House holiday rentals in Middletown

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Top-rated house rentals in Middletown

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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, 178 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
A cozy living area features a plush sofa facing a flat-screen TV mounted above a decorative fireplace. A wooden coffee table sits upon a patterned area rug, while a recliner is positioned nearby. Natural light enters through the window, illuminating the neutral-toned walls.
Home in Hamilton
4.98 out of 5 average rating, 102 reviews

3 blocks from Spookynook & on the historical reg.

Steps away from Main Street, this property is close to everything making it easy to plan your visit. It's located on one of Hamilton’s most beautiful streets in the Rossville Historic District, is one of the oldest rental properties in the county, and is the on the historic registry. However, the unit is completely remodeled and updated with stainless steel appliances, subway tiled kitchen, ceramic tile shower surround, and laminate vinyl plank throughout. A cool, quaint place!

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.

Top guest favourite
A spacious living area is characterized by soft blue walls and ample natural light from large windows. A light-colored sofa with decorative pillows faces a central coffee table, while a fireplace is framed by built-in shelves displaying books and decor.
Home in Hamilton
4.95 out of 5 average rating, 133 reviews

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!

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, 198 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!

Top guest favourite
Home in Dayton
4.95 out of 5 average rating, 195 reviews

Beautiful Design, King Bed. Near it All. Fast Wifi

Welcome to La Belle Verde, a Guest Favorite in Dayton’s Historic St. Anne’s Hill. Built in the late 1890s, this home rests on a quiet, tree-lined street in one of Dayton’s most historic neighborhoods, it’s only minutes from downtown, the Oregon District, UD, and Miami Valley Hospital. Inside, history and comfort come together in 10-foot ceilings, windows that pour in natural light, and greenery that brings the home to life.

Guest favourite
The arcade room features a pool table at the center, illuminated by vibrant blue lighting. Walls are adorned with vintage pinball machines and classic arcade cabinets. A bar area with stools is visible in the corner, enhancing the space's playful atmosphere.
Home in Dayton
4.97 out of 5 average rating, 133 reviews

Hot Tub Sauna Golden Tee Pinball Stylish!

Relax in Style at Our Spacious Entertainment Retreat The space comfortably sleeps up to 6 guests, with two king-size beds and a Queen Bed. Unwind after a long day in our luxurious Hot Tub or rejuvenate in the sauna. Enjoy endless fun in the fully equipped game room with brand-new pinball machines, a pool table, slot machines, Golden Tee, and a Multicade arcade system with over 5,000 games — all free to play!

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".

Guest favourite
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.

Top guest favourite
The living area features a combination of retro-style seating, including a green futon and rattan furniture. A coffee table is centered on a plush white rug, while a large window allows natural light to illuminate the space. Decorative elements can be seen on the walls.
Home in West Alexandria
4.91 out of 5 average rating, 286 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.

Guest favourite
A comfortable living area is presented, featuring a spacious sectional sofa and a large flat-screen television positioned on a wooden media console. Natural light enters through two windows, softened by white curtains. A patterned rug covers the floor, and a potted plant adds a touch of greenery.
Home in Hamilton
4.85 out of 5 average rating, 124 reviews

StayStonybrook - Fairfield Township

Awesome 4 Bedroom | 2 Full Bath House | Huge Backyard | Pet Friendly Located in Fairfield Twp, OH | This 4 Bedroom, 2 Full Bath is the perfect spot for a family get away. Bedroom Layout: - King Size Room - Queen Size Room - Full Size Room - Twin Room w/ Desk 2 FULL Baths! Large Backyard! Less than 20 Minutes from Kings Island!

Guest favourite
A well-appointed kitchen and living area is showcased, featuring a black sectional sofa with a soft throw. Light wood flooring complements the white cabinetry and modern appliances, including a microwave and a stove. A stylish wall featuring intricate tile patterns adds character.
Home in Dayton
4.91 out of 5 average rating, 140 reviews

Petite Paradise: Tiny Home Vibes! Great Location!

Tiny Home! Enjoy 420 sq home, a private fenced-in yard for your furry friends! Relax on the spacious sun deck or take advantage of the large side yard—ideal for running and playing with your dog. Plus, unwind by the cozy fire pit with provided wood and a swing for ultimate relaxation. Perfect for pet owners and nature lovers alike!

Popular amenities for house rentals in Middletown

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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 £15 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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