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
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, 256 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.

Guest favorite
The living area features a comfortable couch with patterned upholstery and a juxtaposed love seat. A modern coffee table adds functionality, while barstool seating at the kitchen counter enhances social space. Soft lighting from pendant fixtures and natural light through the window contribute to the room's ambiance.
Apartment in Hamilton
4.93 out of 5 average rating, 101 reviews

Heart of Hamilton#5-Hamilton, Spooky Nook, Miami U

Newly renovated apartment in downtown Hamilton. This place is located in the heart of hamilton. Enjoy a peaceful stay at our cozy 2 bedroom 2 bath apartment with dedicated work space and FREE parking. 2 miles from Spooky Nook. Easy access to Miami University, Fairfield and Interstae 275 and everything around the loop...Kings Island, Bengals, Reds, Cincinnati Zoo, Creation Museum and more. Your family will be close to everything at this centrally-located place. Has 38 steps to enter unit.

Top guest favorite
Guesthouse in Lebanon
4.95 out of 5 average rating, 471 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

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
4.98 out of 5 average rating, 246 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
Tiny home in New Richmond
4.97 out of 5 average rating, 464 reviews

Stargazers' Retreat: A Tiny Home on the Riverside

Welcome to The Stargazers' Retreat at Visions on the River - A Tiny Home community on the Riverside. This newly built tiny home is #1 of 3 and set along the banks of the Ohio River, minutes away from the historic river town of New Richmond, OH and a 25-min drive to Downtown Cincy and Northern KY. This space is perfect for anyone looking to retreat and reconnect with nature. Take part in our adventure! With over 450 Five-Star happy guest reviews we are confident you will love it here!

Guest favorite
A cozy living area features a plush sofa facing a flat-screen TV mounted above a decorative fireplace. A wooden coffee table sits upon a patterned area rug, while a recliner is positioned nearby. Natural light enters through the window, illuminating the neutral-toned walls.
Home in Hamilton
4.97 out of 5 average rating, 114 reviews

3 blocks from Spookynook & on the historical reg.

Steps away from Main Street, this property is close to everything making it easy to plan your visit. It's located on one of Hamilton’s most beautiful streets in the Rossville Historic District, is one of the oldest rental properties in the county, and is the on the historic registry. However, the unit is completely remodeled and updated with stainless steel appliances, subway tiled kitchen, ceramic tile shower surround, and laminate vinyl plank throughout. A cool, quaint place!

Superhost
A spacious living area is highlighted by high, open beam ceilings and exposed brick walls. Natural light fills the room through large windows adorned with soft drapes. A chandelier hangs above, while a comfortable sofa and a round coffee table create a welcoming gathering space.
Loft in Richmond
4.85 out of 5 average rating, 468 reviews

THE STARR LOFT Earlham, IUE, Reid, Relaxing Swing!

Second floor of an 1865 Tin shop, industrial building. High, open beam ceilings & exposed brick walls. Bathroom features a soaker tub plus a lux walk in shower. The kitchen features quartz counters, a large farmhouse sink, really nice appliances and thoughtful touches everywhere. The wifi is excellent. Have issues with stairs? This is not a good choice for you. If you're up for stairs and want a unique slice of history in a hip package then you will not be disappointed.

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, 212 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 favorite
A rustic two-story home is nestled among lush greenery, featuring a wooden deck with an umbrella. A stone pathway winds through natural landscaping, leading to the entrance, while trees frame the peaceful setting, enhancing the connection with nature.
Apartment in Tipp City
4.87 out of 5 average rating, 248 reviews

Heartland - Ground Level, 1st Floor

Take it easy at this unique and tranquil getaway. We invite you to exlore this hidden gem just outside of Tipp City, OH. Guests will enjoy a private bedroom, bathroom, kitchen, living area, and designated patio space all to themselves. Guests will enjoy the tranquil atmosphere and beautiful natural landscape with nearby biking or hiking trails. Grill out, make a fire, enjoy peaceful walk on the labyrinth and so much more.

Top guest favorite
A spacious living room features warm hardwood flooring and ample recessed lighting. A large sectional sofa sits on a decorative rug, facing a flat-screen TV. Windows allow natural light to illuminate the space, with a bar area and a few stools in the background.
Apartment in Oregonia
4.98 out of 5 average rating, 130 reviews

Green Acres Farm-Apartment

Reconnect with nature at this unforgettable escape on a farm in the heart of Warren County. Private 900 sq. ft. two bedroom, 1 bath, living room and kitchenette looking out over 18 acres of privacy. Minutes to Caesar’s Creek Lake and hiking trails, the Renaissance Festival, Little Miami River canoeing and bike trails, Kings Island and World Equestrian Center. Right in between Cincinnati and Columbus minutes off of I-71.

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, 155 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 favorite
The living room showcases a cozy seating arrangement with a patterned couch and armchair. A wooden coffee table is placed on a textured rug, and a wall-mounted television is visible. Natural light enters through a large window, framed by orange curtains.
Cottage in Hamilton
4.98 out of 5 average rating, 173 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.

Popular amenities for Middletown vacation rentals

When is the best time to visit Middletown?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ367ﺩ.ﺇ349ﺩ.ﺇ382ﺩ.ﺇ481ﺩ.ﺇ544ﺩ.ﺇ558ﺩ.ﺇ635ﺩ.ﺇ661ﺩ.ﺇ584ﺩ.ﺇ591ﺩ.ﺇ521ﺩ.ﺇ455
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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.

  • 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.

  • Are there pet-friendly vacation rentals in Middletown?

    Four-legged friends are welcome in Middletown. Choose from more than 20 vacation rentals for guests traveling with pets.

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

    Yes! Work meets play with ease at over 30 vacation rentals in Middletown featuring dedicated workspaces. Stay connected and productive 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.

  • Do apartment rentals in Middletown have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning 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.

  • Do apartment rentals in Middletown have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Middletown have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in Middletown. Enjoy a tailored experience with all the comforts you desire.

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

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with free parking, 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 ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 1,560 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 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!

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