Holiday rentals in Middletown

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Top-rated holiday rentals in Middletown

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Top guest favourite

Guest house in New Lebanon

4.97 out of 5 average rating, 201 reviews

Cottage on a working market garden

Studio cottage with full bath and self-catering kitchen with pots and pans, etc., queen sized bed with fresh linens and towels provided. This cottage is on a working market garden. Maximum occupancy two adults. We do have a small bed that could be added to accommodate a small child about 6 years and under. WE WILL ACCEPT SOME PETS, BUT NOT ALL. We are one mile from grocery shopping. Local roads ideal for cycling. Thirteen miles west of Dayton. Price includes fresh flowers and vegetables from the garden during the season. One cat on the property. Cottage has ceiling fan and good air circulation and a window air-conditioner during the warmer months. There is a TV that streams Apple TV and Kanopy in the cottage, and excellent WIFI access. National Air Force Museum in Dayton is only 20 miles/ 30 minutes away. University of Dayton is 14 miles/ 20 minutes from the cottage. Dayton International Airport is 21 miles/ 26 minutes away. Your hosts are a hospitable couple who enjoy meeting new people. If no one else is booked after you, we can be more flexible with the check-out time.

Guest favourite

Flat in Centerville

4.89 out of 5 average rating, 284 reviews

Apt 1: Octopus Garden in Uptown Centerville

This apartment is a twin to our Apt 2: Pilot Lounge located across the hall. Two adults can sleep in a dedicated bedroom on a queen bed while your child sleeps on an air mattress (the 2nd bed) in the living room. The kitchen is equipped for basic cooking with a fridge, Keurig, oven, microwave and toaster. 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. Parking is available in the adjacent public lot

Guest favourite

Home in Middletown

4.88 out of 5 average rating, 52 reviews

Hook Field Hideaway

Welcome to Hook Field Hideaway, your ideal short-term rental near Smith Park sports fields (or 23 min to Spooky Nook) and Middletown Regional Airport. Located on a quiet street with plenty of on-street parking for work vehicles, it's perfect for contractors. Enjoy skydiving, airplane spectacles, and hot air balloon adventures nearby. Just a half mile from downtown, you can explore city life or unwind in this peaceful retreat—offering the perfect blend of urban convenience and outdoor thrills.

Guest favourite

Guest house in Maineville

4.96 out of 5 average rating, 219 reviews

The Barn at Serenity Acre

Take it easy at this unique and tranquil getaway, where relaxation abounds. We are located in Warren county, the playground of Ohio. - total and complete renovation in 2021 - fully equipped kitchen - cozy bedroom / living room - spacious bathroom with claw foot tub to soak or shower in, vanity, and robes - walking trails in woods behind our property, access to pool (seasonal), close to restaurants, stores, vineyard, historic towns, very close to Kings Island, bike trails, and so much more

Guest favourite

Flat in Middletown

4.93 out of 5 average rating, 28 reviews

Brewmasters Retreat

This is an efficiency apartment!! Welcome to The Brewmaster's Retreat! Immerse yourself in the history of a former brewery taproom transformed into a cozy getaway. With rustic charm and modern comforts. Explore nearby attractions and breweries, including NEW Ales Brewing, Gravel Road, Steel City Pizza,. The Sorg Opera House, and Central Ave shopping. This is a 2 room efficiency apartment, it has a refrigerator, toaster, coffee pot, electric skillet and crock pot. No oven.

Top guest favourite

Guest house in Lebanon

4.95 out of 5 average rating, 424 reviews

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. 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

Top guest favourite

Guest house in Centerville

5 out of 5 average rating, 194 reviews

The Carriage House in Historic Uptown Centerville

Welcome to the Carriage House. Walk to shops, restaurants, ice cream & more! Whether you're staying for a fun weekend, romantic get away, work or visiting family and friends- the Carriage House is the perfect place. The Carriage House was built in 1897 & underwent a complete renovation in 2017. With its open style concept & 12 ft ceilings, it has taken on a whole new role as one of Centerville's coziest getaways, in the heart of Uptown.

Guest favourite

Home in Hamilton

4.95 out of 5 average rating, 114 reviews

Hamilton Home Away From Home!

Charming Midwestern house, close to Hamilton city-center, Spooky Nook, and Miami University! You and your family will find yourself comfortably at home with everything you need for an enjoyable stay. Take advantage of the freshly updated kitchen, the spacious family room with reclining sofas, and unwind with some fun in the game room. With tree lined streets and a friendly neighborhood you are sure to find yourself at home in Hamilton!

Guest favourite

Home in Middletown

4.9 out of 5 average rating, 178 reviews

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!

Top guest favourite

Flat in Middletown

5 out of 5 average rating, 138 reviews

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.

Top guest favourite

Cottage in Hamilton

4.97 out of 5 average rating, 149 reviews

Four Mile Creek Cottage - Countryside Getaway

Relax and unwind with the whole family at this peaceful countryside getaway. Situated on 4 acres of woodlands greenery, directly overlooking Four Mile Creek, the cottage is tucked away from city noise yet super accessible: 5-minute drive to Spooky Nook Champion Mill and Downtown Hamilton, 15-minute drive to Miami University and Uptown Oxford, 50-minute drive to Cincinnati, 1-hour drive to Dayton, Ohio.

Guest favourite

Guest suite in Liberty Township

4.84 out of 5 average rating, 247 reviews

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

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Other great holiday rentals in Middletown

Guest favourite

Private room in Dayton

4.94 out of 5 average rating, 54 reviews

Cozy Room near Children’s, Downtown, UD

VictorRating, 5 stars1 month ago

Heather, this place is neat and clean and situated in a semi detach with Heather living in the adjacent building. Met her husband sitting on the porch. He was very friendly. A definite plans for me as a cat friendly person is that there are lots of cats in the area. They seem to have adopted the neighborhood. There is one black cat in particular I believe her name is Dora. She loves to come visit and sit on your lap. She is very friendly, but she doesn’t sit for long as she is quite the social butterfly ha ha my daughter was visiting really enjoyed spending time with Dora. The accommodations were lovely with lots of amenities in the kitchen and coffee, of course. Appears to be three rooms. I shared the place with two others. They were very quiet and friendly . I would definitely stay here again. 😄

Guest favourite

Private room in Franklin

5 out of 5 average rating, 7 reviews

Private Jacuzzi Suite for Mature Solo Travelers

DanaRating, 5 stars2 months ago

John's place was everything that it is listed to be. A spacious lower level with a kitchenette, sitting/dining area, two bedrooms with a large and cozy bed, and a nice and clean bathroom. It was easy to get into and there was a friendly pup on the upper level that was a cute to come home to after a hard day at work. Great deal!

Guest favourite

Private room in Liberty Township

4.92 out of 5 average rating, 257 reviews

Quiet neighborhood in a very convenient location

ShaquilleRating, 5 stars2 days ago

the host was absolutely Sweet and kind. she left us snacks and beverages as well as a nice tour of her lovely home. she seems very hard-working which is even cooler for her to take some time out of her work to help us with anything that we needed help with. the neighborhood is beautiful and very quiet. I would highly recommend, especially near the Cincinnati Liberty City area

Home in Middletown

4.83 out of 5 average rating, 6 reviews

Liberty Twp Spacious 4 bedroom house

KarlaRating, 5 stars2 weeks ago

Beautiful home.. description says 3 beds but there are 4 bedrooms and 4 beds!! Great updated home. Host was very quick to respond with any inquiries!

Guest favourite

Private room in Hamilton

4.88 out of 5 average rating, 129 reviews

Secluded Residential Home in the Country.

VictorRating, 5 stars3 weeks ago

This was perfect for my needs while attending my Granddaughters Graduation at Miami of Ohio University, in Oxford. Much better than what I had expected!

Guest favourite

Flat in Springboro

5 out of 5 average rating, 7 reviews

The Odd Fellows Lodge

BrandyRating, 5 stars3 weeks ago

Beautifully and tastefully decorated. It featured modern appliances and fixtures but still maintained the historic feeling of the building. As one other reviewer noted, there are some stairs/steps throughout, but they weren’t a problem. Host provided a selection of coffees and teas as well as all the amenities in the listing. The bed and pillows were super soft and comfortable. The shower was spacious and relaxing. We were only there a few days, but it definitely would be a place that I could see staying comfortably for a week or more.

Guest favourite

Private room in Cincinnati

4.94 out of 5 average rating, 71 reviews

SUITE C Oikos for Digital Nomads- Private Bathroom

MatthewRating, 5 stars1 month ago

Brian was an amazing host, made me feel right at home and my room was perfect. I would definitely recommend staying here as this will be my go to place for when I’m back in town!

Top guest favourite