Search Deals on
Chester Vacation Packages

Build your package with 2 more options

Leaving from

Going to

Departing

Returning

Travelers

Room 1

Adults

ChildrenAges 2 to 17

InfantsYounger than 2

Add specific hotel dates

Chester
New York
United States of America
North America
Hotwire.com

Chester Flight + Hotel Packages

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

The Crossroads Hotel, Newburgh

3 out of 5

Price was $308, price is now $243 per person

$243

per person

Jan 30 - Feb 2

found 7 hours ago

Roundtrip flight included

Austin (AUS) to Newburgh (SWF)

Book a stay at this 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.

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5

Save 100% on your flight

Price was $427, price is now $310 per person

$310

per person

Feb 4 - Feb 9

found 1 day ago

Roundtrip flight included

Charlotte (CLT) 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.

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5

Save 100% on your flight

Price was $624, price is now $502 per person

$502

per person

Feb 18 - Feb 24

found 11 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 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

3 out of 5

Price was $306, price is now $262 per person

$262

per person

Jan 30 - Feb 2

found 7 hours ago

Roundtrip flight included

Austin (AUS) to Newburgh (SWF)

Stay at this 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.

Candlewood Suites Middletown Goshen by IHG

2.5 out of 5

Price was $450, price is now $387 per person

$387

per person

Feb 20 - Feb 23

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Newburgh (SWF)

Stay at this hotel in Middletown. Popular attractions LEGOLAND® New York and Galleria at Crystal Run are located nearby.

Super 8 by Wyndham Middletown

2.5 out of 5

Price was $420, price is now $378 per person

$378

per person

Feb 4 - Feb 9

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Newburgh (SWF)

Stay at this motel in Middletown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.

Wildflower Farms, Auberge Collection

5 out of 5

Save 100% on your flight

Price was $2,150, price is now $1,971 per person

$1,971

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Newburgh (SWF)

Book a stay at this luxury resort in Gardiner. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tuthilltown Spirits and DM Weil Gallery are located nearby.

Residence Inn by Marriott Middletown Goshen

3 out of 5

Price was $446, price is now $414 per person

$414

per person

Feb 20 - Feb 23

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 in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.