Holiday houses in Chicago

Dottie the 1969 Vintage Camper for Glamping

Enjoy our kitschy 1969 camper tucked away in the woods of a private neighborhood in the city, it's a vintage glamping dream! Cozy and comfortable with a cushy bed (A few inches shy of a double. 6ft 3in x 4ft), it's a playhouse for grownups! The camper sits in its own corner of our property, surrounded by 1 acre of beautiful gardens. Tucked near a creek and trees with a fire pit and hammock, it's a perfect couple's get-a-way close to coffee shops, dining and shopping. Ceiling hight is 70" inside.

Location · Checkout · Decor

Charming riverfront house

This quiet & serene riverfront house is the perfect setting for a family, nature lovers, fishermen, anniversaries, friends retreats, or honeymooners! Newly remodeled in 2018, we can sleep up to 12. Located just a couple of miles outside of Elkhorn & directly on the Elkhorn River, this is a nature-lovers haven! Local restaurants, shopping & other amenities in Elkhorn, Omaha & Waterloo are within a few minutes drive! Our place is a smoke & pet free home! Smoking is allowed in outdoor areas only.

Location · Family · River

Private Suite with Nature Views-Full Washer/Dryer

Backing to a wooded creek this home away from home is sure to be the relaxing place you are waiting for. This is a separate entrance lower level walkout apartment complete with kitchen, laundry, spacious bedroom, and 3/4 bath. Amenities include fiber gigabit high speed internet, smart TV (w/ Netflix), coffee bar able to brew ground coffee or K Cups, and dedicated off street driveway parking for two vehicles parked tandem. Please reach out if you have special requests or accommodations in mind?

Value · Family · Indoor spaces

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.

Location · Family · Decor

Family Fun Basement Retreat w/ Hot Tub Near Dining

Spacious Basement Retreat – Private Entrance This rental is for the basement level only, with a private entrance and a locked door separating it from the upstairs. 2 private bedrooms, a daybed with trundle, 1 full bath, living room with TV, and bar area that seats 4. Fun extras: foosball table, shuffleboard, hot tub, outdoor TV, and board games. The backyard backs up to trees, offering a peaceful and quiet escape. Just minutes from local attractions, dining, shopping, and family fun!

Family · Value · Cleanliness

“The Duke” in Charming Old Towne Elkhorn

The Duke, is a roomy, stylish downtown Elkhorn retreat. Comfortably sleeps up to 8 with a king suite, a queen bedroom, & a third room with two full beds. 6 person Hot Tub Cook & bake to your heart’s content in a fully stocked kitchen (grill-ready tools included). Step outside onto the deck, enjoy fully fenced yard w/ morning coffee or evening drinks, & enjoy access to the shared hot tub for a relaxing soak after a day exploring Elkhorn. Perfect for families, groups, or weekend getaways.

Location · Family · Quiet

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.

Location · Family · View

Stylish W. Omaha House. Shopping. King Suite.

This spacious 3 bedroom, 2.5 bath house rental is the ideal space for groups and families. Tucked away in a peaceful residential neighborhood, you can enjoy a tranquil and private stay while still having quick and easy access to the city's main road, W. Dodge (US Hwy 6). Plus, with the popular Village Pointe shopping mall just a short 5-minute drive away, you can indulge in some retail therapy or treat yourself to a delicious meal at one of the many restaurants in the area.

Value · Location · Cleanliness

Exquisite Elkhorn Experience

Come experience Elkhorn at its finest! Brand-new 5-bed, 3-bath ranch in the desirable South Elkhorn/Gretna area! This spacious home features an open-concept living, dining, and kitchen area, a finished basement, and a fenced backyard. Modern finishes and plenty of room to spread out make it the perfect home base for families, business travelers, medical stays, sports teams, and extended visits. Conveniently located near shopping, dining, parks, and easy access to Omaha.

Access · Comfort · Indoor spaces

Executive Rental 5BR+5BA | Arcade, GYM, Grill

Discover this completely renovated, fully furnished executive rental in West Omaha. This stunning 2-story home features gorgeous curb appeal and a light, airy feel. With 5 beds, 5 baths, a 3-car garage, and over 4300 sqft, it offers ample space for the whole family. Every bedroom has access to its bathroom. The home is fully furnished with all modern new furniture. The open foyer with soaring ceilings and a grand staircase leave a lasting impression.

Location · Value · Cleanliness

Cheerful 3 bd home with easy access to interstate!

A fun home great for a family or multiple adults! 3 bed, 2.5 bath home, that sleeps 8. Located in a quiet, friendly family neighborhood in West Omaha. Located close to top notch outdoor shopping and fantastic restaurants (Village Pointe). Around the corner from the MARK family fun center and UBT sports center! 25 min drive to downtown Omaha. Amenities: Free Wi-Fi, 2 TV's, Patio, Grill, Spacious Back Yard, 2 car garage, Full Kitchen, Laundry.

Location · Family · Comfort

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.

Value · Family · TV