Holiday rentals in Middletown

Guest house in New Lebanon

4.97 out of 5 average rating, 203 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.

4.96 out of 5 average rating, 141 reviews

Flat in Lewisburg

Leader Loft

Conveniently located less than a mile from I-70 exit 14, on State Highway 503. This loft is perfect for any stay length for every occasion, and with the electronic door lock system it is perfect for a last minute stop as you’re traveling down the interstate. The Loft shares our building with Flour Bakery, coffee and gift shop, and is a minute's walk from a delicious bistro, antique shops, other gift shops, the library and hardware store. Come explore all that our quaint village has to offer!

4.9 out of 5 average rating, 286 reviews

Flat in Centerville

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 house in Maineville

4.96 out of 5 average rating, 220 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

4.99 out of 5 average rating, 209 reviews

Guest house in Hamilton

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.

4.95 out of 5 average rating, 424 reviews

Guest house in Lebanon

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

4.96 out of 5 average rating, 157 reviews

Home in Miamisburg

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 house in Centerville

5 out of 5 average rating, 195 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, romantic get away, 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.

4.9 out of 5 average rating, 178 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!

5 out of 5 average rating, 138 reviews

Flat in Middletown

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.

4.97 out of 5 average rating, 152 reviews

Cottage in Hamilton

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.

4.95 out of 5 average rating, 180 reviews

Home in Belmont

Updated home in Dayton with low fees!

This unique home in Dayton is loaded with charm. It has been updated in all of the right places to maintain its original character while providing all of the amenities you desire. You'll get quartz countertops, new appliances, high-end mattresses, brand new wood bedframes, and a sit-in front porch. Whether you are here for work or play, this home will be a great "home away from home".

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Popular amenities for Middletown holiday rentals

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Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Middletown

Superhost

4.67 out of 5 average rating, 9 reviews

Quiet rustic retreat

GiaoRating, 5 stars3 weeks ago

One of the best airbnbs i have ever stayed at. My family was visiting from Vietnam and they had a really great stay!

4.89 out of 5 average rating, 38 reviews

Stanley Cozyside

BryanRating, 5 stars1 month ago

Stayed here a few days for my daughter’s basketball tournament. The hosts were very good communicators and responded to all of my questions in a very timely manner. The place itself was beautiful, extremely clean, great furnishings, and super comfy beds. If I am ever up in this area again, I will definitely stay here.

4.98 out of 5 average rating, 64 reviews

Flat in Monroe

Renovated 2Bed/1 Bath with King Bed. Pets Welcomed

RebeccaRating, 5 stars1 week ago

We came to Dawn’s place to stay for our two day trip to Kings Island. We wanted to bring our two kitties with us. Her place was pet friendly. She was very accommodating to us having our pets with us. She offered blankets to cover the furniture. She also waived the pet cleaning fee as long as we cleaned up after our pets. Toiletries were provided as well as coffee and all kitchen supplies. She was quick to respond to any questions we had. Thank you Dawn! This was the perfect home away from home! We would definitely stay again.

5 out of 5 average rating, 52 reviews

Home in Lebanon

Walkable on E. Warren St.

AnaRating, 5 stars1 week ago

We stayed at Grant and Rachel’s during a lacrosse tournament. Easy walk to downtown Lebanon and ten minutes from the tournament location. They provided us with very clear instructions regarding check in and parking. The house looked exactly like the pictures. Plenty of linens and towels exactly where the instructions said they would be. You can tell they put a lot of thought into the place. Beds were very comfortable, including trundle and sofa bed. Very clean. We appreciated the camp chairs in the laundry room as we forgot to bring ours. We would definitely stay again.

5 out of 5 average rating, 49 reviews

Home in Oregon

Luxury Oregon District Home - Heated Pool (OPEN)

XochilRating, 5 stars2 weeks ago

Very beautiful home with plenty of space. The outdoor heated pool was a big hit and my family had so much fun! I would definitely recommend this place.

4.95 out of 5 average rating, 22 reviews

Cozy, Cute & Clean Home

ChristinaRating, 5 stars1 month ago

Great place, very cute and clean! We appreciated the drinks and restaurant recommendations.

Superhost

4.83 out of 5 average rating, 12 reviews

Cute Ranch home Middletown, OH

AnzaRating, 5 stars3 weeks ago

Jason’s place was great! We had a last minute flight cancellation and he was flexible to help get us reschedule. Great location for kiddos right down from the park. Clean and comfortable!

Superhost