Holiday Homes in Middletown

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Middletown

Our top choices for Middletown holiday homes

Pet-Friendly Dayton Home w/ Grill, Walk to Park!
Dishwasher, cookware/dishes/utensils

Pet-Friendly Dayton Home w/ Grill, Walk to Park!

10.0 out of 10, Exceptional, (44)
"The property was well maintained and quiet!"
Pet-Friendly Dayton Home w/ Grill, Walk to Park!
Happy Hen House 2-Bedroom House w/ Amazing Front Porch and Backyard Chickens
Interior

Happy Hen House 2-Bedroom House w/ Amazing Front Porch and Backyard Chickens

10.0 out of 10, Exceptional, (11)
"Was small, extremely cute house. Everything was very carefully thought out. We felt very comfortable there. Would definitely stay again. "
The price is AU$331
includes taxes & fees
25 Aug - 26 Aug
Happy Hen House 2-Bedroom House w/ Amazing Front Porch and Backyard Chickens
Enchanting Bungalow - 2BR Historic Hidden Gem
2 bedrooms, WiFi, bed sheets

Enchanting Bungalow - 2BR Historic Hidden Gem

9.8 out of 10, Exceptional, (14)
"We work with CSU and this is the best price for our team."
The price is AU$240
includes taxes & fees
3 Sept - 4 Sept
Enchanting Bungalow - 2BR Historic Hidden Gem
Canary Cottage in the Heart of MainStrasse Village
Smart TV

Canary Cottage in the Heart of MainStrasse Village

3.0 star property
9.6 out of 10, Exceptional, (23)
"Great location. Clean."
Canary Cottage in the Heart of MainStrasse Village
Dayton Family Home w/ Game Room: Walk to City Park
TV, fireplace

Dayton Family Home w/ Game Room: Walk to City Park

10.0 out of 10, Exceptional, (2)
"Our family had a wonderful stay. The house was exactly as shown, very clean, and we enjoyed the pool and game room very much. The manager was so helpful and quick to respond whenever we needed anything. Highly recommended home and host! "
Dayton Family Home w/ Game Room: Walk to City Park
Lovely house off Main Street
Fridge, microwave, oven, stovetop

Lovely house off Main Street

9.6 out of 10, Exceptional, (25)
"Everything was clean, parking was easy, cozy spot, great location. We would book again!"
The price is AU$365
includes taxes & fees
2 Sept - 3 Sept
Lovely house off Main Street
Beautiful Walnut Home 4bed/bathrooms with Private Parking
Fridge, microwave, oven, stovetop

Beautiful Walnut Home 4bed/bathrooms with Private Parking

9.6 out of 10, Exceptional, (25)
"Meticulously maintained home!"
Beautiful Walnut Home 4bed/bathrooms with Private Parking
Ohio Ave, 3 bed house, Historic Downtown Loveland
3 bedrooms, iron/ironing board, WiFi, bed sheets

Ohio Ave, 3 bed house, Historic Downtown Loveland

9.2 out of 10, Wonderful, (19)
"Clean and nice"
The price is AU$247
includes taxes & fees
27 Aug - 28 Aug
Ohio Ave, 3 bed house, Historic Downtown Loveland
The Poolside Escape
Pool

The Poolside Escape

8.0 out of 10, Very good, (2)
"Communication with host was great, very responsive as VRBO never sent any check in or check out instructions. Quiet street, easy to get to, pool was very nice and relaxing. Would recommend to anyone."
The price is AU$565
includes taxes & fees
9 Sept - 10 Sept
The Poolside Escape
NEW House of Liberty: 3BR 2BA w/ PRVT Hot Tub, Modern Patio, Amazing City Views
View from property

NEW House of Liberty: 3BR 2BA w/ PRVT Hot Tub, Modern Patio, Amazing City Views

8.6 out of 10, Excellent, (28)
"This was a great place and loved the views of the city. The only complaint I had was the master bedroom bed had crumbs on the comforter. "
The price is AU$575
includes taxes & fees
25 Aug - 26 Aug
NEW House of Liberty: 3BR 2BA w/ PRVT Hot Tub, Modern Patio, Amazing City Views
1 Bedroom, Luxury Loft
Fridge, microwave, oven, stovetop

1 Bedroom, Luxury Loft

8.4 out of 10, Very good, (12)
"The location of the property was excellent for locations"
The price is AU$305
includes taxes & fees
9 Sept - 10 Sept
1 Bedroom, Luxury Loft
Cozy and Comfortable w antique furnishings; 2 bedrooms, sitting area, full bath
Exterior detail

Cozy and Comfortable w antique furnishings; 2 bedrooms, sitting area, full bath

9.0 out of 10, Wonderful, (76)
"My mom and I were in town for Flying Pig. It poured rain the whole weekend so we were at the room more than we anticipated. The only opportunities I noticed were the tub could use a deep clean and the shower head pointed at the wall which made it difficult to have a proper shower. Beyond that, the location is amazing and it is such a quick drive into the city. My mom absolutely loved the place and wants to go back. "
Cozy and Comfortable w antique furnishings; 2 bedrooms, sitting area, full bath
Downtown skyline vista featuring giant rooftop deck & wet bar with a city view
Interior

Downtown skyline vista featuring giant rooftop deck & wet bar with a city view

10.0 out of 10, Exceptional, (11)
"Outstanding place for any stay in the area."
The price is AU$684
includes taxes & fees
8 Sept - 9 Sept
Downtown skyline vista featuring giant rooftop deck & wet bar with a city view
Suite Springs
Interior

Suite Springs

9.2 out of 10, Wonderful, (38)
"Tucked away in quite neighboorhood is this hidden gem! Suite is just as described and as photos show except the bedroom is larger than it looks! Comfortable bed , soft sheets and blankets. Hope to get to stay again!"
The price is AU$327
includes taxes & fees
26 Aug - 27 Aug
Suite Springs
2 BR, 1-1/2 bath house in wooded setting with private back yard, deck, hot tub.
Terrace/patio

2 BR, 1-1/2 bath house in wooded setting with private back yard, deck, hot tub.

10.0 out of 10, Exceptional, (107)
"Very nice property for relaxing!"
2 BR, 1-1/2 bath house in wooded setting with private back yard, deck, hot tub.
TOP Yellow Springs BnB+ Pet Friendly
Interior

TOP Yellow Springs BnB+ Pet Friendly

9.8 out of 10, Exceptional, (46)
"Loved it and recommend it to anyone staying in Yellow Springs, OH+"
The price is AU$1,136
includes taxes & fees
2 Sept - 3 Sept
TOP Yellow Springs BnB+ Pet Friendly
Beautiful Home in South Park. Walk to UD Campus, Miami Valley Hospital, Downtown
Fridge, microwave, oven, stovetop

Beautiful Home in South Park. Walk to UD Campus, Miami Valley Hospital, Downtown

9.0 out of 10, Wonderful, (54)
"We have stayed here a few times since our son started Dayton in the fall. We love the house, the location and our host Mike is extremely friendly and responsive. We will definitely be back!"
Beautiful Home in South Park. Walk to UD Campus, Miami Valley Hospital, Downtown
Luxury and Lavish Entire Home
Smart TV, fireplace, computer monitors

Luxury and Lavish Entire Home

2.0 star property
9.6 out of 10, Exceptional, (7)
"My stay was amazing. I would definitely recommend this booking to anyone who is looking for a weekend stay. "
Luxury and Lavish Entire Home
Love the Cov- Spacious 4-bedroom house in charming Covington with WiFi, AC
4 bedrooms, iron/ironing board, WiFi, bed sheets

Love the Cov- Spacious 4-bedroom house in charming Covington with WiFi, AC

9.6 out of 10, Exceptional, (5)
"Extremely tidy home! Highly recommend this house for a large group-especially if you have no trouble with stairs! Convenient to lots of dinner choices!"
Love the Cov- Spacious 4-bedroom house in charming Covington with WiFi, AC
Perfectly Small House
Exterior

Perfectly Small House

10.0 out of 10, Exceptional, (87)
"Host was so thoughtful! Perfect resting place during our weekend hiking trip."
Perfectly Small House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middletown Hotel Reviews

voco The Clair Cincinnati Downtown by IHG

voco The Clair Cincinnati Downtown by IHG

10/10 Excellent
"This was a great location. We were able to walk to different areas in the city. We could also get the free tram quite near the hotel. The room itself was clean and comfortable. There was a lot of space and the decor was appealing. Parking in the garage next door was super convenient."
Joan 3-night trip
Posted 2 hours ago
voco The Clair Cincinnati Downtown by IHG