Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
The spacious bedroom features a large adjustable split king bed with a premium mattress and crisp white bedding. Nightstands with lamps are positioned on either side of the bed, while a recliner is placed nearby. Natural light enters through the window, illuminating the neutral wall tones and carpet.
Guest suite in Liberty Township
4.98 out of 5 average rating, 115 reviews

Suite Liberty – Clean/Spacious

Our lower level, walk out suite (private entrance) has all you are looking for & more. The 1000 sf plus suite is spacious & comfortable. We are located on 2 peaceful acres in a residential area near the Liberty Way Exit off I-75. NOTE: If booking for December through February 28th. We will NOT have snow removal services. Snow melt & shovel will be available to our guests. Please check the weather before your arrival. The reservation can be cancelled 1 day prior to arrival with full refund

Guest favorite
A simple, autumn red cottage is framed by a well-maintained yard, featuring a white picket fence. A welcoming front porch with steps invites entry. Mature trees are visible in the background, and a long driveway extends beside the house.
Home in Middletown
4.82 out of 5 average rating, 17 reviews

Home w/ King Bed & Fire pit centrally located

Come stay at our private, simple, fully equipped home centrally located between Cincinnati and Dayton. This home is perfect for a small family looking for a peaceful stay or a busy traveler wanting a private place to unwind. It includes 2 bedrooms (master with a king 2nd bedroom with a twin and trundle bed), living room (sofa bed), 1 bath, and 1 full-size kitchen. There is plenty to do within driving distance including bars and restaurants or relax at home and watch your shows on the Smart TV.

Top guest favorite
An inviting living area features a large brown leather sofa, a patterned area rug, and a decorative coffee table atop wide plank wood floors. A cozy corner chair and a lamp add warmth, while the back wall showcases a mural with 'Centerville Carriage.'
Guesthouse in Centerville
5 out of 5 average rating, 242 reviews

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.

Top guest favorite
Guesthouse in Lebanon
4.95 out of 5 average rating, 458 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. 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

Guest favorite
The climbing gym features a wooden structure with high ceilings and sloped roofs. Colorful holds are mounted on the walls, complemented by various climbing accessories like mats and silks hanging from the beams. An inviting atmosphere promotes active engagement and community interaction.
Guest suite in Cincinnati
4.97 out of 5 average rating, 148 reviews

The CRUX Climbing Getaway

Welcome to The CRUX Sanctuary Community Climbing Gym! This retro inspired space is a perfect getaway for experienced climbers, small families, or anyone looking for a fun place to stay in Cincinnati. Conveniently located just 5 minutes from downtown Cincinnati, and a short drive from amazing views, diverse restaurants, and local attractions. This remodeled and 100% solar powered church is one of many unique spots in our Price Hill neighborhood. Find us by searching for thecruxsanctuary.

Top guest favorite
The living area features wooden walls and a stone fireplace, complemented by soft-glow electronic candles. A cozy armchair is positioned near a window, while a round, textured coffee table sits at the center, adorned with a vase of dried flowers.
Guesthouse in Hamilton
4.99 out of 5 average rating, 237 reviews

Waterfront Cabin | Peaceful Pondside Escape

Seeking an escape for some peace and quiet? Welcome to The Little Cabin retreat, located on our 50-acre family farm in Ross, Ohio! Let us take you away from the distractions of life to a place where you can soak up nature in a cozy cabin, all within 30 minutes of downtown Cincinnati. You may fish in the lake if you'd like, or take a ride in the paddle boat, or simply enjoy sitting on the porch listening to the birds. Chances are, you may spot wild turkey or whitetail deer scampering by.

Top guest favorite
A dining area features a wooden table set for four, complete with plates and glassware. Soft lighting is provided by a chandelier above. Dark leather chairs surround the table, and a sign with the word 'blessed' is mounted on the wall, complementing the modern kitchen visible in the background.
Apartment in Monroe
4.98 out of 5 average rating, 146 reviews

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

Top guest favorite
A cozy living area showcases two cream-colored couches positioned around a dark coffee table. Natural light enters through a large window, enhancing the space. A sleek ceiling fan is visible, and a small dining area is arranged with a table and two chairs against the wall.
Home in Miamisburg
4.95 out of 5 average rating, 193 reviews

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.

Guest favorite
A single-story house is depicted, featuring light-colored siding and a sloped roof. A two-car garage is present, with a neatly paved driveway leading to the entrance. Lush green grass surrounds the home, complemented by a leafless tree in the front yard.
Home in Middletown
4.9 out of 5 average rating, 203 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!

Guest favorite
A spacious living room features two leather sofas positioned around a coffee table, with a large flat-screen TV mounted on the wall. Natural light illuminates the area, complemented by a stylish rug and decorative accents on a console table.
Home in Middletown
4.91 out of 5 average rating, 22 reviews

Cute Ranch home Middletown, OH

Whether it is work or play that brings you to Middletown, Ohio; our home has everything you need. It's quiet, comfortable, and not too far from the city of Middletown, Miamisburg, and Hamilton. It has a large yard and a relaxing covered porch. There's a 75 Inch flat screen in the main room and each bedroom has its own 65-inch flatscreen smart TV. This home is meticulously maintained and we know you will love it! Come see us!

Guest favorite
A living room is depicted with a television mounted on a wooden stand, flanked by two comfortable reclining chairs and a sectional sofa. An aviation-themed artwork hangs above, while a sleek, metal coffee table adds a modern touch. Natural light enters through windows with light blinds.
Home in Middletown
4.92 out of 5 average rating, 112 reviews

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.

Top guest favorite
The exterior of a single-story brick home is shown, featuring a double garage, manicured lawn, and flower beds with yellow blooming flowers. A driveway leads up to the home, surrounded by peaceful greenery and trees in the background.
Apartment in Middletown
5 out of 5 average rating, 151 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.

Popular amenities for Middletown vacation rentals

When is the best time to visit Middletown?

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Avg. price$100$95$104$131$148$152$173$180$159$115$119$112
Avg. temp29°F33°F42°F54°F64°F73°F76°F74°F68°F56°F44°F34°F

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Middletown?

    Middletown has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Middletown have free parking?

    Absolutely! We offer over 30 house rentals with free parking in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Middletown have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in apartment rentals in Middletown?

    Experience the best of Middletown with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Where should I stay in Middletown?

    Make yourself at home in Middletown by choosing from our most frequently booked neighborhoods. We have over 10 vacation rentals in Avalon, over 50 vacation rentals in Oakland, and over 50 vacation rentals in Mayfield.

  • Are there vacation rentals with a dedicated workspace in Middletown?

    Yes! Work meets play with ease at over 20 vacation rentals in Middletown featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Middletown?

    Four-legged friends are welcome in Middletown. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Middletown have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Middletown have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Middletown?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 homes with free parking, over 30 homes with wifi, over 30 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Middletown

  • Total vacation rentals

    Explore 60 vacation rentals in Middletown

  • Nightly prices starting at

    Middletown vacation rentals start at $20 per night before taxes and fees

  • Verified guest reviews

    Over 1,470 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Middletown vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Middletown rentals

  • 4.8 Average rating

    Middletown stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

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