Default HTG hotel image

Middletown Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Middletown holiday rentals

A kitchen with a brick wall, wooden shelves, a coffee maker, a sink, and a clock.

1. The Exchange - A Historic Downtown Studio

The Exchange - A Historic Downtown Studio
Owosso
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful host and property. Well appointed and nice kitchenette with coffee and espresso machine…bonus points for that!"
United States
Eric K.
The price is HK$1,012
HK$1,169 total
includes taxes & fees
5 Oct - 6 Oct
The Exchange - A Historic Downtown Studio
A spacious dining area with a wooden table and chairs, a bench with a patterned cushion, and a large window providing a view of greenery outside.

2. Spacious Downtown Owosso Loft

Spacious Downtown Owosso Loft
Owosso
9.8 out of 10, Exceptional, (53 reviews)
"Great location for the Shi-Tri"
United States
Kathleen S.
The price is HK$824
HK$1,603 total
includes taxes & fees
5 Oct - 6 Oct
Spacious Downtown Owosso Loft
A kitchen with a central island, wooden cabinets, and a chandelier.

3. The Finley Block

The Finley Block
3.5 star property
Owosso
8.4 out of 10, Very good, (65 reviews)
"good place to stay"
United States
Sanjay
The price is HK$770
HK$934 total
includes taxes & fees
19 Oct - 20 Oct
The Finley Block
A brick building with a black front door, a small porch, and a mailbox labeled "POST".

4. Historic 2-bedroom condo in Owosso

Historic 2-bedroom condo in Owosso
Owosso
9.8 out of 10, Exceptional, (10 reviews)
"Highly recommend this home! It's located in a prime location, beautifully decorated a d feels like home!"
United States
Daniel S.
The price is HK$1,130
HK$1,918 total
includes taxes & fees
8 Oct - 9 Oct
Historic 2-bedroom condo in Owosso
A spacious living area with a large L-shaped sectional sofa, a round coffee table, and a dining area with a wooden table and chairs.

5. Luxurious Downtown Owosso Loft

Luxurious Downtown Owosso Loft
Owosso
9.8 out of 10, Exceptional, (60 reviews)
"Wonderful place to stay. "
United States
Richard
The price is HK$1,169
HK$2,275 total
includes taxes & fees
6 Oct - 7 Oct
Luxurious Downtown Owosso Loft
A modern kitchen with a central island, stainless steel appliances, and wooden bar stools.

6. Historic Downtown Owosso Loft

Historic Downtown Owosso Loft
Owosso
9.6 out of 10, Exceptional, (42 reviews)
"Enjoyed our stay! Great location, next to food and activities. Loved the look, convenience of everything around us. Thank you for having us. I will book again when we come to see family who lives in corruna."
United States
Christina M.
The price is HK$918
HK$1,711 total
includes taxes & fees
5 Oct - 6 Oct
Historic Downtown Owosso Loft
A brick pathway leading to a building with a red exterior, a sign reading 'BOYER PARK,' and a metal gate with a bicycle symbol.

7. Vintage Main Street Retreat Sleeps 25

Vintage Main Street Retreat Sleeps 25
Ovid
10.0 out of 10, Exceptional, (6 reviews)
"What an great place to stay for an event. We used the kitchen and banquet area for a catered meal of 50 people and the game room up top was a great hang out."
United States
John B.
The price is HK$5,979
HK$10,199 total
includes taxes & fees
5 Oct - 6 Oct
Vintage Main Street Retreat Sleeps 25
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

The Exchange - A Historic Downtown Studio

The Exchange - A Historic Downtown Studio

10/10 Excellent
"Clean. Comfortable. Easy. Affordable."
Cathy M. 1-night trip
Posted 9 hours ago
The Exchange - A Historic Downtown Studio

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Can I find holiday rentals in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middletown has to offer?

Cozy 3 Bedroom in Owosso close to hospital and Curwood Castle.: This holiday home rental outside of Middletown has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What’s there to see and do in Middletown?

While exploring the area, visit family-friendly sights like Steam Railroading Institute, or get outside and enjoy nature at Sleepy Hollow State Park. In the wider area, you’ll find Joseph H. Lebowsky Center and Curwood Castle.

What’s a holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for small groups.