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Chester Vacation Packages

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Chester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
per person
Jun 5 - Jun 7
found 24 hours ago
Roundtrip flight included
Houston (IAH) to Newburgh (SWF)
Book a stay at this business-friendly motel in Newburgh. Enjoy free breakfast, free WiFi, and free parking. 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.
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 17 - Jul 20
found 2 hours ago
Roundtrip flight included
Houston (IAH) 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.
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Houston (IAH) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Newburgh. Enjoy free breakfast, free WiFi, and free parking. 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.
Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
Jun 5 - Jun 7
found 24 hours ago
Roundtrip flight included
Houston (IAH) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Newburgh. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Hamilton Fish Bridge and Resorts World Hudson Valley are located nearby.
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
per person
Jun 5 - Jun 7
found 24 hours ago
Roundtrip flight included
Houston (IAH) 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.
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
per person
Jul 18 - Jul 20
found 24 hours 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.
Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
per person
Jul 18 - Jul 20
found 24 hours ago
Roundtrip flight included
Orlando (MCO) 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.

Chester 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 17 - Jul 20
found 2 hours ago
Roundtrip flight included
Houston (IAH) to Newburgh (SWF)
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Houston (IAH) to Newburgh (SWF)

Chester 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 18 - Jun 23
found 18 hours ago
Roundtrip flight included
Houston (IAH) 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, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$154 Roundtrip, found 2 days ago
$154
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $154 found 2 days ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $159 found 2 days ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 2 days ago
$164
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $164 found 2 days ago
Breeze Airways
Thu, May 8 - Sun, May 11
MCO
Orlando Intl.
SWF
Stewart Intl.
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, May 8 from Orlando Intl. to Stewart Intl., returning Sun, May 11, priced at $169 found 2 days ago