comfort, and an easy stay. Every bedroom has its own bathroom, the beds are genuinely comfortable, and the quiet Northwest Omaha neighborhood keeps nights peaceful. Minutes from Village Pointe shopping, dining, and movies, with hosts who go above & beyond—families consistently give us 5-star reviews. Book with confidence.

Comfortable, 3-bedroom home on a quiet cul-de-sac

Welcome to a home away from home, conveniently located in the "backyard" of Omaha! All of our guests have full access to the entire home, located on a large corner lot in a quiet cul-de-sac. Less than 30 minutes from downtown (think Omaha Zoo, Century Link Center, etc.). Less than 20 minutes from I-80 and popular Omaha neighborhoods like Aksarben Village, and Midtown Crossing are only 15-20 minutes away. Only blocks away from some of the best restaurants around as well!

*Romantic* Rose Cottage with Hot Tub in Benson

Romantic Rose Cottage, north Benson. Minutes from UNMC, Downtown, CWS, CHI Center, Zoo, Dundee & Benson Restaurants. Beautifully designed space, perfect for short getaways and comfortable for long term stays . Wood floors, Essential cooking items, Breakfast nook with table for dining/work space. Off street parking 2 cars & 1 car garage suitable for a small car only. Washer & Dryer in basement. Furry family members welcome. Fully fenced back yard.

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.

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.

Warm & Welcoming Home

Newly remodeled and freshly furnished! Relax with the whole family or a group of friends at this comfortable home in West Omaha. Close to shopping, restaurants, coffee shops, golf courses, park, walking trail, and more, this home is a perfect place to unwind and recharge while away. Enjoy the spacious fenced back yard, deck and chairs. Exceptional neighborhood park nearby and toys for the kids in the garage.