
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.

Apt 1: Octopus Garden in Uptown Centerville
This apartment is a twin to our Pilot Lounge airbnb located across the hall. Two adults can sleep in a dedicated bedroom on a queen bed while your child sleeps on an air mattress (the 2nd bed) in the living room. The kitchen is equipped for basic cooking with a fridge, Keurig, oven, microwave and toaster. There's a 42" TV paired with an apple TV loaded with multiple apps. Alexa provides info and light control. Two window a/c keep the place cool. Parking is available in the adjacent public lot

The Carriage House in the Heart of Uptown
The Carriage House. Historic Charm with Modern Comfort. Built in 1897 and fully renovated in 2017, the Carriage House blends timeless character, with modern style & comfort, making it one of Centerville’s true hidden gems. Just steps from Uptown 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.

Studio Neutral Chic near Kettering Hospital, Shopp
Come enjoy this quaint unit in Kettering...close to shopping, restaurants, hospitals and city attractions! King size bed, washer/dryer, balcony and tranquil essential oil diffuser will help set the mood and relax you during your stay! Walk or drive to various local and chain restaurants. 9 min drive to Kettering Hospital (main campus)...5 minute drive to The Fraze Pavillion, The Greene Towne Centre. Visit Downtown Dayton/ Oregon District within 15 minutes. Hike Clifton Gorge in Yellow Springs

The Barn at Serenity Acre
Take it easy at this unique and tranquil getaway, where relaxation abounds. We are located in Warren county, the playground of Ohio. - total and complete renovation in 2021 - fully equipped kitchen - cozy bedroom / living room - spacious bathroom with claw foot tub to soak or shower in, vanity, and robes - walking trails in woods behind our property, access to pool (seasonal), close to restaurants, stores, vineyard, historic towns, very close to Kings Island, bike trails, and so much more

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

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.

Hamilton Home Away From Home!
Charming Midwestern house, close to Hamilton city-center, Spooky Nook, and Miami University! You and your family will find yourself comfortably at home with everything you need for an enjoyable stay. Take advantage of the freshly updated kitchen, the spacious family room with reclining sofas, and unwind with some fun in the game room. With tree lined streets and a friendly neighborhood you are sure to find yourself at home in Hamilton!

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.

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

The Cozy Corinth
Welcome to The Cozy Corinth! A peaceful escape from the hustle and bustle of everyday life. Conveniently located just a short drive from downtown Dayton. Note: Please, no parties or events! We are located in a small, quiet neighborhood and cannot accommodate parties or events. Thanks for your understanding.
Popular amenities for Middletown vacation rentals
Other great vacation rentals in Middletown

Spacious Large House By Downtown

Comfy Local Artist’s Guest Suite

Home w/ King Bed & Fire pit centrally located

Cozy Comfort 24

NEWLY built sanctuary. Come make yourself at home!

Cozy cottage in North Middletown

Funky Firehouse Renovated into Modern 2 BDR/1 Bath

Comfortable Studio In Springboro
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $100 | $95 | $104 | $131 | $148 | $152 | $131 | $117 | $113 | $119 | $119 | $112 |
| Avg. temp | 29°F | 33°F | 42°F | 54°F | 64°F | 73°F | 76°F | 74°F | 68°F | 56°F | 44°F | 34°F |
Frequently Asked Questions
Are there family-friendly vacation rentals in Middletown?
Middletown has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Middletown have free parking?
Absolutely! We offer over 30 house rentals with free parking in Middletown. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Middletown have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Middletown. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Middletown?
Experience the best of Middletown with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Where should I stay in Middletown?
Make yourself at home in Middletown by choosing from our most frequently booked neighborhoods. We have over 50 vacation rentals in Mayfield, over 10 vacation rentals in Avalon, and over 50 vacation rentals in Oakland.
Are there vacation rentals with a dedicated workspace in Middletown?
Yes! Work meets play with ease at over 40 vacation rentals in Middletown featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Middletown?
Four-legged friends are welcome in Middletown. Choose from more than 10 vacation rentals for guests traveling with pets.
Do apartment rentals in Middletown have wifi?
Absolutely! We offer over 20 apartment rentals with wifi in Middletown. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Middletown have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Middletown. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Middletown?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 homes with a kitchen, over 30 homes with free parking, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Middletown

Total vacation rentals
Explore 60 vacation rentals in Middletown

Nightly prices starting at
Middletown vacation rentals start at $20 per night before taxes and fees

Verified guest reviews
Over 1,470 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
60 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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