Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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Guest favorite

Apartment in Franklin

4.9 out of 5 average rating, 143 reviews

Cozy Studio-Eat in Kitchen-5 min off I-75 Franklin

Enjoy a relaxing stay at this newly renovated studio apartment (sleeps up to 2) - Queen bed, full bath with tub, equipped kitchen with appliances, smart TV with high speed internet, and washer/dryer. This apartment is on a main street and within a 3 unit building (with separate entrances). It is located 2.1 miles off I75 (approx. 5 min) and close to The Little Miami Scenic Bike Path! Check in/out with key pad. Parking is close to apartment entrance in the driveway and behind the building.

Jul 31 – Aug 7

$78 per night

Guest favorite

Guesthouse in Loveland

4.98 out of 5 average rating, 483 reviews

Retreat to a Boho Chic Guesthouse in a Leafy Family Suburb

Get comfy swaying in the macrame hammock in a living room with a Moroccan vibe. Make breakfast in the bright kitchen and snuggle up on a cozy banquette. This guest house shares a driveway with our home, but it is completely detached and private. The bedroom sleeps two on a queen mattress, and we provide a queen sized inflatable mattress that fits easily in the living room. The property has a stocked kitchen, a washer and dryer, a lovely new bathroom, a two-car garage, and loads of aesthetic.

Nov 29 – Dec 6

$125 per night

Guest favorite

Guesthouse in Maineville

4.97 out of 5 average rating, 153 reviews

The Barn at Serenity Acre

Take it easy at this unique and tranquil getaway, where relaxation abounds. We are located in Warren county, the playground of Ohio. - total and complete renovation in 2021 - fully equipped kitchen - cozy bedroom / living room - spacious bathroom with claw foot tub to soak or shower in, vanity, and robes - walking trails in woods behind our property, access to pool (seasonal), close to restaurants, stores, vineyard, historic towns, very close to Kings Island, bike trails, and so much more

Apr 8 – 15

$122 per night

Guest favorite

Place to stay in Waynesville

4.97 out of 5 average rating, 195 reviews

Cozy private suite/Ohio to Erie/Miami Scenic Trail

Location is everything in this cozy accommodation catering to weekend guest and bicyclers on the Miami Erie Trail. Enjoy the quaintness of small town living in your one bedroom private cottage suite. You will have everything you need in this historic haven, made contemporary, for a relaxing stay. Walk to cafes, vintage shops, & drive a few minutes to Caesars Creek State Park & Rivers Edge Livery. Opt for breakfast on the go for an additional fee w/ homemade granola, protein and fresh fruits.

Jul 26 – Aug 2

$84 per night

Guest favorite

Cottage in Morrow

4.96 out of 5 average rating, 124 reviews

Rossburg Tavern (1800’s)

This house was built in the early 1800's as part of a small town "Rossburg" that no longer exists and is reported to have been a Tavern. This is one of the last remaining structures for this town along with the barn and house across the street. The house sits on one acre of land surrounded by farmland, so you'll have opportunity to relax by a campfire, enjoy the unique architecture of the house, or explore the wide variety of entertainment options all within 20 minutes of the house.

Nov 12 – 19

$100 per night

Guest favorite

Home in Middletown

4.88 out of 5 average rating, 113 reviews

Huge yard! 3-bedroom, 2 bath home right off I-75.

Enjoy our spacious master bedroom, brand new furniture, peaceful backyard with a 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! We care about our home and the guests that come to use it.

Jul 6 – 13

$141 per night

Guest favorite

Guesthouse in Fairborn

4.98 out of 5 average rating, 283 reviews

Cozy cabin at The Armstrong Homestead

The caretaker's cabin is a quaint one bedroom suite complete with a full bath, microwave, mini fridge and coffee. Off road parking and a secluded entry makes the cabin perfect for a romantic or working getaway. Located next to the Osborn Historic District in the heart of Fairborn, the Armstrong Homestead is an easy stroll to the downtown shops and restaurants. Xenia Dr provides direct access to the main highways, making most of Dayton reachable in 30 min or less.

Jan 19 – 26

$68 per night

Guest favorite

Apartment in Centerville

4.89 out of 5 average rating, 214 reviews

Cozy apartment in Centerville's Uptown District

This remodeled apartment is the twin to our popular Airbnb apartment located across the hallway. Two adults can sleep in a dedicated bedroom on a queen size bed and your child can sleep on an air mattress (the 2nd bed) in the living room. The kitchen is well-equipped with a stove, refrigerator, microwave, Keurig Coffee machine, toaster, & cooking basics. There's a smart TV, apple TV, and Alexa in the Living Room.

Nov 3 – 10

$67 per night

Guest favorite

Apartment in Middletown

5.0 out of 5 average rating, 105 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.

Dec 8 – 15

$95 per night

Guest favorite

Cottage in Hamilton

4.97 out of 5 average rating, 106 reviews

Four Mile Creek Cottage - Countryside Getaway

Relax and unwind with the whole family at this peaceful countryside getaway. Situated on 4 acres of woodlands greenery, directly overlooking Four Mile Creek, the cottage is tucked away from city noise yet super accessible: 5-minute drive to Spooky Nook Champion Mill and Downtown Hamilton, 15-minute drive to Miami University and Uptown Oxford, 50-minute drive to Cincinnati, 1-hour drive to Dayton, Ohio.

Apr 19 – 26

$151 per night

Guest favorite

Home in West Alexandria

4.9 out of 5 average rating, 238 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.

Feb 11 – 18

$81 per night

Guest favorite

Apartment in Hamilton

4.92 out of 5 average rating, 168 reviews

Charming 1 Bedroom Rental on Historic Dayton Lane

Take yourself back in time in this totally renovated 1884 Victorian Home. Original Parquet Wooden floors and Built in's showcase this beautiful space in this historic home. On the grounds is also a Carriage House that used to make carriages back in the day. Oh the stories these walls could tell!!!

Sep 2 – 9

$59 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Middletown vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Middletown's top sights

Start Skydiving5 locals recommend

Taco Bell5 locals recommend

Bourbon's Craft Kitchen and Bar3 locals recommend

Other great vacation rentals in Middletown

Guest favorite

Apartment in Milford

4.94 out of 5 average rating, 409 reviews

One Bedroom Apt in Historic, Downtown Milford

Aug 19 – 26

$90 per night

Guest favorite

Cottage in Dayton

4.98 out of 5 average rating, 257 reviews

The Blue Heron Guest House

Dec 14 – 21

$108 per night

Guest favorite

Guest suite in Dayton

4.94 out of 5 average rating, 142 reviews

The Wayside

Aug 11 – 18

$79 per night

Superhost

Home in Liberty Township

4.85 out of 5 average rating, 191 reviews

Suburban Sanctuary! Close to Cin and Day.

May 28 – Jun 4

$134 per night

Guest favorite

Apartment in Miamisburg

4.88 out of 5 average rating, 194 reviews

1 Bdrm Apt by Brewery Bike & River

May 6 – 13

$88 per night

Guest favorite

Home in Middletown

4.87 out of 5 average rating, 46 reviews

5 Minute Call

Jan 24 – 31

$101 per night

Guest favorite

Home in Middletown

4.86 out of 5 average rating, 22 reviews

Stanley Cozyside

Mar 16 – 23

$113 per night

Guest favorite

Home in Germantown

5.0 out of 5 average rating, 22 reviews

The FarmTown Bungalow

Mar 30 – Apr 6

$90 per night

Show all

Quick stats about vacation rentals in Middletown

Total rentals
60 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
910 reviews
Nightly prices starting at
$20 before taxes and fees

Frequently Asked Questions

Are there family-friendly vacation rentals in Middletown?
Middletown has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Middletown have free parking?
Absolutely! We offer over 20 apartment rentals with free parking in Middletown. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Middletown have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Middletown. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Middletown?
Experience the best of Middletown with our house rentals, starting at about $20 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 50 vacation rentals in Oakland, over 10 vacation rentals in Avalon, and over 50 vacation rentals in Mayfield.
Are there vacation rentals with a dedicated workspace in Middletown?
Yes! Work meets play with ease at over 30 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 house rentals in Middletown have wifi?
Absolutely! We offer over 30 house rentals with wifi in Middletown. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Middletown have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Middletown. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Middletown?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 homes with wifi, over 20 homes with a kitchen, over 30 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Middletown

Top-rated vacation rentals in Middletown

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Middletown vacation rentals

Stay near Middletown's top sights

Other great vacation rentals in Middletown

Apartment in Milford

Cottage in Dayton

Guest suite in Dayton

Home in Liberty Township

Apartment in Miamisburg

Home in Middletown

Home in Middletown

Home in Germantown

Quick stats about vacation rentals in Middletown

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there family-friendly vacation rentals in Middletown?

Do apartment rentals in Middletown have free parking?

Do house rentals in Middletown have air conditioning?

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

Where should I stay in Middletown?

Are there vacation rentals with a dedicated workspace in Middletown?

Are there pet-friendly vacation rentals in Middletown?

Do house rentals in Middletown have wifi?

Do apartment rentals in Middletown have a kitchen?

What are the most popular amenities for House Rentals in Middletown?

Destinations to explore