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Holiday rentals in Middletown

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Quick stats about holiday rentals in Middletown

  • Total holiday rentals

    Explore 50 holiday rentals in Middletown

  • Nightly prices starting at

    Middletown holiday rentals start at €18 per night before taxes and fees

  • Verified guest reviews

    Over 1,430 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Middletown holiday rentals include wifi 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 holiday rentals in Middletown

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

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Guest favourite
Apartment in Lebanon
4.94 out of 5 average rating, 17 reviews

Tuscan Suite

Welcome to the perfect stay in the heart of downtown Lebanon. The apartment is nestled within this picturesque historic district, offering a walkable, welcoming atmosphere for all! Looking for activities? Whether you’re here for shopping, sports, or relaxation, everything is conveniently close. One block to the Golden Lamb. Combining small-town charm with unbeatable location, ideal for weekend getaways, business trips, or extended stays. Come experience history, convenience, and comfort.

Top guest favourite
Guest house in Lebanon
4.95 out of 5 average rating, 503 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 favourite
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.
Guest house in Hamilton
4.98 out of 5 average rating, 255 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.

Superhost
Home in Middletown
4.97 out of 5 average rating, 37 reviews

New Pet Friendly Home in Middletown Minutes to I75

Whether it is work or play that brings you to Middletown, Ohio; this brand-new home has everything you need. It's quiet, comfortable, and not too far from the city of Middletown. Centrally located just outside the City of Middletown, our home provides all the amenities you need to be home. It also has a relaxing covered porch. Modern farmhouse design and TV's in every room. We provide everything you need. This home is meticulously decorated and we know you will love it! Come see us!

Top guest favourite
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.
Guest house in Springboro
4.97 out of 5 average rating, 115 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 favourite
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 favourite
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.'
Guest house in Centerville
5 out of 5 average rating, 275 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 favourite
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.
Flat 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 favourite
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!

Top guest favourite
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.
Flat 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.

Guest favourite
The bathroom features a white vanity with a marble countertop and dual sinks. A large framed mirror is mounted above the sink, reflecting natural light. Decorative artwork is displayed on the wall, and a door leads to the main area.
Home in Hamilton
4.96 out of 5 average rating, 134 reviews

Pleasant Dreams - Hamilton, spooky Nook, Miami Unv

Newly renovated spacious home in Hamilton with parking in driveway. Enjoy a peaceful stay at our cozy 2 bedroom 1 bath Home with dedicated work space. Close to Spooky Nook, Miami University and Fairfield. Also easy and close access to Interstae 275 and everything around the loop...Kings Island, Bengals, Reds, Cincinnati Zoo, Creation Museum, Newport Aquarium and much, much more.

Superhost
A spacious sleeping area features a padded headboard with a neatly made bed covered in a dark blanket. Two bedside tables with soft-lit lamps sit on either side, while a framed photograph of rocks hangs above the bed. Natural light enters through a window adorned with gray curtains.
Guest suite in Liberty Township
4.83 out of 5 average rating, 328 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

Popular amenities for Middletown holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Middletown

Home in Germantown
5 out of 5 average rating, 5 reviews

“The Carriage House”

Top guest favourite
The exterior of a single-story home is depicted, featuring light grey siding and a two-car garage. A large flowering tree adds a vibrant touch to the front yard, while a circular bed of mulch enhances the landscaping. The driveway is spacious, providing ample parking.
Home in Franklin
4.94 out of 5 average rating, 17 reviews

Happy Place Haven!

Top guest favourite
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

Superhost
A spacious bedroom features a four-poster bed with a white bedding set. A decorative throw rests at the foot of the bed. A low, brown bench sits nearby, and a wall-mounted shelf displays minimal decor. An area rug complements the dark walls and ceiling.
Hotel room in Middletown
5 out of 5 average rating, 7 reviews

Room 306 - Canopy Gold

Top guest favourite
A calming bedroom features a spacious bed adorned with blue and white pillows, complemented by matching blankets. Two nightstands host lamps and decorative items. The walls are painted in a soft blue, and windows are dressed with dark curtains, allowing natural light to filter in.
Flat in Monroe
4.99 out of 5 average rating, 97 reviews

Renovated 2Bed/1 Bath with King Bed. Pets Welcomed

Home in Hamilton
4.83 out of 5 average rating, 12 reviews

Welcome to your Ultimate home away from home.

A spacious bedroom features a plush bed adorned with decorative pillows. A dining area is visible, highlighted by a round table set beneath a chandelier. The exterior showcases the historic charm of the home, surrounded by well-maintained landscaping.
Home in Middletown
4.56 out of 5 average rating, 126 reviews

Middletown Centenarian 4 Bed 2 Bath Sleeps 12

Top guest favourite
Home in Hamilton
5 out of 5 average rating, 38 reviews

Westside Nook-5 Min Walk2Spooky

When is the best time to visit Middletown?

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Avg. price€112€116€93€115€130€133€152€158€140€141€125€109
Avg. temp-1°C0°C6°C12°C18°C23°C24°C24°C20°C13°C7°C1°C

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.

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