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.

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Guest favourite

Apartment in Franklin

4.9 out of 5 average rating, 143 reviews

Cozy Studio-Eat in Kitchen-5 min off I-75 Franklin

Enjoy a relaxing stay at this newly renovated studio apartment (sleeps up to 2) - Queen bed, full bath with tub, equipped kitchen with appliances, smart TV with high speed internet, and washer/dryer. This apartment is on a main street and within a 3 unit building (with separate entrances). It is located 2.1 miles off I75 (approx. 5 min) and close to The Little Miami Scenic Bike Path! Check in/out with key pad. Parking is close to apartment entrance in the driveway and behind the building.

Jul. 31 – Aug. 7

$135 CAD per night

Guest favourite

Guesthouse in Loveland

4.98 out of 5 average rating, 483 reviews

Retreat to a Boho Chic Guesthouse in a Leafy Family Suburb

Get comfy swaying in the macrame hammock in a living room with a Moroccan vibe. Make breakfast in the bright kitchen and snuggle up on a cozy banquette. This guest house shares a driveway with our home, but it is completely detached and private. The bedroom sleeps two on a queen mattress, and we provide a queen sized inflatable mattress that fits easily in the living room. The property has a stocked kitchen, a washer and dryer, a lovely new bathroom, a two-car garage, and loads of aesthetic.

Nov. 29 – Dec. 6

$206 CAD per night

Guest favourite

Guesthouse in Maineville

4.97 out of 5 average rating, 153 reviews

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

Apr. 8 – 15

$208 CAD per night

Guest favourite

Place to stay in Waynesville

4.97 out of 5 average rating, 195 reviews

Cozy private suite/Ohio to Erie/Miami Scenic Trail

Location is everything in this cozy accommodation catering to weekend guest and bicyclers on the Miami Erie Trail. Enjoy the quaintness of small town living in your one bedroom private cottage suite. You will have everything you need in this historic haven, made contemporary, for a relaxing stay. Walk to cafes, vintage shops, & drive a few minutes to Caesars Creek State Park & Rivers Edge Livery. Opt for breakfast on the go for an additional fee w/ homemade granola, protein and fresh fruits.

Jul. 26 – Aug. 2

$142 CAD per night

Guest favourite

Cottage in Morrow

4.96 out of 5 average rating, 124 reviews

Rossburg Tavern (1800’s)

This house was built in the early 1800's as part of a small town "Rossburg" that no longer exists and is reported to have been a Tavern. This is one of the last remaining structures for this town along with the barn and house across the street. The house sits on one acre of land surrounded by farmland, so you'll have opportunity to relax by a campfire, enjoy the unique architecture of the house, or explore the wide variety of entertainment options all within 20 minutes of the house.

Nov. 12 – 19

$157 CAD per night

Guest favourite

Home in Middletown

4.88 out of 5 average rating, 113 reviews

Huge yard! 3-bedroom, 2 bath home right off I-75.

Enjoy our spacious master bedroom, brand new furniture, peaceful backyard with a 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! We care about our home and the guests that come to use it.

Jul. 6 – 13

$255 CAD per night

Guest favourite

Guesthouse in Fairborn

4.98 out of 5 average rating, 283 reviews

Cozy cabin at The Armstrong Homestead

The caretaker's cabin is a quaint one bedroom suite complete with a full bath, microwave, mini fridge and coffee. Off road parking and a secluded entry makes the cabin perfect for a romantic or working getaway. Located next to the Osborn Historic District in the heart of Fairborn, the Armstrong Homestead is an easy stroll to the downtown shops and restaurants. Xenia Dr provides direct access to the main highways, making most of Dayton reachable in 30 min or less.

Jan. 19 – 26

$106 CAD per night

Guest favourite

Apartment in Centerville

4.89 out of 5 average rating, 214 reviews

Cozy apartment in Centerville's Uptown District

This remodeled apartment is the twin to our popular Airbnb apartment located across the hallway. Two adults can sleep in a dedicated bedroom on a queen size bed and your child can sleep on an air mattress (the 2nd bed) in the living room. The kitchen is well-equipped with a stove, refrigerator, microwave, Keurig Coffee machine, toaster, & cooking basics. There's a smart TV, apple TV, and Alexa in the Living Room.

Nov. 3 – 10

$111 CAD per night

Guest favourite

Apartment in Middletown

5.0 out of 5 average rating, 105 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.

Dec. 8 – 15

$149 CAD per night

Guest favourite

Cottage in Hamilton

4.97 out of 5 average rating, 106 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.

Apr. 19 – 26

$256 CAD per night

Guest favourite

Home in West Alexandria

4.9 out of 5 average rating, 238 reviews

Historic Midcentury Lustron Home

Restored 1000 square foot Lustron home in southwestern Ohio near Dayton, Oxford and I-70, now available again after two years off Airbnb. It offers architectural and historical features, 1950s furniture and accessories, and modern amenities. Located in a small village near cities, with access to both urban activities and small town charms.

Feb. 11 – 18

$134 CAD per night

Guest favourite

Apartment in Hamilton

4.92 out of 5 average rating, 168 reviews

Charming 1 Bedroom Rental on Historic Dayton Lane

Take yourself back in time in this totally renovated 1884 Victorian Home. Original Parquet Wooden floors and Built in's showcase this beautiful space in this historic home. On the grounds is also a Carriage House that used to make carriages back in the day. Oh the stories these walls could tell!!!

Sep. 2 – 9

$98 CAD per night