House holiday rentals in Middletown

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Top-rated house rentals in Middletown

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

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Guest favourite
A vibrant arcade room is showcased, featuring multiple classic and modern arcade games. Neon lighting enhances the playful atmosphere. An air hockey table occupies the foreground, while pinball machines and an arcade cabinet are visible in the background, contributing to a lively entertainment space.
Home in Kettering
4.91 out of 5 average rating, 107 reviews

Hot Tub Massage Pinball Stylish! By The Greene

Unwind in the Cedar Hottub Room or Massage chair. Have a blast with family and friends in or game room with brand-new Stern Pinball machines, Slot machines, Digital Putt-putt, Yard darts, cornhole, bowling, and arcade gaming systems. This house is a freshly remodeled home, everything is brand new. The outdoor Cedar room is a completely private area, romantic and relaxing. Literally 1 min drive from the Greene Outdoor Shopping Mall! You can expect a luxurious and super clean stay! GAMES ARE FREE

Top guest favourite
A modern living area features a dark gray couch adorned with colorful pillows, paired with a mid-century chair. Natural light enters through two windows, illuminating the stylish rug while a round mirror reflects the space. A flat-screen TV is mounted on the wall, accompanied by a decorative console.
Home in South Park
5 out of 5 average rating, 146 reviews

Modern Historic House in the heart of South Park

Check out this stylish and modern home in the Historic South Park District centrally located in Dayton Ohio. Located on the best street in this trendy neighborhood where you can enjoy a view of the park from the porch. Built in 1880 this newly revamped home has an open concept full kitchen, 2 bedrooms and 2 full baths. Wood flooring and 12-foot ceilings throughout. Close to downtown, Miami Valley Hospital and the University of Dayton. Within walking distance to shopping, dining and much more.

Top guest favourite
A welcoming front porch features a vibrant yellow door framed by comfortable seating on either side. Lush green bushes surround the entrance, and colorful flowers are planted along the steps leading to the home.
Home in Lebanon
4.87 out of 5 average rating, 248 reviews

Historic Lebanon Rustic Charm Experience

Rustic, historical two story home in downtown Lebanon, Ohio. Four blocks from the historical Golden Lamb Restaurant, walking distance to the boutiques and restaurants in Lebanon. 10 minutes from Kings Island, Miami Valley Gaming, Outlet Malls, Flea Markets, WC Sports Complex. Minutes away from many other attractions such as Valley Vineyard, Caesar's Creek, Little Miami Canoeing and the Ohio Renaissance Festival. We’re an hour from Columbus, 30 minutes from Dayton and 40 minutes from Cincinnati

Top guest favourite
An inviting upstairs area features two spacious twin beds with dark bedding against the backdrop of rustic wood paneling. A central rug with geometric patterns is positioned between the beds, while decorative wall hangings and a window provide natural light and charm.
Home in Lebanon
4.98 out of 5 average rating, 179 reviews

The Homespun Landing

Our newly renovated home was planned and decorated with YOU in mind! All of your home-away-from home needs will be met here! Our large upstairs area is our favorite spot to share! We know your kids will find this a very inviting get-away space! Our kitchen is full of all the things! We offer games, toys, foosball, AND a seven-seat hot tub out back! Enjoy coffee shops, restaurants, boutiques all within walking to Historical downtown Lebanon. We would love to be your new choice get-away!

Guest favourite
The living room features a comfortable sectional sofa paired with an oversized chair, accentuated by modern light fixtures. A round dining table is surrounded by four chairs. Large windows allow natural light to illuminate the space, enhancing the welcoming atmosphere.
Home in Milford
4.87 out of 5 average rating, 124 reviews

❤️ milford ⭐️ luxury cape cod home ⭐️

This is a 2 bedroom house,beautiful remodel with all the essentials. The 2 bedrooms each have a queen bed and a 12” Sealy mattress. Living room has a full sized sleeper sofa and oversized chair which pulls out to a twin bed. House includes sheets, towels, hair dryer, coffee makers, dishes, utensils, assorted glasses, starter paper products. Located .6 miles to Olde Milford and Little Miami bike trail, many shops and restaurants. Remote check in via keypad on front door No pets please

Top guest favourite
A cozy sitting area features a modern black fireplace adorned with decorative candles. Two brown leather chairs are positioned beside a wooden side table, with a small potted plant nearby. Natural light streams in through the windows, illuminating the elegant rug and neutral wall tones.
Home in Madisonville
4.95 out of 5 average rating, 118 reviews

Tranquil Oasis 2BR/2BA with King Bed & Coffee Bar

Escape to our charming 2-bedroom, 2-bathroom Airbnb located in the serene suburbs of Cincinnati! Our home offers comfortable beds, a pillow bar to choose from, two clean full bathrooms, and a fully stocked kitchen. Unwind in the cozy living space or sip your morning coffee from our fully stocked coffee bar. Just a short drive from downtown Cincinnati, our Airbnb provides easy access to local shops, restaurants, and attractions while offering a quiet respite from the city bustle

Top guest favourite
The entrance to the home is shown, featuring a welcoming porch with two rocking chairs and a decorative entry sign. A clean concrete path leads to the front door, and the surroundings include a landscaped area with gravel and a green lawn, alongside a white fence.
Home in Lebanon
4.97 out of 5 average rating, 102 reviews

Bungalow in Downtown Lebanon

Welcome to your newly renovated one-bedroom home! This chic retreat features a spacious king bed and a comfy pull-out couch with a mattress topper for extra coziness. The gleaming kitchen boasts brand-new appliances, perfect for culinary adventures. Step outside to your private back patio, complete with a Solo Stove for warm, relaxed evenings. Plus, enjoy the convenience of being within walking distance to the vibrant downtown scene. Your ideal home away from home awaits!

Top guest favourite
A cozy living area showcases two cream-colored couches positioned around a dark coffee table. Natural light enters through a large window, enhancing the space. A sleek ceiling fan is visible, and a small dining area is arranged with a table and two chairs against the wall.
Home in Miamisburg
4.95 out of 5 average rating, 187 reviews

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.

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
4.89 out of 5 average rating, 199 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!

Guest favourite
A living room is depicted with a television mounted on a wooden stand, flanked by two comfortable reclining chairs and a sectional sofa. An aviation-themed artwork hangs above, while a sleek, metal coffee table adds a modern touch. Natural light enters through windows with light blinds.
Home in Middletown
4.92 out of 5 average rating, 108 reviews

5 Minute Call

"5 Minute Call" is located next to the Middletown Regional Airport (home of ​Start Skydiving) and Smith Park. ​ The house is a 1 minute walk to the airport, 2 minute walk to Smith Park, 23 min drive to Spooky Nook, 29 min drive to Miami University Oxford. With an arcade set-up in the basement, large kitchen dining table, and theatre-like living room, the house has multiple rooms for gathering with friends and family.

Guest favourite
A dining area features a rustic wooden table set with a woven runner and a decorative vase containing fresh flowers. Surrounding it are four white, cushioned chairs. The space is brightened by natural light coming through large windows, with a cozy living area visible in the background.
Home in Dayton
4.93 out of 5 average rating, 209 reviews

Updated home in Dayton with low fees!

This unique home in Dayton is loaded with charm. It has been updated in all of the right places to maintain its original character while providing all of the amenities you desire. You'll get quartz countertops, new appliances, high-end mattresses, brand new wood bedframes, and a sit-in front porch. Whether you are here for work or play, this home will be a great "home away from home".

Superhost
A dining area is presented with a round table and four chairs, set with blue placemats and a glass centerpiece. A plush sofa and decorative artwork are visible in the adjacent living area, while a ceiling fan provides a comfortable ambiance throughout the space.
Home in Hamilton
4.92 out of 5 average rating, 125 reviews

Short walk to Spooky Nook & Main St./downtown area

Centrally located to the Hamilton area, we are only 2 short blocks away from the Spooky Nook Sports facility. Only a short drive(20 mins)to Miami University in Oxford for a visit with your student, and only mile to Main Street restaurant and entertainment DORA district. Come enjoy the many events and amenities now available in Hamilton on your visit.

Popular amenities for house rentals in Middletown

When is the best time to visit Middletown?

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Avg. price$133 SGD$131 SGD$143 SGD$176 SGD$172 SGD$174 SGD$225 SGD$212 SGD$189 SGD$154 SGD$151 SGD$139 SGD
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Quick stats about house rentals in Middletown

  • Total holiday rentals

    Explore 30 holiday rentals in Middletown

  • Nightly prices starting at

    Middletown holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,200 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 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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