Holiday rentals in Middletown

Apt 1: Octopus Garden in Uptown Centerville

This apartment is a twin to our 'Pilot Lounge' airbnb located across the hall. Two adults can sleep in a dedicated bedroom on a queen bed while your third guest sleeps on a twin roll-away bed. The kitchen is equipped for basic cooking with a fridge, Keurig, oven, microwave and toaster plus tableware. There's a 42" TV paired with an apple TV loaded with multiple apps. Alexa provides info and light control. Two window a/c keep the place cool. Free parking is available in the adjacent public lot.

The Carriage House in the Heart of Uptown

The Carriage House. Historic Charm with Modern Comfort. Built in 1897 and fully renovated in 2017, the Carriage House blends timeless character, with modern style & comfort, making it one of Centerville’s true hidden gems. Just steps from Uptown local restaurants, coffee shops and a scoop (or two) of Graeter’s Ice Cream. It’s perfectly located for your stay. Whether you’re planning a romantic weekend, visiting family, or simply looking to relax, this cozy retreat is the ideal place to unwind.

Private carriage house on 3 acres!

New for 2024/2025... updated furniture with memory foam sleeper sofa, memory foam king and queen beds, additional twin mattress for floor for extra sleeping options. Outdoor conversation area! Bright and airy carriage house, located behind main house on 3 acres in Lebanon, Ohio. Close to downtown Lebanon, Springboro, Waynesville and short drive to Kings Island. -Kings Island 11 miles -Warren County Sports Park 7 miles -Roberts Center Wilmington 20 miles -Caesar Creek State Park 10 miles

Newly Remodeled Two Bedroom rental unit

Newly Remodeled, Pet Friendly, King & Queen Beds, Washer&Dryer in unit, Smart TV's in every room, Alexa, Keyless Entry. For children: high chairs, Pack and Play's with thick mattresses, Air Mattress. 2 miles from I-75, Close to Kings Island, Miami Valley Gaming Casino, Flea Markets, Premium Outlet Mall, Centrally located between Dayton and Cincinnati, 30 minutes to Cincinnati Reds, Bengals, Dayton Dragons. Close to Lebanon Sports Complex & Warren County Sports Park

The Linden Guesthouse - bike/hike/golf/shop/visit

This updated stylish 2 bed/1.5 bath single story guesthouse is perfect for work, group trips, fun, or family visits. The kitchen has dishes, cookware utensils, and pantry basics (oil, seasonings, sugar & flour). A Keurig single-serving and carafe coffee maker with k-cups and coffee filters is provided. The guesthouse has two living spaces, a dining room, a kitchen, a utility room with a washer and dryer, a private patio with outdoor seating, and a grill.

Northside Hideaway

The 'Northside Hideaway' is a cozy, quiet studio connected to my newly renovated home nestled in the hills of Mt. Airy Forest in Northside. Just minutes from Clifton, Over The Rhine, and Downtown Cincinnati, It provides the perfect amount of urban serenity. PLEASE NOTE: There is a STRICT TWO GUEST MAXIMUM for all reservations. No exceptions. *Also, there is a 24 HOUR SECURITY camera on the front porch for guests & the space alike.*

New home & huge yard! 3-bd, 2 baths with game room

Enjoy our spacious master bedroom, brand new furniture, peaceful backyard with a 2 person hot tub, BBQ grill, fully equipped kitchen, game room, convenient parking, and 3 spacious bedrooms. We have everything you need to stretch your legs and relax. Ideal for visiting sights in Cincinnati (25 min) or Dayton (15 min) as well as King's Island (15 min). Close to shops, restaurants, and entertainment. Kids and families are welcome!

5 Minute Call

"5 Minute Call" is located next to the Middletown Regional Airport (home of ​Start Skydiving) and Smith Park. ​ The house is a 1 minute walk to the airport, 2 minute walk to Smith Park, 23 min drive to Spooky Nook, 29 min drive to Miami University Oxford. With an arcade set-up in the basement, large kitchen dining table, and theatre-like living room, the house has multiple rooms for gathering with friends and family.

SouthView Acres (No Hidden Fees!)

We are ready to welcome you to SouthView Acres! Enjoy a comfortable stay in our mother-in-law suite with its own private entrance. Private parking, quiet location and minutes away from I75 access. Enjoy cable TV and wifi. Our home is on 10 acres where you are welcome to walk the trails or warm yourself by the fire pit at night. A convenient location for business or pleasure travelers. No hidden fees.

Adorable studio with brand new furniture

Enjoy a stylish experience at this centrally-located place. In a quiet peaceful and safe neighborhood. Close to the Liberty mall, Children’s Hospital, Kings Island, great restaurants and bars. Private entrance, full out sofa to create extra sleeping space, full bathroom, it is an absolutely smoke free environment so there will be a $250.00 fee if you smoke inside the unit

Short walk to Spooky Nook & Main St./downtown area

Centrally located to the Hamilton area, we are only 2 short blocks away from the Spooky Nook Sports facility. Only a short drive(20 mins)to Miami University in Oxford for a visit with your student, and only mile to Main Street restaurant and entertainment DORA district. Come enjoy the many events and amenities now available in Hamilton on your visit.

Charming 1 Bedroom Rental on Historic Dayton Lane

Take yourself back in time in this totally renovated 1884 Victorian Home. Original Parquet Wooden floors and Built in's showcase this beautiful space in this historic home. On the grounds is also a Carriage House that used to make carriages back in the day. Oh the stories these walls could tell!!!