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
Home in Franklin
5 out of 5 average rating, 20 reviews

Franklin 4BR Retreat, Fenced Yard, No Airbnb Fees

Welcome to The Franklin Bison Home– Your Spacious & Stylish Retreat! Experience comfort, convenience, and relaxation at The Franklin Bison Home! This charming 4-bedroom, 2-bathroom home is perfect for families, friends, or groups seeking a memorable getaway. Enjoy a fully equipped kitchen, cozy living spaces, a dedicated workspace, and modern amenities designed for stress-free stays. Step outside to the fenced backyard with comfortable seating — perfect for morning coffee, evening chats, or sim

Top guest favorite
A brown horse stands in a grassy field, surrounded by a white fence. Trees adorned with vibrant autumn leaves create a colorful backdrop, while other horses are seen grazing in the distance. The scene captures the serene atmosphere of the farm.
Farm stay in Lebanon
5 out of 5 average rating, 76 reviews

Farmhouse Stay

Come enjoy a unique home with a view. This is the original farm house on an active working farm. Each bedroom view looks out on horse paddocks. We are located 5 miles from downtown Historic Lebanon, 23 minutes to WEC, less than 35 minutes from downtown Cincinnati, 40 minutes from downtown Dayton and 70 miles to Columbus. The house is on a shared driveway. There are two homes on the farm property. The location is quiet, although you may see people around the property, as we also board horses.

Top guest favorite
Guesthouse in Lebanon
4.95 out of 5 average rating, 502 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 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, 254 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 spacious studio apartment is shown, featuring a king bed with soft linens, a comfortable seating area with a sectional sofa, and a wooden dresser. The kitchenette, equipped with wooden cabinetry and modern appliances, is visible in the background. Soft lighting enhances the welcoming atmosphere.
Guesthouse in Springboro
4.96 out of 5 average rating, 113 reviews

Comfortable Studio In Springboro

Welcome to a quiet, upscale golf course community within walking distance to Old Towne Springboro. Private 438 square foot studio apartment with a king bed, full bath, large kitchen and in unit washer and dryer. This guest suite has its own entrance that is accessed with a keypad. Location: Nestled in the Heatherwoode Golf Course community within walking distance to Old Towne Springboro and 10 min from Austin Landing. 15 minutes from Kings Island and Cincinnati Premium Outlets.

Guest favorite
The exterior of a modern two-story home is presented, featuring a combination of white and dark blue siding. A prominent gabled roof and wooden accents frame the front door. A driveway leads to a two-car garage, and landscaping includes low bushes and a lawn.
Home in Middletown
4.96 out of 5 average rating, 45 reviews

NEWLY built sanctuary. Come make yourself at home!

Enjoy a long or short stay in this beautiful NEW home that includes three bedrooms, 2.5 baths, a two-car garage and a private driveway. Ideal for both families & traveling professionals. This smoke free home has plenty of living and storage space as well as an in-unit laundry suite. The spacious living room has high ceilings, a cozy fireplace, lots of natural light and opens up to a top of the line kitchen. The home also features a private patio and yard for outdoor enjoyment.

Top guest favorite
Home in Hamilton
5 out of 5 average rating, 37 reviews

Westside Nook-5 Min Walk2Spooky

Welcome to the Westside Nook! Nestled on a quiet, charming street, a perfect blend of tranquility & convenience. This stunning home combines peaceful ambiance with a modernized, vintage aesthetic. Just a 5 minute walk from Spooky Nook Sports. You’re also only a short stroll away from the downtown DORA district, where you can explore amazing food, boutique shopping, & local entertainment. Miami University is just a 15 minute drive and about 35 minutes to Cincy & Kings Island.

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, 273 reviews

The Carriage House in the Heart of Uptown

The Carriage House in the Heart of Uptown Centerville!! Historic Charm with Modern Comfort. Built in 1897 and fully renovated in 2017, making it one of Centerville’s true hidden gems. Just steps from 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
A modern kitchen features a large island with three yellow stools, complemented by stainless steel appliances. Natural light enters through a window, illuminating the open space that connects to a cozy living area. A television and decorative elements are visible in the background.
Apartment in Springboro
4.88 out of 5 average rating, 34 reviews

The Odd Fellows Lodge

Our Loft in historic downtown Springboro is beautifully renovated with stylish furniture and decor. The apartment is located in a building that was originally constructed in 1869 as the Odd fellows Lodge. The stylish updates include a state-of-the-art kitchen, a spacious living room with a sofa bed, a comfy king bed in the bedroom, a master bath with many amenities, a gaming room with a Nintendo switch and board games, and a pull-out twin bed.

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, 234 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, 33 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!

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, 163 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. priceﺩ.ﺇ 470ﺩ.ﺇ 485ﺩ.ﺇ 389ﺩ.ﺇ 481ﺩ.ﺇ 544ﺩ.ﺇ 558ﺩ.ﺇ 635ﺩ.ﺇ 661ﺩ.ﺇ 584ﺩ.ﺇ 591ﺩ.ﺇ 521ﺩ.ﺇ 455
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Frequently Asked Questions

  • What are the best places to stay in Middletown?

    Staying near Middletown’s historic downtown connects you with local shops, restaurants, and cultural venues. The riverfront area is frequently suggested for those looking for scenic walks and a relaxed atmosphere.

  • What are the best things to do in Middletown with kids?

    Explore play areas in city parks, or enjoy interactive, family-friendly exhibits at community museums. Local events like fairs and outdoor movie nights are also popular with children.

  • What are some of the best things to do in Middletown?

    Explore the arts at local galleries, discover history museums, or relax in area parks. Middletown has spaces for antique shopping and water activities along the river for those seeking a bit of adventure.

  • How is the weather in Middletown?

    Middletown has cold winters near 22–42°F (−6–5°C), with mild rainfall, and warm summers where afternoons reach 85°F (29°C). Layers and rain gear are handy throughout the year due to changing conditions.

  • When is the best time to visit Middletown?

    Late spring and early fall are often recommended for comfortable temperatures, local festivals, and scenic outdoor spaces. Summer brings river activities, while winter is suited for indoor arts and museum visits.

  • What are the best places to visit in Middletown?

    The Sorg Opera House draws visitors interested in performing arts, and the Canal Museum highlights the city’s transportation heritage. Parks around town provide green spaces for outdoor activities.

  • What are some hiking trails in Middletown?

    Area parks in Middletown have walking and nature trails that wind through forests and along the river. These paths are often recommended for birdwatching and casual outdoor exercise.

  • What are some family activities we can do in Middletown?

    Families often explore local parks with play areas, hands-on exhibits at museums, and nature trails. Middletown also has occasional festivals and art workshops suitable for all ages.

  • What are some of the best day trip ideas from Middletown?

    Discover regional nature reserves, visit nearby small towns for antique shopping, or explore art centers in neighboring communities. Outdoor recreation areas around Middletown are frequently suggested for a scenic escape.

  • Are there any pet friendly accommodations available in Middletown?

    Many vacation rentals in and around Middletown welcome pets, especially near parks and residential areas. Look for listings with open yards or easy access to walking trails for a convenient stay with your animal companion.

  • What are some local tips for visiting Middletown?

    Check out community art walks and seasonal farmers markets for a glimpse into local culture. Dress in comfortable layers, as weather can shift, and ask shop owners about upcoming events or food specialties.

  • What is Middletown known for?

    Middletown is known for its roots in steel manufacturing, a tradition reflected in museums and local history. Its vibrant arts scene, historic theaters, and riverfront are frequently highlighted by residents.

  • What are the best hidden gems to explore in Middletown?

    Middletown has locally owned galleries, vintage shops, and quiet river trails that are less traveled but rich in atmosphere. Creative art spaces and specialty shops showcase the city’s unique character.

  • What are the best foods to try in Middletown?

    Middletown has a tradition of Midwest comfort foods—try local barbecued meats, regional pies, and classic diner-style meals. Locally owned eateries serve homestyle dishes and rotating seasonal specialties.

  • What should I bring for a trip to Middletown?

    Pack comfortable walking shoes for exploring shops and parks, and bring layers—temperatures can range from 22°F (−6°C) in winter to 86°F (30°C) in summer. An umbrella or rain jacket is helpful given periodic rainfall throughout the year.

  • What is the nightlife in Middletown like?

    Nightlife in Middletown is centered around casual bars, local breweries, and venues with occasional live music. Some spots near downtown feature performances and a relaxed, welcoming atmosphere.

  • What are the most popular events or festivals in Middletown?

    Middletown hosts annual arts festivals, heritage celebrations in summer, and seasonal fairs in local parks. Riverfront events and car shows are frequently suggested for visitors looking to experience local traditions.

  • Are there family friendly vacation rentals in Middletown?

    Many vacation rentals in Middletown cater to families, especially those near parks and schools. Look for listings with spacious living areas, kitchens, and child-friendly amenities for a comfortable stay.

Quick stats about vacation rentals in Middletown

  • Total vacation rentals

    Explore 50 vacation rentals in Middletown

  • Nightly prices starting at

    Middletown vacation rentals start at ﺩ.ﺇ 73 per night before taxes and fees

  • Verified guest reviews

    Over 1,430 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 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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