Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Start by selecting your hotel
Start by selecting your hotel
Start by selecting your hotel

Save up to $603 by booking Flight + Hotel.

Search 590,000 properties and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more


Middletown Vacation Packages

Middletown is part of Newburgh, a city with 29,000 permanent inhabitants.

Save Time and Money with a Middletown Package Deal

Expedia will help you save with a flight and hotel deal. We're here to help savvy tourists locate their preferred package deals. With the extra money, now you'll be able to experience a little more in Middletown.

By securing one of our package deals, you save up to $583.

Around 400 partner airlines and 321,000 hotels worldwide are ready for you to book via our substantial global database.

Now's the time to plan your vacation, with some of the best prices and deals at Expedia.

You don't have to worry about postponing your travel plans, as we do not charge additional cancellation fees for almost all of our hotel bookings.

Middletown Vacation Packages

It sits 18 miles to the west of Stewart International Airport, and 20 miles from the city's center.

If you plan to see some of this region's most popular sites, then you've picked an ideal location. Don't miss the Harness Racing Museum & Hall of Fame and the Harness Racing Museum and Hall of Fame. Be sure that you don't neglect the Orange County Genealogical Society and Galleria at Crystal Run. Howells and New Hampton are close by neighborhoods that you might like to head down to.

Accommodation in Middletown

Don't expect to find a huge range of hotel deals in Middletown, so it would be wise to explore the listings and deals on Expedia's lodging page.

The Courtyard by Marriott Middletown and Hampton Inn by Hilton Middletown are the best lodgings in Middletown.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.


Top Hotel Deals

See all 129 Properties in Middletown
Microtel Inn & Suites by Wyndham Middletown $92
Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown

19 Crystal Run Crossing, Middletown
     
    3.9
    of 5, from 684 reviews
    2.0 out of 5.0

    Located in the heart of Middletown, this hotel is 1.6 mi (2.5 km) from Galleria at Crystal Run and 2.7 mi (4.4 km) from Orange County Fair Speedway. Orange County Fairgrounds and Paramount Theatre are also within 6 mi (10 km).

    Super 8 by Wyndham Middletown $73
    Super 8 by Wyndham Middletown

    Super 8 by Wyndham Middletown

    563 Route 211 E, Middletown
       
      3.0
      of 5, from 625 reviews
      2.0 out of 5.0

      Situated in Middletown, this motel is within 3 mi (5 km) of Orange County Fairgrounds, Orange County Fair Speedway, and Paramount Theatre. Soons Orchards and Goshen Historic Track are also within 9 mi (15 km).

      Sleep Inn & Suites Middletown - Goshen $91
      Sleep Inn & Suites Middletown - Goshen

      Sleep Inn & Suites Middletown - Goshen

      3491 Route 6, Middletown
         
        4.6
        of 5, from 158 reviews
        2.5 out of 5.0

        Located in the heart of Middletown, this hotel is 1.9 mi (3.1 km) from Paramount Theatre and 1.9 mi (3.1 km) from Soons Orchards. Orange County Fair Speedway and Orange County Fairgrounds are also within 6 mi (10 km).

        Courtyard by Marriott Middletown $121
        Courtyard by Marriott Middletown

        Courtyard by Marriott Middletown

        24 Crystal Run Xing, Middletown
           
          4.5
          of 5, from 277 reviews
          3.0 out of 5.0

          Situated in Middletown, this hotel is within 3 mi (5 km) of Galleria at Crystal Run, Orange County Fair Speedway, and Orange County Fairgrounds. Paramount Theatre and Soons Orchards are also within 6 mi (10 km).

          Hampton Inn by Hilton Middletown $118
          Hampton Inn by Hilton Middletown

          Hampton Inn by Hilton Middletown

          20 Crystal Run Crossing, Middletown
             
            4.2
            of 5, from 365 reviews
            2.5 out of 5.0

            Situated in the suburbs, this hotel is within 3 mi (5 km) of Galleria at Crystal Run, Orange County Fair Speedway, and Orange County Fairgrounds. Paramount Theatre and Soons Orchards are also within 6 mi (10 km).

            Home2 Suites by Hilton Middletown $134
            Home2 Suites by Hilton Middletown

            Home2 Suites by Hilton Middletown

            600 Route 211 East, Middletown
               
              4.6
              of 5, from 76 reviews
              3.0 out of 5.0

              Situated in Middletown, this hotel is 1.7 mi (2.7 km) from Orange County Fairgrounds and 2.1 mi (3.4 km) from Orange County Fair Speedway. Paramount Theatre and Soons Orchards are also within 9 mi (15 km).

              Wawayanda House on 62 Acres - Multiple Fireplaces!
              Wawayanda House on 62 Acres - Multiple Fireplaces!

              Wawayanda House on 62 Acres - Multiple Fireplaces!

              , Wawayanda
                 
                0.0 out of 5.0

                Situated in Middletown, this vacation home is within 12 mi (20 km) of Soons Orchards, Paramount Theatre, and Witness Monument. Orange County Fair Speedway and Pine Island Town Park are also within 12 mi (20 km).

                Americas Best Value Inn-New Paltz $81
                Americas Best Value Inn-New Paltz

                Americas Best Value Inn-New Paltz

                7 Terwilliger Ln, New Paltz
                   
                  3.8
                  of 5, from 619 reviews
                  2.0 out of 5.0

                  Situated in New Paltz, this motel is within 2 mi (3 km) of State University of New York-New Paltz, G. Steve Jordan Gallery, and Loren Campbell Memorial Field. New Paltz Golf Course and Testimonial Gateway are also within 3 mi (5 km).

                  Top Flight + Hotel Deals

                  Top Deals on Flights

                  These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.