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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 Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
Price was $280, price is now $246 per person
$246
per person
Feb 5 - Feb 8
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Book a stay at this business-friendly motel in Montgomery. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions City Winery Hudson Valley and Orange County Farmers Museum are located nearby.
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 18 hours 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 18 hours 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.
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 18 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 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 18 hours 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 18 hours 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.
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 18 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.
Cottage Suites

Cottage Suites

2 out of 5
Price was $364, price is now $315 per person
$315
per person
Jan 21 - Jan 25
found 1 day 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.

Chester 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 18 hours 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 18 hours ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
Price was $617, price is now $517 per person
$517
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newburgh (SWF)
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 18 hours ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)

Chester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
Price was $554, price is now $471 per person
$471
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newburgh (SWF)
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
Save 100% on your flight
Price was $3,963, price is now $3,300 per person
$3,300
per person
Dec 22 - Dec 27
found 3 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newburgh (SWF)
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
Price was $591, price is now $502 per person
$502
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newburgh (SWF)
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was $578, price is now $526 per person
$526
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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 4 days ago
$137
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Dec 4 from Orlando Intl. to Stewart Intl., returning Sun, Dec 7, priced at $137 found 4 days ago
Breeze Airways
Thu, Dec 4 - Sun, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$142 Roundtrip, found 6 days ago
$142
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Dec 4 from Orlando Intl. to Stewart Intl., returning Sun, Dec 7, priced at $142 found 6 days ago
Breeze Airways
Thu, Dec 4 - Sun, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$143 Roundtrip, found 4 days ago
$143
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Dec 4 from Orlando Intl. to Stewart Intl., returning Sun, Dec 7, priced at $143 found 4 days ago
Breeze Airways
Thu, Dec 4 - Sun, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$147 Roundtrip, found 6 days ago
$147
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Dec 4 from Orlando Intl. to Stewart Intl., returning Sun, Dec 7, priced at $147 found 6 days ago