
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 $14 CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Middletown vacation 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 vacation rentals in Middletown
Guests agree: these stays are highly rated for location, cleanliness, and more.

Home w/ King Bed & Fire pit centrally located
Come stay at our private, simple, fully equipped home centrally located between Cincinnati and Dayton. This home is perfect for a small family looking for a peaceful stay or a busy traveler wanting a private place to unwind. It includes 2 bedrooms (master with a king 2nd bedroom with a twin and trundle bed), living room (sofa bed), 1 bath, and 1 full-size kitchen. There is plenty to do within driving distance including bars and restaurants or relax at home and watch your shows on the Smart TV.

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!

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

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.

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.

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 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.

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!

The Camp in Oxford (OH)
The Camp in Oxford includes3 private acres nestled right alongside the Indian Creek River and surrounded by sprawling farmland. Located just 5 miles from Miami University, 13 miles from Brookville Lake and short drives to Hamilton, Cincinnati or Dayton, this beautiful 2 bedroom modern cottage is waiting for your next visit. Fully furnished and equipped with every amenity you'd expect from a 5 star property.

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.

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 vacation rentals
Stay near Middletown's top sights
Other great vacation rentals in Middletown

“The Carriage House”

Happy Place Haven!

Quiet rustic retreat

NEWLY built sanctuary. Come make yourself at home!

Stanley Cozyside

Tuscan Suite

Private Large Suite, cozy, quiet & close to I-75

FoosBall~SpookyNook~Theatre~GameRm~KingBD~Firepit
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $178 CAD | $183 CAD | $147 CAD | $178 CAD | $205 CAD | $216 CAD | $240 CAD | $250 CAD | $221 CAD | $223 CAD | $197 CAD | $172 CAD |
| 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.
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- Kings Island
- Great American Ball Park
- Creation Museum
- Cincinnati Zoo & Botanical Garden
- Cincinnati Music Hall
- Perfect North Slopes
- Paycor Stadium
- Newport Aquarium
- University of Cincinnati
- University of Dayton
- John Bryan State Park
- Xavier University
- Cincinnati Art Museum
- Hard Rock Casino Cincinnati
- Big Bone Lick State Historic Site
- Smale Riverfront Park
- TQL Stadium
- Jungle Jim's International Market
- Eden Park
- National Underground Railroad Freedom Center
- Newport On The Levee
- Contemporary Arts Center
- Findlay Market
- Krohn Conservatory





