Book Exclusive Middletown Vacation Packages

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Middletown flight + hotel packages

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Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
per person
Dec. 26 - Dec. 28
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and a nightclub. Popular attractions Hamilton Fish Bridge and Resorts World Hudson Valley are located nearby.
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
per person
Dec. 27 - Jan. 2
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Newburgh (SWF)
Stay at this 5-star luxury resort in Gardiner. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tuthilltown Spirits and DM Weil Gallery are located nearby.
Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
per person
Dec. 30 - Jan. 2
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Newburgh (SWF)
Stay at this motel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.
La Quinta Inn & Suites by Wyndham Middletown

La Quinta Inn & Suites by Wyndham Middletown

2.5 out of 5
per person
Jan. 2 - Jan. 5
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Newburgh (SWF)
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.
Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
per person
Dec. 30 - Jan. 2
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Newburgh (SWF)
Book a stay at this business-friendly motel in Montgomery. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions City Winery Hudson Valley and Orange County Farmers Museum are located nearby.

Top Middletown hotels deals

La Quinta Inn & Suites by Wyndham Middletown

La Quinta Inn & Suites by Wyndham Middletown

2.5 out of 5
551 Route 211 E, Middletown, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $129 per night
CA $129
CA $153 total
includes taxes & fees
19 Dec - 20 Dec
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
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

2.5 out of 5
20 Crystal Run Crossing, Middletown, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $118 per night
CA $118
CA $139 total
includes taxes & fees
13 Dec - 14 Dec
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
Tru by Hilton Middletown

Tru by Hilton Middletown

2.5 out of 5
41 Dunning Road, Middletown, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $141 per night
CA $141
CA $167 total
includes taxes & fees
3 Dec - 4 Dec
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
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6, Middletown, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $127 per night
CA $127
CA $144 total
includes taxes & fees
9 Dec - 10 Dec
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 Paramount Theatre and Soons Orchards are located nearby.
Pool
Breakfast included
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
24 Crystal Run Xing, Middletown, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $123 per night
CA $123
CA $146 total
includes taxes & fees
17 Dec - 18 Dec
Stay at this 3-star 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
Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
563 Route 211 E, I-84 Exit 4W Rt 17 Exit 120, Middletown, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $104 per night
CA $104
CA $123 total
includes taxes & fees
27 Nov - 28 Nov
Stay at this motel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.
Breakfast included
Parking 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 Fair Speedway

Catch an event at Orange County Fair Speedway during your trip to Mechanicstown. Discover the area's festivals and churches.

Orange County Fair Speedway

Galleria at Crystal Run

During your visit to Middletown, you can search for that perfect souvenir at Galleria at Crystal Run. While in this family-friendly area, you can savor the top-notch restaurants.

Galleria at Crystal Run

Orange County Fairgrounds

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

Orange County Fairgrounds

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 $500. 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.

Photos of local treasures

Browse Middletown vacation photos for more inspiration

Photo by Vincent Ramundo
Photo by Vincent Ramundo