Vacation rentals in Middletown

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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 37 per night before taxes and fees

  • Verified guest reviews

    Over 1,450 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!

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
4.96 out of 5 average rating, 28 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

Guest favorite
The spacious living area features a stone fireplace and a modern ceiling fan. A large sectional sofa is positioned for comfort, facing a wall-mounted TV. Natural light floods the space, highlighting the open layout that connects to the dining and kitchen areas in the background.
Home in Mason
4.94 out of 5 average rating, 111 reviews

Cheerful 4 bedroom home w/ fireplace & game room

Centrally-located w/ high-end finishes. Walk or ride bikes to shops & restaurants in downtown Mason & make memories in the large, fenced backyard with firepit, and gas grill. Game room complete w/ ping-pong, air hockey, pop-a-shot basketball & more! Two bedrooms w/ queen beds; bedroom three w/ two bunk beds & trundle; loft w/ sofa bed. Gourmet kitchen w/ large island; fireplace in family room; Finished lower level w/ theater area & infrared sauna. Off-street parking for up to 10 cars!

Top guest favorite
Guesthouse in Lebanon
4.95 out of 5 average rating, 512 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
A two-story home features a welcoming front porch with seating and large windows. Lush green grass surrounds the foundation, with fresh landscaping and trees providing shade. The house has a neutral exterior, accented by dark shutters, and a paved pathway leading to the entrance.
Home in Hamilton
4.96 out of 5 average rating, 99 reviews

Close to entertainment, shopping and restaurants

Come and stay at our beautiful and fully remodeled home in Hamilton. It's just up the hill from Spooky Nook and from the Main Street entertainment district and next to the hospital. It is fully equipped with just about anything you need during your stay including an outdoor dining area with a bbq grill and a private backyard patio. With 2.5 bathrooms available and 3 different tv's, there will be very little waiting for anything. Includes a Queen size, full size, and two twins (bunks).

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, 260 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, use our stand-up paddleboards, 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
4.97 out of 5 average rating, 120 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
Guesthouse in Middletown
5 out of 5 average rating, 15 reviews

Shamrock Farm Guesthouse

Welcome to Shamrock Farm. This charming one-bedroom, one-bath retreat sits just behind the main house, offering complete privacy and a warm, inviting atmosphere. Step inside to find a cozy, thoughtfully furnished space perfect for solo travelers or couples looking to unwind. Outside, a spacious private deck overlooks four serene acres of open land, giving you plenty of room to relax, sip your morning coffee, or enjoy a quiet sunset while your furry friend enjoys the fenced yard.

Top guest favorite
Cottage in Lewisburg
4.99 out of 5 average rating, 220 reviews

The Cottage Retreat

Whether you are looking for a place to spend some time or just passing through we think you’ll find it quite lovely here. We are just 5 mile off of I70 and centrally located among many places of interest. Go out or stay in. The outdoor living space is pretty spectacular! Private, with a hot tub, fire pit (wood provided), turf to play corn hole. Inside delivers all the comforts of home with full kitchen, laundry, workspace and cozy fireplace.

Superhost
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
4.89 out of 5 average rating, 240 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
4.92 out of 5 average rating, 36 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, 166 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, 184 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?

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Avg. priceﺩ.ﺇ 470ﺩ.ﺇ 485ﺩ.ﺇ 389ﺩ.ﺇ 470ﺩ.ﺇ 544ﺩ.ﺇ 573ﺩ.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.