
Deals on vacations and trips to Middletown
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Middletown flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.

Sleep Inn & Suites Middletown - Goshen
Price was $270, price is now $226 per person
$226
per person
Jan 10 - Jan 12
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Newburgh (SWF)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport
Price was $316, price is now $228 per person
$228
per person
Jan 8 - Jan 13
found 23 hours ago
Roundtrip flight included
Miami (MIA) to Newburgh (SWF)
This motel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. A safe deposit box is provided and the front desk is staffed around-the-clock.

YO1 Longevity & Health Resorts, Catskills
Save 100% on your flight
Price was $889, price is now $644 per person
$644
per person
Jan 16 - Jan 19
found 20 hours ago
Roundtrip flight included
San Juan (SJU) to Newburgh (SWF)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the indoor pool and perks like free self parking.

Homewood Suites Stewart Airport
Price was $423, price is now $351 per person
$351
per person
Jan 23 - Jan 26
found 6 hours ago
Roundtrip flight included
Fort Myers (RSW) to Newburgh (SWF)
This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like buffet breakfast and free self parking. Free WiFi in public areas, a lobby fireplace, and express check-out are also on offer.

Hampton Inn & Suites Newburgh Stewart Airport
Price was $395, price is now $330 per person
$330
per person
Jan 23 - Jan 26
found 6 hours ago
Roundtrip flight included
Fort Myers (RSW) to Newburgh (SWF)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free airport shuttle. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Top Middletown hotels deals

Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Free Cancellation
$93 nightly
The price is $109 total per night
$109 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included

La Quinta Inn & Suites by Wyndham Middletown-Goshen
551 Route 211 E Middletown NY
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $122 total per night
$122 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included

Hampton Inn by Hilton Middletown
20 Crystal Run Crossing Middletown NY
Free Cancellation
Reserve now, pay when you stay
$78 nightly
The price is $92 total per night
$92 total
Dec 23 - Dec 24
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included

Courtyard by Marriott Middletown Goshen
24 Crystal Run Xing Middletown NY
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $109 total per night
$109 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A 24-hour business center, express check-out, and luggage storage are also on offer.
Pool
Pet friendly

Tru by Hilton Middletown
41 Dunning Road Middletown NY
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $106 total per night
$106 total
Dec 14 - Dec 15
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free English breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and free newspapers.
Breakfast included
Pet friendly

Super 8 by Wyndham Middletown
563 Route 211 E Middletown NY
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $83 total per night
$83 total
Dec 7 - Dec 8
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Luggage storage and a safe deposit box are also provided.
Parking included
Free WiFi
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
Galleria at Crystal Run
4/5(20 reviews)
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.
Orange County Fair Speedway
4/5(5 reviews)
Catch an event at Orange County Fair Speedway during your trip to Mechanicstown. Discover the area's festivals and churches.
Orange County Fairgrounds
4.5/5(4 reviews)
Enjoy an outing to Orange County Fairgrounds during your stay in Mechanicstown. Discover the area's festivals and churches.
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