Are there family-friendly vacation rentals in Middletown?

Middletown has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

How much does it cost to stay in apartment rentals in Middletown?

Experience the best of Middletown with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Where should I stay in Middletown?

Make yourself at home in Middletown by choosing from our most frequently booked neighborhoods. We have over 60 vacation rentals in Mayfield, over 10 vacation rentals in Avalon, and over 60 vacation rentals in Oakland.

Are there vacation rentals with a dedicated workspace in Middletown?

Yes! Work meets play with ease at over 40 vacation rentals in Middletown featuring dedicated workspaces. Stay connected and productive in your home away from home.

Are there pet-friendly vacation rentals in Middletown?

Four-legged friends are welcome in Middletown. Choose from more than 10 vacation rentals for guests traveling with pets.

Do apartment rentals in Middletown have wifi?

Absolutely! We offer over 20 apartment rentals with wifi in Middletown. Enjoy a tailored experience with all the comforts you desire.

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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Top guest favorite

Guesthouse in New Lebanon

4.97 out of 5 average rating, 209 reviews

Cottage on a working market garden

Studio cottage with full bath and self-catering kitchen with pots and pans, etc., queen sized bed with fresh linens and towels provided. This cottage is on a working market garden. Maximum occupancy two adults. We do have a small bed that could be added to accommodate a small child about 6 years and under. WE WILL ACCEPT SOME PETS, BUT NOT ALL. We are one mile from grocery shopping. Local roads ideal for cycling. Thirteen miles west of Dayton. Price includes fresh flowers and vegetables from the garden during the season. One cat on the property. Cottage has ceiling fan and good air circulation and a window air-conditioner during the warmer months. There is a TV that streams Apple TV and Kanopy in the cottage, and excellent WIFI access. National Air Force Museum in Dayton is only 20 miles/ 30 minutes away. University of Dayton is 14 miles/ 20 minutes from the cottage. Dayton International Airport is 21 miles/ 26 minutes away. Your hosts are a hospitable couple who enjoy meeting new people. If no one else is booked after you, we can be more flexible with the check-out time.

Guest favorite

Apartment in Centerville

4.89 out of 5 average rating, 291 reviews

Apt 1: Octopus Garden in Uptown Centerville

This apartment is a twin to our Apt 2: Pilot Lounge located across the hall. Two adults can sleep in a dedicated bedroom on a queen bed while your child sleeps on an air mattress (the 2nd bed) in the living room. The kitchen is equipped for basic cooking with a fridge, Keurig, oven, microwave and toaster. 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. Parking is available in the adjacent public lot

Guest favorite

Apartment in Dayton

4.91 out of 5 average rating, 136 reviews

Studio Neutral Chic near Kettering Hospital & Shop

Come enjoy this quaint unit in Kettering...close to shopping, restaurants, hospitals and city attractions! King size bed, balcony and tranquil essential oil diffuser will help set the mood and relax you during your stay! Walk or drive to various local and chain restaurants. 9 min drive to Kettering Hospital (main campus)...5 minute drive to The Greene Towne Centre. Visit Downtown Dayton/ Oregon District within 15 minutes. Hike Clifton Gorge in Yellow Springs within 30 min. 3 minute walk to pub

Top guest favorite

Guesthouse in Hamilton

4.99 out of 5 average rating, 214 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 favorite

Guest suite in Liberty Township

4.98 out of 5 average rating, 105 reviews

Suite Liberty – Clean/Spacious

Our lower level, walk out suite (private entrance) has all you are looking for & more. The 1000 sf plus suite is spacious & comfortable. We are located on 2 peaceful acres in a residential area near the Liberty Way Exit off I-75. In our suite the focus is on cleanliness and functionality. Our sheets, towels & linens are laundered in Free & Clear products. For your comfort and security, the home is equipped with a Whole House Generator & Security Cameras on the outside.

Top guest favorite

Apartment in Monroe

4.98 out of 5 average rating, 136 reviews

Newly Remodeled Two Bedroom rental unit

Newly Remodeled, Pet Friendly, King & Queen Beds, Washer&Dryer in unit, Smart TV's in every room, Alexa, Keyless Entry. For children: high chairs, Pack and Play's with thick mattresses, Air Mattress. 2 miles from I-75, Close to Kings Island, Miami Valley Gaming Casino, Flea Markets, Premium Outlet Mall, Centrally located between Dayton and Cincinnati, 30 minutes to Cincinnati Reds, Bengals, Dayton Dragons. Close to Lebanon Sports Complex & Warren County Sports Park

Guest favorite

Guesthouse in Lebanon

4.95 out of 5 average rating, 429 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. 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

Top guest favorite

Home in Miamisburg

4.95 out of 5 average rating, 163 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 favorite

Home in Middletown

4.89 out of 5 average rating, 187 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 favorite

Guesthouse in Centerville

5 out of 5 average rating, 208 reviews

The Carriage House in Historic Uptown Centerville

Welcome to the Carriage House. Walk to shops, restaurants, ice cream & more! Whether you're staying for a fun weekend, work or visiting family and friends- the Carriage House is the perfect place. The Carriage House was built in 1897 & underwent a complete renovation in 2017. With its open style concept & 12 ft ceilings, it has taken on a whole new role as one of Centerville's coziest getaways, in the heart of Uptown.

Top guest favorite

Apartment in Middletown

5 out of 5 average rating, 140 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.

Guest favorite

Guest suite in Liberty Township

4.84 out of 5 average rating, 259 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

Vacation rentals for every style

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Popular amenities for Middletown vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Middletown

Home in Middletown

4.64 out of 5 average rating, 14 reviews

Quiet rustic retreat

Top guest favorite

Farm stay in Lebanon

5 out of 5 average rating, 56 reviews

Farmhouse Stay

Guest favorite

Apartment in Hamilton

4.97 out of 5 average rating, 38 reviews

Charming 1 bedroom at the Alamo

Guest favorite

Apartment in Franklin

5 out of 5 average rating, 5 reviews

Cozy Retreat Washer/Dryer Inside

Top guest favorite

Apartment in Hamilton

5 out of 5 average rating, 5 reviews

Heart of Hamilton #6- Spooky Nook, Miami U

Top guest favorite

Private room in Hamilton

4.94 out of 5 average rating, 117 reviews

Queen City Airbnb/Entire Basement/Private Entrance

Guest favorite

Private room in Liberty Township

4.87 out of 5 average rating, 139 reviews

Charming guest rooms in countrylike setting.

Top guest favorite

Guest suite in Hamilton

5 out of 5 average rating, 55 reviews

Quiet oasis located near Spooky Nook, Miami Univ.

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Quick stats about vacation rentals in Middletown

Total rentals
80 properties
Nightly prices starting at
G$4,180 GYD before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace

Frequently Asked Questions

Are there family-friendly vacation rentals in Middletown?
Middletown has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in apartment rentals in Middletown?
Experience the best of Middletown with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Where should I stay in Middletown?
Make yourself at home in Middletown by choosing from our most frequently booked neighborhoods. We have over 60 vacation rentals in Mayfield, over 10 vacation rentals in Avalon, and over 60 vacation rentals in Oakland.
Are there vacation rentals with a dedicated workspace in Middletown?
Yes! Work meets play with ease at over 40 vacation rentals in Middletown featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Middletown?
Four-legged friends are welcome in Middletown. Choose from more than 10 vacation rentals for guests traveling with pets.
Do apartment rentals in Middletown have wifi?
Absolutely! We offer over 20 apartment rentals with wifi in Middletown. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Middletown

Top-rated vacation rentals in Middletown

Vacation rentals for every style

Popular amenities for Middletown vacation rentals

Other great vacation rentals in Middletown

Quick stats about vacation rentals in Middletown

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with dedicated workspaces

Frequently Asked Questions

Destinations to explore