
House holiday rentals in Middletown
Find and book unique houses on Airbnb
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 $65 SGD per night before taxes and fees

Verified guest reviews
Over 1,170 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!
Top-rated house rentals in Middletown
Guests agree: these houses are highly rated for location, cleanliness and more.

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!

General Mitchel Historic Home in Downtown Lebanon
Ormsby Mitchel was a Major General during the Civil War, and this was his home. This updated historic home was built in 1814 and is in the heart of downtown Lebanon. Local shops and restaurants are within walking distance. Easy access to local attractions like Kings Island and the Miami Valley Casino. We offer 3 bedrooms, 2 full baths, and plenty of space to spread out. A charming place to stay when traveling for work, a romantic weekend, a getaway with friends, or a family gathering.

Luxury & Wellness
Discover a sanctuary of wellness and luxury in the heart of Dayton, Ohio. Our exclusive three-bedroom, two-bath home is not just a place to stay, it's an immersive bio-hacking experience designed to rejuvenate your mind, body, and soul. Here, health technology isn't just an amenity, it's a way of life offered to our guests at no extra cost. You have seen celebrities like Joe Rogan embrace these technologies on social media, and now it's your turn to experience their transformative power.

Walking distance to shops, dining, and fun
Bring the entire family and stay with us. We have 4 bedrooms 3 bathrooms, multiple gathering spaces, front porch, back deck with outdoor dining, game room, and the home is handicap friendly with a ramp to the first floor which includes a bedroom and a full bathroom. With our multiple gathering spaces and large bedrooms, you will have plenty of space to spread out or hang out together. We are just minutes from shopping, restaurants, entertainment, and the Spooky Nook Sports Complex.

Charming renovated historic home in ideal location
Location, Location, Location!! Nestled in the idyllic Rossville Historical District, this property is a block away from Main Street and within walking distance to many restaurants, shops and downtown Hamilton. Whether you’re coming in town for Miami University, Spooky Nook Sports Complex, work, family, or just a weekend getaway, you’ll find that this property is the perfect spot to stay. Enjoy a completely renovated property with all new furnishings in a historic 1800’s home.

4-Beds: Firepit / Game Consoles / Workstation
Please see other notes for rules / disclaimers. Half a mile from Spooky Nook & blocks away from the new Agav & Rye. At 'The Sunset Nook', we have taken every effort to add every amenity possible to make a perfect experience. One block away from Sutherland family Park (See Pics). Our home is surrounded by landscape lighting to create a relaxing/secure environment. Our guest comfort and security is a top priority; spotlight/security cameras monitor the property for guests.

Walk to Downtown Loveland, Porch, Fire Pit, Coffee
DISCOUNT for multiple nights (not including Airbnb's service fee) & $0 Cleaning fee Includes: - coffee bar - smart TV, board games - screened porch - free private parking - patio with lights and fire pit - secured bicycle storage available in garage - corn hole set Walking distance (5 minutes) to revitalized Historic Downtown Loveland and Little Miami Bike Trail. Restaurants, Canoe/Kayak Rental, Park/Playground, Bike Rentals. Close to Kings Island and Tennis Venue.

Backwoods Hideaway|NEW BUILD2024
The Backwoods hideaway provides the perfect escape for a family or just a couple looking to get away! Located on a 75 acre farm between Cincinnati & Dayton, and only 8 miles from Oxford! Boasts an impressive open floor plan & an expansive open patio overseeing the woods! Unwind at the luxury 3 bed room , with a loft & 2 full size beds for the kids, and 2 bathroom vacation home with the most amazing sunset views!! Guests will have access to the entire home!

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.

StayStonybrook - Fairfield Township
Spacious 4BR / 2BA Home in Fairfield Township—perfect for families, groups, and extended stays. Enjoy a huge backyard, pet-friendly comfort, and plenty of room to relax after a day of exploring. Sleeping Arrangements • King bedroom • Queen bedroom • Full bedroom • Twin bedroom with desk (great for work or kids) ✔ Two full bathrooms ✔ Large, fenced backyard ✔ Less than 20 minutes to Kings Island Comfort, space, and convenience—all in one stay.

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!
Popular amenities for house rentals in Middletown
House rentals with a pool

Nick's Covington Resort

Barefoot Tiki Retreat - Pool/Firepit/Game Room

Downtown Walnut Street Lawrenceburg - Heartbeat

Unique Luxury Family Retreat

Gorgeous Lake House with Pool - Stone Haven

Kingston Cottage Retreat

New Inground Pool! Pet Friendly with fenced yard.

Huber Heights Hot Tub Bungalo
Weekly house rentals

Historic Midcentury Lustron Home

NEWLY built sanctuary. Come make yourself at home!

Walkable on E. Warren St.

Stay and Play / Close to Kings Island and GWL

Beautiful Home: Near WSU/UD/WPAFB/ M.V. Hospital.

The Storms House

Pleasant Dreams - Hamilton, spooky Nook, Miami Unv

Franklin 4BR Retreat, Fenced Yard, No Airbnb Fees
Private house rentals

Home w/ King Bed & Fire pit centrally located

Quiet rustic retreat

Happy Place Haven!

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

Tiny Home fit for a King: Near Belmont Park!

1895 meets 2025 Townhouse

Freshly Remodeled! The Carnation House

Modern Milford Getaway-Near Cincinnati •Sleeps 6
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $138 SGD | $133 SGD | $149 SGD | $174 SGD | $170 SGD | $173 SGD | $223 SGD | $210 SGD | $187 SGD | $185 SGD | $172 SGD | $143 SGD |
| Avg. temp | -1°C | 0°C | 6°C | 12°C | 18°C | 23°C | 24°C | 24°C | 20°C | 13°C | 7°C | 1°C |
Destinations to explore
- Nashville Holiday rentals
- Chicago Holiday rentals
- Sevierville Holiday rentals
- Gatlinburg Holiday rentals
- Pigeon Forge Holiday rentals
- Indianapolis Holiday rentals
- Pittsburgh Holiday rentals
- Columbus Holiday rentals
- Asheville Holiday rentals
- Cleveland Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Kings Island
- Great American Ball Park
- Creation Museum
- Cincinnati Zoo & Botanical Garden
- Perfect North Slopes
- Cincinnati Music Hall
- Newport Aquarium
- Paycor Stadium
- University of Cincinnati
- John Bryan State Park
- Duke Energy Convention Center
- University of Dayton
- Cincinnati Art Museum
- Xavier University
- Heritage Bank Center
- Smale Riverfront Park
- Hard Rock Casino Cincinnati
- Big Bone Lick State Historic Site
- Jungle Jim's International Market
- TQL Stadium
- National Underground Railroad Freedom Center
- Eden Park
- Contemporary Arts Center
- Krohn Conservatory





