
Holiday rentals in Middletown
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Top-rated holiday rentals in Middletown
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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

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.

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

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.

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.

Happy Place Haven!
Take it easy at this unique getaway retreat, perfect for crafting, quilting, scrapbooking, yoga retreats, company off-sites, or just spending time with friends! This 3-bedroom house sleeps 10 guests, and features a main work area with 10 workstations, each with a lamp and electric. The kitchen is newly remodeled and features everything you need to make delicious meals during your stay. The finished lower level has a large lounge area, perfect for binging your favorite shows!

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

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.

New Inground Pool! Pet Friendly with fenced yard.
Relax in total comfort with your family, and let your group enjoy a nice private backyard oasis with a furnished patio and pool. This property has a crystal clear pool, patio, newly renovated interior, fully equipped laundry, and more. A blend of comfort, modern style, and convenience greets you as soon as you enter our home. While decorating this inviting retreat, we have worked hard to create a home away from home feeling for you and your guests.

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.

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!

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 holiday rentals
Other great holiday rentals in Middletown

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Incredible New Construction home in Middletown, OH

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FoosBall~SpookyNook~Theatre~GameRm~KingBD~Firepit

The Odd Fellows Lodge
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £95 | £98 | £79 | £98 | £110 | £113 | £129 | £134 | £119 | £120 | £106 | £92 |
| Avg. temp | -1°C | 0°C | 6°C | 12°C | 18°C | 23°C | 24°C | 24°C | 20°C | 13°C | 7°C | 1°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.
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 £15 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!
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- Great American Ball Park
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