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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.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
Price was $360, price is now $275 per person
$275
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Stay at this 3-star business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ice Time Sports Complex and Resorts World Hudson Valley are located nearby.
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
Price was $346, price is now $281 per person
$281
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
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.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was $435, price is now $356 per person
$356
per person
Dec 18 - Dec 21
found 21 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

2.5 out of 5
Price was $340, price is now $286 per person
$286
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 LEGOLAND® New York and Galleria at Crystal Run are located nearby.
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
Price was $420, price is now $356 per person
$356
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
Price was $413, price is now $351 per person
$351
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Stay at this 3-star 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.
Cottage Suites

Cottage Suites

2 out of 5
Price was $501, price is now $429 per person
$429
per person
Jan 21 - Jan 27
found 10 hours ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Stay at this hotel in Middletown. Enjoy free WiFi. Popular attractions Paramount Theatre and Orange County Fair Speedway are located nearby.
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
Price was $358, price is now $308 per person
$308
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.

Middletown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
Price was $360, price is now $275 per person
$275
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
Price was $346, price is now $281 per person
$281
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
Price was $492, price is now $401 per person
$401
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was $435, price is now $356 per person
$356
per person
Dec 18 - Dec 21
found 21 hours ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)

Middletown Vacation Packages 5-7 Night Stays

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

Cottage Suites

2 out of 5
Price was $501, price is now $429 per person
$429
per person
Jan 21 - Jan 27
found 10 hours ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was $1,203, price is now $1,064 per person
$1,064
per person
Dec 22 - Dec 29
found 15 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Newburgh (SWF)
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
Price was $1,581, price is now $1,398 per person
$1,398
per person
Dec 22 - Dec 29
found 15 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Newburgh (SWF)
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
Price was $1,001, price is now $911 per person
$911
per person
Dec 22 - Dec 29
found 15 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Newburgh (SWF)

Top Flight Deals

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

Breeze Airways
Thu, Dec 4 - Sun, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Dec 4 from Orlando Intl. to Stewart Intl., returning Sun, Dec 7, priced at $137 found 5 days ago
Breeze Airways
Thu, Dec 4 - Sun, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$143 Roundtrip, found 5 days ago
$143
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Dec 4 from Orlando Intl. to Stewart Intl., returning Sun, Dec 7, priced at $143 found 5 days ago
Breeze Airways
Thu, Dec 4 - Sun, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$148 Roundtrip, found 5 days ago
$148
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Dec 4 from Orlando Intl. to Stewart Intl., returning Sun, Dec 7, priced at $148 found 5 days ago
Breeze Airways
Fri, Dec 5 - Sun, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$162 Roundtrip, found 4 days ago
$162
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Dec 5 from Orlando Intl. to Stewart Intl., returning Sun, Dec 7, priced at $162 found 4 days ago