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Holiday rentals in Middletown

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Top-rated holiday rentals in Middletown

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Top guest favourite
A light-colored couch is centered in the living area, complemented by a striped blue cushion. A glass coffee table rests on a patterned rug. A floor lamp and a side table fill the space, while a landscape painting adorns the wall, adding a touch of nature.
Flat in Centerville
4.9 out of 5 average rating, 351 reviews

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 third guest sleeps on a twin roll-away bed. The kitchen is equipped for basic cooking with a fridge, Keurig, oven, microwave and toaster plus tableware. 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. Free parking is available in the adjacent public lot.

Top guest favourite
Guest house in Lebanon
4.95 out of 5 average rating, 502 reviews

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

Guest favourite
The living area features wooden walls and a stone fireplace, complemented by soft-glow electronic candles. A cozy armchair is positioned near a window, while a round, textured coffee table sits at the center, adorned with a vase of dried flowers.
Guest house in Hamilton
4.98 out of 5 average rating, 254 reviews

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, or take a ride in the paddle boat, or simply enjoy sitting on the porch listening to the birds. Chances are, you may spot wild turkey or whitetail deer scampering by.

Top guest favourite
A spacious studio apartment is shown, featuring a king bed with soft linens, a comfortable seating area with a sectional sofa, and a wooden dresser. The kitchenette, equipped with wooden cabinetry and modern appliances, is visible in the background. Soft lighting enhances the welcoming atmosphere.
Guest house in Springboro
4.96 out of 5 average rating, 113 reviews

Comfortable Studio In Springboro

Welcome to a quiet, upscale golf course community within walking distance to Old Towne Springboro. Private 438 square foot studio apartment with a king bed, full bath, large kitchen and in unit washer and dryer. This guest suite has its own entrance that is accessed with a keypad. Location: Nestled in the Heatherwoode Golf Course community within walking distance to Old Towne Springboro and 10 min from Austin Landing. 15 minutes from Kings Island and Cincinnati Premium Outlets.

Superhost
Flat in Middletown
4.83 out of 5 average rating, 6 reviews

Beautiful NEW 2 Bedroom with FREE Laundry

This newly constructed two-bedroom apartment is part of a small complex in Middletown, Ohio. Live like a local with plenty of room for four to sleep comfortably in this unit. Close to I-75 and just an exit up from the Monroe Outlet Malls, there is plenty to do in this part of town! Relax on the comfortable sectional couch to watch TV on your favorite app, or grab a bite and sit at the bar table to eat! Great for small families or traveling workers. Hope to see you soon!

Top guest favourite
An inviting living area features a large brown leather sofa, a patterned area rug, and a decorative coffee table atop wide plank wood floors. A cozy corner chair and a lamp add warmth, while the back wall showcases a mural with 'Centerville Carriage.'
Guest house in Centerville
5 out of 5 average rating, 273 reviews

The Carriage House in the Heart of Uptown

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

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
4.9 out of 5 average rating, 234 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 modern two-story building is framed by lush greenery and mature trees, featuring a mix of dark wood and stone accents. Large windows provide natural light, while a curved pathway leads to the entrance, enhancing the inviting exterior.
Flat in Tipp City
4.91 out of 5 average rating, 240 reviews

Heartland - 2nd Floor Upper Level

Kick back and relax in this calm, stylish space. We invite you to exlore this hidden gem just outside of Tipp City, OH. Guests will enjoy a private bedroom, bathroom, kitchen, living area, and designated patio space all to themselves. Guests will enjoy the tranquil atmosphere and beautiful natural landscape with nearby biking or hiking trails. Grill out, make a fire, enjoy peaceful walk on the labyrinth and so much more.

Top guest favourite
The exterior of a single-story brick home is shown, featuring a double garage, manicured lawn, and flower beds with yellow blooming flowers. A driveway leads up to the home, surrounded by peaceful greenery and trees in the background.
Flat in Middletown
5 out of 5 average rating, 163 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.

Superhost
A spacious sleeping area features a padded headboard with a neatly made bed covered in a dark blanket. Two bedside tables with soft-lit lamps sit on either side, while a framed photograph of rocks hangs above the bed. Natural light enters through a window adorned with gray curtains.
Guest suite in Liberty Township
4.83 out of 5 average rating, 326 reviews

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

Top guest favourite
A cozy cottage exterior is framed by neatly trimmed shrubs and seasonal planters at the entrance. The house features a sloped roof with dark shingles and shutters. A stone pathway leads to a welcoming front door, complemented by subtle outdoor lighting along the walkway.
Home in Lebanon
5 out of 5 average rating, 102 reviews

Cozy Cottage with Gazebo Just off I71

Escape to our charming, pet-friendly Countryside Cottage for up to 6 guests! Near Kings Island & historic Lebanon, this cozy home is the perfect family getaway. Enjoy a relaxing massage chair, electric fireplace, a beautiful gazebo with a fire table, and a fully equipped kitchen. Experience a perfect blend of country peace and convenient access to local attractions.

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, 149 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 Middletown holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Middletown

Guest favourite
The kitchen features white cabinetry and a black countertop, complemented by a farmhouse sink. A decorative rug lies on the hardwood floor. A doorway leads to a dining area with a long wooden table, visible through the opening.
Home in Middletown
4.82 out of 5 average rating, 33 reviews

Quiet rustic retreat

Guest favourite
The exterior of a modern two-story home is presented, featuring a combination of white and dark blue siding. A prominent gabled roof and wooden accents frame the front door. A driveway leads to a two-car garage, and landscaping includes low bushes and a lawn.
Home in Middletown
4.96 out of 5 average rating, 45 reviews

NEWLY built sanctuary. Come make yourself at home!

Top guest favourite
A brown horse stands in a grassy field, surrounded by a white fence. Trees adorned with vibrant autumn leaves create a colorful backdrop, while other horses are seen grazing in the distance. The scene captures the serene atmosphere of the farm.
Farm stay in Lebanon
5 out of 5 average rating, 76 reviews

Farmhouse Stay

Top guest favourite
A historic two-story home with red wooden siding and contrasting black shutters is displayed. An American flag is mounted by the door, which is framed by a decorative wreath. Lush rose bushes and greenery surround the entryway, enhancing the charming exterior.
Home in Lebanon
4.98 out of 5 average rating, 97 reviews

Dwntwn Lebanon; 1st Floor., Historic, Washer/Dryer

Guest favourite
The living room features a brown tufted sofa paired with an orange accent chair. A white, sculptural coffee table is centered on a patterned area rug. Light streams in through two windows, with a dining area visible in the background, showcasing a simple table and chairs.
Home in Hamilton
4.9 out of 5 average rating, 79 reviews

FoosBall~SpookyNook~Theatre~GameRm~KingBD~Firepit

Top guest favourite
The living area features a comfortable gray sofa and an ornate armchair, complemented by large windows that allow natural light to illuminate the space. A fireplace, framed with decorative molding, adds character, while a mounted TV is positioned above the mantel. Light-colored curtains soften the room.
Flat in Hamilton
5 out of 5 average rating, 27 reviews

Riverfront Downtown Retreat

Top guest favourite
Home in Franklin
5 out of 5 average rating, 20 reviews

Franklin 4BR Retreat, Fenced Yard, No Airbnb Fees

Top guest favourite
Home in Hamilton
5 out of 5 average rating, 37 reviews

Westside Nook-5 Min Walk2Spooky

When is the best time to visit Middletown?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$165 SGD$170 SGD$137 SGD$169 SGD$191 SGD$196 SGD$223 SGD$232 SGD$205 SGD$207 SGD$183 SGD$160 SGD
Avg. temp-1°C0°C6°C12°C18°C23°C24°C24°C20°C13°C7°C1°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.

Quick stats about holiday rentals in Middletown

  • Total holiday rentals

    Explore 50 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 1,430 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 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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