Places to stay in Middletown

Book unique places to stay, houses, and more on Airbnb

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Popular amenities for Middletown places to stay

Stay near Middletown's top sights

Taco Bell5 locals recommend
Combs BBQ Central4 locals recommend
The Pendleton Art Center Middletown3 locals recommend
Triple Moon Coffee Company3 locals recommend
Bourbon's Craft Kitchen and Bar3 locals recommend
West Central Wine3 locals recommend

Other great vacation rentals in Middletown

Top guest favorite
Home in New Carlisle
4.99 out of 5 average rating, 121 reviews

Beautiful 6-BR home in the country. TV and Wifi

BethRating, 5 stars1 month ago
Carol’s place was exactly as described. The home was very large, and had plenty of space to spread out. We had a large group of all ages, and everyone had somewhere to sleep safely. I liked that there were two bedrooms downstairs, so there was enough accommodations for the people in our group that couldn’t safely do the stairs. I imagine it would be fun to stay in summertime when you could enjoy the outdoors as well! This will be our go to place for the Dayton area!
Top guest favorite
Guesthouse in New Lebanon
4.97 out of 5 average rating, 194 reviews

Cottage on a working market garden

KeithRating, 5 stars1 week ago
I stayed here for a week of work. Easy drive to Moraine. The cottage was perfect, and had everything I needed. Zella was a gracious hostess, and gave me some homemade cookies for my travel home. I have to travel for work here again in a couple months. I hope there will be availability, so I can stay again!
Top guest favorite
Home in Dayton
4.97 out of 5 average rating, 274 reviews

Spacious 4BR/3.5BA Home Near UD, Oregon &DT Dayton

JanetRating, 5 stars3 weeks ago
Mayra's place was beautiful! It had plenty of space for our group of friends. We really appreciated that there were so many bedrooms and bathrooms. We hope to stay again!
Top guest favorite
Home in Hamilton
4.92 out of 5 average rating, 48 reviews

*Big home with pool-Spooky Nook*

BelnerRating, 5 stars5 days ago
Tyianna was a fantastic host. Communication was smooth and timely, which made everything easy from the start. The location was perfect for everything we needed to do, and the house itself felt just like home. My family kept saying how comfortable and welcoming it was. Would definitely stay again!
Top guest favorite
Home in Oakley
4.99 out of 5 average rating, 117 reviews

Oakley Gold Std: New Construc/4king bed/4ens bthrm

MorganRating, 5 stars2 weeks ago
Well wiped, clean and large spaces. A high quality Airbnb.
Guest favorite
Guest suite in Edgewood
4.88 out of 5 average rating, 279 reviews

Mod Lodge Close to Cinci Creation museum and Ark

AubriannaRating, 5 stars2 weeks ago
Monica and her Airbnb were fantastic! The place was very nice and clean, and we really appreciated how well-stocked it was - there was so much attention to detail and thoughtfulness. Monica was also responsive and readily available - we had issues navigating the keypad upon returning around midnight, and I felt SO bad reaching out for help but she messaged back right away and arrived within minutes to get us inside.
Guest favorite
Apartment in Over-The Rhine
5 out of 5 average rating, 17 reviews

Let’s get away to a Hide Away!

JoshuaRating, 5 stars5 months ago
Spent my birthday at the property! Lelia took great care of us and the space was awesome. We plan to come back!
Top guest favorite
Home in Hebron
4.99 out of 5 average rating, 147 reviews

Spacious home with lots of family entertainment

TravisRating, 5 stars1 month ago
This is the second time staying in Sara‘s place. Honestly I will never stay anywhere else when visiting the Hebron/Florence area. Her home is so well appointed and so clean and taken care of it truly has become our home away from home when visiting family here. It is definitely worth the money to stay in this beautiful home. I highly recommend it.

Quick stats about vacation rentals in Middletown

  • Total rentals

    70 properties

  • Nightly prices starting at

    ﺩ.ﺇ73 before taxes and fees

  • Total number of reviews

    1.4K 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

  • 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 Oakland, over 60 vacation rentals in Mayfield, and over 10 vacation rentals in Avalon.

  • 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.

  • Are there apartment rentals with a dedicated workspace in Middletown?

    Yes! Work meets play with ease at over 10 apartment rentals in Middletown featuring dedicated workspaces. Stay connected and productive in your home away from home.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with self check-in, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there pet-friendly house rentals in Middletown?

    Four-legged friends are welcome in Middletown. Choose from more than 10 house 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 house rentals in Middletown have self check-in?

    Absolutely! We offer over 10 house rentals with self check-in in Middletown. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly apartment rentals in Middletown?

    Middletown has more than 20 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

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