Middletown Vacations 2026 from CA $746

Middletown flight + hotel packages

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

Sleep Inn & Suites Monroe - Woodbury

CA $746

per person

May 16 - May 20

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Newburgh (SWF)

Book a stay at this business-friendly hotel in Monroe. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodbury Common Premium Outlets and Museum Village are located nearby.

Top Middletown hotels deals

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY

Free cancellation

CA $139

CA $164 total

Apr 21 - Apr 22

includes taxes & fees

Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Orange County Community College and Paramount Theatre are located nearby.

Pool

Breakfast included

Courtyard by Marriott Middletown Goshen

24 Crystal Run Xing Middletown NY

CA $128

CA $151 total

Apr 19 - Apr 20

includes taxes & fees

Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions LEGOLAND® New York and Galleria at Crystal Run are located nearby.

Pool

Pet-friendly

La Quinta Inn & Suites by Wyndham Middletown-Goshen

551 Route 211 E Middletown NY

Free cancellation

Reserve now, pay when you stay

CA $152

CA $180 total

Apr 19 - Apr 20

includes taxes & fees

Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.

Pool

Breakfast included

Tru by Hilton Middletown

41 Dunning Road Middletown NY

Free cancellation

Reserve now, pay when you stay

CA $123

CA $145 total

Apr 21 - Apr 22

includes taxes & fees

Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions LEGOLAND® New York and Orange County Fairgrounds are located nearby.

Breakfast included

Pet-friendly

Hampton Inn by Hilton Middletown

20 Crystal Run Crossing Middletown NY

Free cancellation

Reserve now, pay when you stay

CA $127

CA $150 total

Apr 21 - Apr 22

includes taxes & fees

Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LEGOLAND® New York and Galleria at Crystal Run are located nearby.

Pool

Breakfast included

Holiday Inn Express & Suites Middletown - Goshen by IHG

20 MED PARC ROAD Middletown NY

CA $150

CA $178 total

Apr 26 - Apr 27

includes taxes & fees

Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LEGOLAND® New York and Galleria at Crystal Run are located nearby.

Pool

Breakfast included

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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.

Popular places to visit

Orange County Fairgrounds

Enjoy an outing to Orange County Fairgrounds during your stay in Mechanicstown. Discover the area's festivals and churches.

Overview of Cold Spring and Hudson Highlands State Park in Fall, New York - October 2024

Highland Lakes State Park

You can take time to visit Highland Lakes State Park during your travels to Middletown. While in this family-friendly area, you can savor the top-notch restaurants.

Lake George on a summer day, in Bolton, New York

Highland Lake

Commune with nature and explore the great outdoors at Highland Lake during your travels in Middletown. While in this family-friendly area, you can savor the top-notch restaurants.

Middletown Vacations

Got your tickets booked and paid for and your suitcase ready to go? Read on for a few basic Middletown tips before you go.

From the center of Newburgh, you'll need to travel west for 20 miles (32 kilometers) to get to this neighborhood.

Ready to meet the locals? 29,000 people live in Newburgh.

Places to visit in Middletown

What is it that makes stuffing yourself with snacks just prior to getting on a dizzying carnival ride seem like a good idea? Try not to lose your lunch at Orange County Fairgrounds! And there's more. The intimacy and mastery of live theater is difficult to ignore. Secure tickets to a play at Paramount Theatre and experience its magic and charm for yourself!

Where do you fly into for Middletown?

Board the plane and catch forty winks. Once you've arrived at Liberty International Airport (EWR), you'll need to travel about 55 miles (89 kilometers) to reach the center of Middletown.

Frequently asked questions

How much are vacation packages to Middletown?

Vacation packages, which include hotels and flights in Middletown, are priced from as little as CA $746. Turn your travel dreams into reality and lock in your trip with Travelocity today.

How long should my Middletown vacation be?

Around 2 nights is what many visitors book for their Middletown vacation. That's a great guide, but there's plenty more to explore if you allow yourself a few extra days.

Where can I get the best vacation package deals for Middletown?

It's difficult to beat Travelocity when it comes to piecing together your Middletown package deal. There are at least 400 airlines and 1,000,000 properties around the world to select from. Plan your escape now and get ready to cross another exciting destination off your must-visit list.

Why should I book my Middletown vacation package with Travelocity?

Savings, support and a stress-free booking are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you have access to round-the-clock support. With the Travelocity Price Match Guarantee, you know you'll always get the best deal available.

Will I save money on my Middletown car rental if I book it with a hotel or flight?

With a Middletown vacation package, you can bundle your flight, car and hotel bookings and save loads. If you're in the mood to uncover the best of this fantastic destination, why not make a beeline for Times Square? This top sight is 88 kilometers from Middletown. With a rental car, you'll be there in no time.

Which airport is best for Middletown?

Liberty Intl. Airport (EWR) is 88 kilometers from the downtown area and is the starting point for many unforgettable experiences. Alternatively, LaGuardia Airport (LGA) is 88 kilometers away from central Middletown and Stewart Intl. Airport (SWF) is 29 kilometers away from central Middletown.

What is there to do in Middletown?

While veering off the tourist trail is no doubt rewarding, you shouldn't ignore the popular sights that make a place famous. Orange County Fair Speedway and Orange County Fairgrounds are just two of them in Middletown.

Where should I stay when visiting Middletown?

If you're looking for someplace comfortable to lay your head, take a look at the Holiday Inn Express & Suites Middletown - Goshen, an IHG Hotel. It's the top pick for many travelers.