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

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

2 out of 5
per person
Apr 13 - Apr 15
found 24 hours ago
Roundtrip flight included
Portland (PWM) 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.
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Apr 18 - Apr 22
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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.
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
per person
Apr 28 - May 4
found 24 hours ago
Roundtrip non-stop flight included
Bogotá (BOG) 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.
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
per person
Apr 18 - Apr 22
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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.
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
per person
Apr 18 - Apr 22
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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.

Chester Vacation Packages 3-4 Night Stays

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
Apr 18 - Apr 22
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Newburgh (SWF)
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
per person
Apr 18 - Apr 22
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Newburgh (SWF)
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
per person
Apr 18 - Apr 22
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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
Apr 28 - May 4
found 24 hours ago
Roundtrip non-stop flight included
Bogotá (BOG) to Newburgh (SWF)
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
per person
Apr 28 - May 4
found 24 hours ago
Roundtrip non-stop flight included
Bogotá (BOG) to Newburgh (SWF)
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Apr 28 - May 4
found 24 hours ago
Roundtrip non-stop flight included
Bogotá (BOG) 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.
$173 Roundtrip, found 6 days ago
$173
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $173 found 6 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$178 Roundtrip, found 6 days ago
$178
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $178 found 6 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$183 Roundtrip, found 6 days ago
$183
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $183 found 6 days ago
Breeze Airways
Thu, Jul 10 - Mon, Jul 14
TPA
Tampa Intl.
SWF
Stewart Intl.
$751 Roundtrip, found 1 day ago
$751
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jul 10 from Tampa Intl. to Stewart Intl., returning Mon, Jul 14, priced at $751 found 1 day ago