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Middletown Vacation Rentals & One Degree Stays Homes

About Middletown Vacation Rentals

There are more than 66 vacation rentals that are available in Middletown. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Middletown.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Middletown, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Middletown. Places to stay near Middletown are 576.16 ft² on average, with prices averaging US $261 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Middletown with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Middletown

Type Count
Vacation Homes 20
Holiday Apartments 16
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Middletown

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Middletown.

Weather in Middletown, NY

View the weather forecast for Middletown before booking your Middletown Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Middletown, NY

OneDegreeStays offers a large selection of top attractions around Middletown. Research things to do on your vacation before you visit Middletown.


Paramount Theatre
Orange County Fairgrounds
Galleria at Crystal Run
Orange County Fair Speedway
Orange Regional Medical Center
Woodbury Common Premium Outlets
Mountain Creek Ski Resort
Bear Mountain State Park
United States Military Academy
Crystal Springs Golf Resort
Resorts World Catskills
Delaware Water Gap National Recreation Area
Mountain Creek Waterpark
Monticello Casino and Raceway
State University of New York-New Paltz
Dia Beacon
Storm King Art Center

Other Places to Stay in Middletown, NY


Howells 92 Properties
Orange County Fair Speedway 76 Properties
Mechanicstown 75 Properties
Paramount Theatre 75 Properties
Orange County Fairgrounds 72 Properties
Scotchtown 63 Properties
Orange Regional Medical Center 62 Properties
Washington Heights 61 Properties
Galleria at Crystal Run 61 Properties
Wallkill 59 Properties

Frequently Asked Questions About Middletown?

What are the top vacation rentals in Middletown?

There are a lot of options in Middletown. If you plan on staying in the Middletown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Middletown:

Which vacation homes in Middletown are best for families?

If you are looking for a family-friendly vacation home in Middletown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Middletown:

How many onedegreestays vacation rentals are available in Middletown?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 66 in the Middletown area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Middletown. 


People Also Ask

There are 66 Middletown, NY Vacation Rentals

Recently Booked Vacation Rentals in Middletown