Holiday rentals in Bennington

Stunning 5BR Villa, Large Hot Tub & Scenic Yard!

Step into this stylish and spacious retreat, crafted for relaxation and fun! With 5 bedrooms, 3.5 bathrooms, and endless entertainment like a pool table and board games, it’s ideal for families and groups of up to 12. Unwind in the fenced backyard with a BBQ, a large year-round swim spa, or a 10-person hot tub! Conveniently located near lakes, parks, shopping, and Omaha’s best attractions, this home offers the perfect mix of comfort and adventure. Get ready for an unforgettable getaway filled wi

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.

Urban Oasis Studio

Escape to our Charming Guesthouse a perfect blend of comfort and relaxation. Step outside to enjoy a peaceful patio with a soothing waterfall. Stay comfortable A/C and heating, and cozy up next to the beautiful fireplace. High-speed Wi-Fi and a large TV are provided for your entertainment. On a fenced 3/4 acre lot, access to an outdoor firepit perfect for evening relaxation. Located in the heart of Omaha, you’ll enjoy full city access while still retreating to a peaceful, private setting.

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.

Private Space, Walk-Out Basement of suburban home.

Our cozy, quiet, home backs to walking trail, creek & prairie. Easy access to interstate, restaurants & shopping. You have private access to our walk-out basement w/bedroom, living room, bathroom, and kitchenette, + board games, books, ping pong, our backyard and a nearby park. The bedroom has a Cal King bed & dark, cool sleeping. The family room includes two twin beds and a twin mattress on floor, plus our large comfy sofa and floor to ceiling windows showcasing our green space.

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. 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.

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.

*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. Large off street parking for 2 cars. Washer & Dryer in basement. Furry family members welcome. Fully fenced back yard.

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.