Holiday houses in Bennington

Rainwood Cottage in the trees near the lake.

Take it easy at this unique and tranquil getaway, what was once a barn has been transformed into a 4 bed, 2 bath, 1850 sf Cottage nestled in an 8 acre grove of trees surrounded by 80 acres of farm ground. Only a couple of neighbors. This is truly a relaxing and unique place. Most of the ceilings and closets are lined with Red Cedar from Eastern Nebraska. Lake Cunningham is 1/2 mile to the east offering Bike trails, walking trails, 18 hole disc golf course, kayaking, paddle boarding and fishing .

Location · Family · Hospitality

Tranquility Retreat - NW Omaha family wedding HQ

Crafted with the whole family in mind, make Tranquility Retreat your Homaha away from home. Enjoy the cleanliness and comfort of this new-construction home. Just minutes from many major amenities in NW Omaha, Tranquility Retreat can be your getaway for sports, weddings, and events for you and your whole family. This home has been custom-designed for fun and comfort with vibrant colors, layout, and premium amenities. Make this the better alternative to the same old accommodations in Omaha.

Family · Location · Kitchen

Central Omaha Lux - Close to everything w/King bed

Indulge in modern comfort in the heart of it all a this Omaha retreat! This professionally designed and spacious home features 4 large bedrooms, 3 bathrooms, and secure garage parking. Sleek finishes and an open‑concept layout create a perfect style ideal for families or groups. Located just minutes from dining, shopping, and entertainment, you’ll enjoy both convenience and luxury. Whether you’re traveling with family, colleagues, or friends, this haven has everything you need for a great stay

Value · Family · Cleanliness

Private Waterfront Lake House | Near Omaha

Modern lakefront retreat in Valley, minutes from Omaha, the Elkhorn Athletic Association, DC West, and wedding venues such as Countryside and A View West Shores, plus Village Pointe. Located on a peaceful no-wake lake, this home features open living, water views, a king suite, queen bedroom, full-over-full bunk room, and loft sleeping area. Ideal for weddings, tournaments, school events, and weekend getaways. Enjoy sunset views and a relaxing lakeside setting with direct backyard lake access.

Family · Location · Hospitality

4br 3ba Ranch West Omaha Game Room Near splash prk

Large Ranch 4BR, 3full BA in Elkhorn West Omaha Near Splash pad and Park This remodeled home has a bright and inviting atmosphere, ideal for Multiple families or groups seeking a fully loaded home. Nestled in a safe, quiet neighborhood just steps from a splash park and playground, this home is designed for unforgettable memories. It's also only 1 mile from Flanagan fishing lake and scenic walking/running trail. 2 miles from Walmart, Target and Costco. Close to many restaurants and bars!

Location · Family · Backyard

Blue Diamond Dream.

This home is very spacious, sleeps 17 people at once comfortably, fantastic neighborhood & a fun place for both kids & adults. It's definitely designed to fit the needs of multiple families at the same time. The master Suite is on the main floor. This home accepts pets, children, & anyone with good intention. 2 full kitchens, gas stove on main & electric stove downstairs. Convenience stores are nearby such as Cassey gas station, Valentino's pizza, Runza resturant, Nail shop, & Subway.

Location · Family · Outdoor spaces

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.

Value · Family · Bathroom

​Spacious Omaha Getaway | Pet-Friendly & Central

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!

Value · Family · Layout

Spacious with Style 5BR Home, Hot Tub & Games!

Enjoy the perfect blend of relaxation and adventure at this spacious Omaha getaway! Designed for families and groups, there’s plenty of room to gather and unwind. The Zoo and Downtown are about 25 minutes away, with the airport 30 minutes away. Enjoy the year-round hot tub, three-car garage, and games for all ages. Pet-friendly and comfortable, this retreat is ready for your next memorable stay! *Pool is not heated and opens mid-May through September 4, 2026*

Location · Value · Outdoor spaces

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. Need an early check-in? Just ask and we'll do our best to make it happen! Minutes from Village Pointe shopping, dining, and movies, with hosts who go above & beyond—families consistently give us 5-star reviews. Book with confidence.

Value · Location · Access

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.

Family · Location · Bathroom

OmaStay| 25 Min to Zoo & Downtown| Kids Playground

Welcome to OmaStay, your cozy home in Omaha! Just 30 minutes from Downtown and the famous Henry Doorly Zoo, our home is perfectly located for families and travelers. Enjoy easy access to Standing Bear Lake and nearby parks and playgrounds for kids. Relax in a quiet, welcoming space after a day of exploring. Whether you’re here for fun or a peaceful getaway, OmaStay is the perfect place to create lasting memories.

Location · Family · Getting around