How much does a Middletown vacation package cost?

You can grab a vacation package to this destination from $252 on Expedia. But how much your vacation to Middletown costs will depend on factors like the length of stay, season and hotel choice.

What are the cheapest months to go to Middletown?

You can typically find reduced prices and greater availability in November, December and January. Browse our cheap Middletown vacation packages and you could land some great off-season discounts.

How many days is enough for Middletown?

We'd recommend booking a Middletown vacation for a minimum of 2 days. This will give you time to check off top attractions including Orange County Fair Speedway and Orange County Fairgrounds , and check out neighborhoods like Scotchtown and Mechanicstown. You might even be able to fit in a day trip (or two) beyond Middletown.

Is it worth booking a vacation package to Middletown?

Middletown offers everything you need for a wonderful getaway. Begin your Middletown vacation on a high note by checking out popular attractions like Orange County Fair Speedway .

How to find the best Middletown package deals?

Start your search for a Middletown package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Middletown package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Middletown adventure underway.

Is it cheaper to book a Middletown vacation as a package?

You can enjoy significant savings on your next Middletown retreat by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to see the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.

When to book a vacation package to Middletown?

If you've got your Middletown vacation dates confirmed, book early to snap up some unbeatable deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for quick escapes.

How to plan a trip to Middletown?

Choose when to travel: Check your diary and get packing. Your favorite season and the activities on offer will also help you decide when to escape to Middletown. Budget wisely: In addition to the price of your hotel, you should factor in other expenses too. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Middletown. Use our trip planning tool to explore Middletown: Research every part of your trip to Middletown with this handy planner. Invite family or friends to collaborate on a group trip, search for hotels or things to do and make bookings. Decide how long to go away for: Now that you know more about Middletown, you can figure out the ideal length of your vacation. Create a rough itinerary and give yourself enough time to get through everything on your must-do list. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Middletown vacation package that brings all your bookings together. Book activities and experiences in advance: Whether it's entrance to a big attraction or a day trip in nature, you won't have to worry about missing out on the best Middletown has to offer. Find all the fun things to do in Middletown with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Middletown vacation packages?

Your Middletown trip is meant to be a relaxing escape from your daily routine, not a reason for money worries. So to allow you extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

Middletown Vacation Packages 2026 from $252

Your Middletown Vacation

Our Middletown vacation packages allow you to create your own adventure. Tailor your journey to your needs and interests and make the most of your time in this fabulous city. Orange County Fair Speedway, Galleria at Crystal Run and Orange County Fairgrounds are just a few of the many sights you'll want to see during your trip to Middletown. Your ultimate Middletown vacation is just clicks away. Browse hotels, airfares and more on Expedia for a getaway that's tailored to suit your travel style.

The Latest Middletown vacation packages

Price found within the past 48 hours. Click for updated prices.

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

$252

per person

Feb 20 - Feb 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newburgh (SWF)

8.4/10 Very Good! (1,002 reviews)

Great service. Great price.

Reviewed on Jan 2, 2026

YO1 Longevity & Health Resorts, Catskills

$588

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newburgh (SWF)

8/10 Very Good! (499 reviews)

The premise is amazing but the execution is lacking. The resort is nice. The vibe was quiet and peaceful. There weren't a lot of guests which probably resulted in a minimal amount of staff on site. I stayed in the lakeview suite which game is a bedroom, livingroom area, balcony, a separate attached room with a massage table and a bathroom with a steam shower. The first room I was book in had a working steam in the shower but the actual shower itself didn't work. The second room they booked me in had a working shower and steam but the shower adjustment was broken. The room had some chipping paint on the ceiling also. Outside of that it really is a nice room. The facilities is nice too. A few of the ammenities were not active. The grounds is nice too. Some parts of the resort is definitely Social Media friendly where great contect can be produced. I think you will like it as a quick getaway if you are in the NYC/Albany area but don't go expecting a top tier luxury experience.

Reviewed on Nov 24, 2025

The Kartrite Resort & Indoor Waterpark

$473

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newburgh (SWF)

8.2/10 Very Good! (1,805 reviews)

Everything was great. Staff was on point with everything.

Reviewed on Jan 10, 2026

Sleep Inn & Suites Middletown - Goshen

$291

per person

Feb 20 - Feb 24

found 1 day ago

Roundtrip flight included

Miami (MIA) to Newburgh (SWF)

8.6/10 Excellent! (1,002 reviews)

everything was clean including the restroom. good air conditioning as well as nice mattress with thick pillows. TV was nice I didnt know how to change it to smart TV though as I saw on the Remote it said “Smart”. The shower got hot really quick and it was a nice quiet stay. Breakfast was amazing a lot of options and it tasted good.

Reviewed on Jan 7, 2026

Holiday Inn Express Hotel & Suites Chester by IHG

$363

per person

Mar 6 - Mar 8

found 7 hours ago

Roundtrip flight included

Los Angeles (LAX) to Newburgh (SWF)

8.4/10 Very Good! (1,003 reviews)

Suite I paid for was not available for first night- not sure what went wrong…

Reviewed on Jan 5, 2026

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Middletown Hotel Deals

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY

Fully refundable

$96 nightly

$114 total

Feb 1 - Feb 2

Total with taxes and fees

8.4/10 Very Good! (1,008 reviews)

Check in was easy Nice quiet room Continental breakfast all weekend even though the listing said it was just weekdays. Used the extra blankets in the closet as I like it extra cozy. Loved the in room coffee maker for coffee and tea water. Quick checkout. Economical! Will stay again!

Reviewed on Jan 5, 2026

Hampton Inn by Hilton Middletown

20 Crystal Run Crossing Middletown NY

Fully refundableReserve now, pay when you stay

$81 nightly

$95 total

Jan 27 - Jan 28

Total with taxes and fees

8.4/10 Very Good! (1,008 reviews)

Great staffing, clean rooms!!!

Reviewed on Jan 9, 2026

Courtyard by Marriott Middletown Goshen

24 Crystal Run Xing Middletown NY

Fully refundableReserve now, pay when you stay

$93 nightly

$109 total

Jan 18 - Jan 19

Total with taxes and fees

8.4/10 Very Good! (1,007 reviews)

Room was really nice and spacious and clean. Definitely nicer than most. The lobby was beautiful with fireplaces and comfortable furniture. It was just the food situation and sparse staffing that would make me never stay here again. There was no complimentary coffee in the lobby — even the cheepest ...

Reviewed on Jan 5, 2026

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.

Things to do in and around Middletown

Middletown, New York, is perfect for families and city-themed vacations, offering a variety of activities to enjoy. Visitors can explore resorts, a shopping mall center, and local shopping options. Highlights include vacation tours, day tours, and golf getaways, making it easy to discover the charm of Middletown. Whether you're looking for great vacations or simply to explore the area, Middletown has something for everyone.

Shopping

For shopping, visit Soons Orchards, a public market just 3 miles away, offering local goods and a vibrant atmosphere. Mamakating Farmers Market, located 9 miles away, also provides a great selection. If you're up for a drive, check out the Galleria at Crystal Run for a larger shopping experience.

Recreation

Enjoy a captivating performance at the Paramount Theatre, where culture and romance blend in a family-friendly atmosphere. For outdoor sports enthusiasts, The Rock Sports Complex offers exciting activities, while the Scenic Farms Golf Course provides a serene environment to unwind and play a round of golf amidst beautiful landscapes.

Adventure

Experience thrilling races at Orange County Fair Speedway, where adrenaline meets excitement in the heart of Middletown. For family fun, visit Castle Fun Center, a vibrant arcade and adventure zone located 9 miles away. If you love winter sports, head to Mount Peter Ski Area, 15 miles from Middletown, for skiing adventures.

Nightlife

Middletown offers a vibrant nightlife with venues like the Paramount Theatre for live shows and The Last Lick for tasty drinks. Explore local bars on South Street for a laid-back vibe, and check out dance spots at nearby clubs for a lively evening. Enjoy the friendly atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Middletown

Middletown, New York, is an ideal destination for family vacations, offering a mix of city and entertainment-themed experiences. Visitors can explore urban parks, national state parks, and nearby lakes, perfect for outdoor adventures and family fun. Additionally, there's a local beach to enjoy, making Middletown a well-rounded spot for travelers seeking both relaxation and recreation in a vibrant setting.

Orange County Fairgrounds: Experience the lively atmosphere at the Orange County Fairgrounds, a hub for outdoor family fun. Enjoy various events, from fairs to concerts, showcasing local culture and community spirit in a vibrant setting.
Harness Racing Museum and Hall of Fame: Dive into the rich history of harness racing at this unique museum. Located 6 miles from Middletown, it highlights the sport's culture and significance through engaging exhibits and memorabilia, perfect for sports enthusiasts.
Neversink River: Enjoy the breathtaking scenery along the Neversink River, situated 13 miles from Middletown. Ideal for nature lovers, this tranquil river offers opportunities for fishing, hiking, and picnicking amidst stunning outdoor vistas.

Best time to go to Middletown

The best time to visit Middletown can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Middletown falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Middletown falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	26.8°F (-2.9°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	28.6°F (-1.9°C)	Light Rain	Mostly Cloudy	Average	Average
March	36.1°F (2.3°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	47.5°F (8.6°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	58.5°F (14.7°C)	Light Rain	Mostly Sunny	Average	Average
June	66.6°F (19.2°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	72.7°F (22.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	70.5°F (21.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	63.7°F (17.6°C)	Light Rain	Mostly Sunny	Average	Average
October	52.7°F (11.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	40.6°F (4.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	32.7°F (0.4°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low

Tips to save on your trip to Middletown

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling during the off-peak season (typically March and December to January) for more affordable package holidays to Middletown.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Language	English
Currency	U.S dollars
Closest Airport	Stewart Intl. Airport (SWF)
Population	27,800
Max Temp Winter	35ºF
Max Temp Summer	80ºF
Top Sights	Warwick Valley Winery and Distillery, Castle Fun Center and Paramount Theatre

Language

English

Currency

U.S dollars

Closest Airport

Stewart Intl. Airport (SWF)

Population

27,800

Max Temp Winter

35ºF

Max Temp Summer

80ºF