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Middletown Vacation Packages

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Middletown Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Jun 12 - Jun 15
just found
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Ice Time Sports Complex and Resorts World Hudson Valley are located nearby.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Stay at this 3-star business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Ice Time Sports Complex and Resorts World Hudson Valley are located nearby.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
per person
Jun 5 - Jun 9
found 17 hours ago
Roundtrip flight included
Dallas (DFW) 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 breakfast and the helpful staff in our reviews. Popular attractions Paramount Theatre and Soons Orchards are located nearby.
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
per person
Jun 17 - Jun 21
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Stay at this 3-star hotel in New Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Hamilton Fish Bridge and National Purple Heart Hall of Honor are located nearby.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

2 out of 5
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
Book a stay at this business-friendly hotel in New Windsor. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hamilton Fish Bridge and Resorts World Hudson Valley are located nearby.
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Chester. 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 Castle Fun Center are located nearby.

Middletown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

2 out of 5
per person
Jul 1 - Jul 5
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
per person
Jun 5 - Jun 9
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
per person
Jun 17 - Jun 21
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)

Middletown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

2 out of 5
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 2 days ago
$164
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $164 found 2 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $169 found 2 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$174 Roundtrip, found 2 days ago
$174
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $174 found 2 days ago
Breeze Airways
Fri, May 9 - Mon, May 12
MCO
Orlando Intl.
SWF
Stewart Intl.
$181 Roundtrip, found 5 hours ago
$181
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Fri, May 9 from Orlando Intl. to Stewart Intl., returning Mon, May 12, priced at $181 found 5 hours ago