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New Windsor Vacation Packages

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New Windsor Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

2.5 out of 5
Price was $443, price is now $428 per person
$428
per person
May 18 - May 21
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Monroe. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodbury Common Premium Outlets and Museum Village are located nearby.
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was $611, price is now $497 per person
$497
per person
Jun 3 - Jun 6
found 23 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG

2.5 out of 5
Price was $1,030, price is now $985 per person
$985
per person
May 31 - Jun 6
found 6 hours ago
Roundtrip flight included
Greenville (GSP) 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.
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
Price was $582, price is now $564 per person
$564
per person
Jun 3 - Jun 6
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Stay at this 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.
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
Price was $844, price is now $837 per person
$837
per person
Jun 1 - Jun 6
found 7 hours ago
Roundtrip flight included
Greenville (GSP) 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.
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

2.5 out of 5
Price was $724, price is now $719 per person
$719
per person
Jun 1 - Jun 6
found 7 hours ago
Roundtrip flight included
Greenville (GSP) 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 & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

2.5 out of 5
Price was $818, price is now $814 per person
$814
per person
May 31 - Jun 6
found 6 hours ago
Roundtrip flight included
Greenville (GSP) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Montgomery. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions City Winery Hudson Valley and Orange County Farmers Museum 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 $830, price is now $825 per person
$825
per person
May 31 - Jun 6
found 6 hours ago
Roundtrip flight included
Greenville (GSP) 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.

New Windsor 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
Price was $395, price is now $395 per person
$395
per person
May 18 - May 21
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was $611, price is now $497 per person
$497
per person
Jun 3 - Jun 6
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

2.5 out of 5
Price was $443, price is now $428 per person
$428
per person
May 18 - May 21
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
Price was $582, price is now $564 per person
$564
per person
Jun 3 - Jun 6
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)

New Windsor Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

2.5 out of 5
Price was $710, price is now $701 per person
$701
per person
Jun 1 - Jun 6
found 7 hours ago
Roundtrip flight included
Greenville (GSP) to Newburgh (SWF)
Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG

2.5 out of 5
Price was $1,030, price is now $985 per person
$985
per person
May 31 - Jun 6
found 6 hours ago
Roundtrip flight included
Greenville (GSP) to Newburgh (SWF)
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
Price was $844, price is now $837 per person
$837
per person
Jun 1 - Jun 6
found 7 hours ago
Roundtrip flight included
Greenville (GSP) to Newburgh (SWF)
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

2.5 out of 5
Price was $724, price is now $719 per person
$719
per person
Jun 1 - Jun 6
found 7 hours ago
Roundtrip flight included
Greenville (GSP) to Newburgh (SWF)

Top Flight Deals

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

Breeze Airways
Sat, Jun 6 - Sat, Jun 6
MCO
Orlando Intl.
HPN
Westchester County
$162 Roundtrip, found 1 hour ago
$162
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Jun 6 from Orlando Intl. to Westchester County, returning Sat, Jun 6, priced at $162 found 1 hour ago
Breeze Airways
Thu, May 14 - Mon, May 18
MCO
Orlando Intl.
SWF
Stewart Intl.
$168 Roundtrip, found 6 days ago
$168
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, May 14 from Orlando Intl. to Stewart Intl., returning Mon, May 18, priced at $168 found 6 days ago
American Airlines
Wed, Apr 15 - Mon, Apr 20
TPA
Tampa Intl.
HPN
Westchester County
$197 Roundtrip, just found
$197
Roundtrip
just found
Select American Airlines flight, departing Wed, Apr 15 from Tampa Intl. to Westchester County, returning Mon, Apr 20, priced at $197 just found
JetBlue Airways
Sat, Jul 11 - Wed, Jul 22
PBI
Palm Beach Intl.
HPN
Westchester County
$207 Roundtrip, found 1 hour ago
$207
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Sat, Jul 11 from Palm Beach Intl. to Westchester County, returning Wed, Jul 22, priced at $207 found 1 hour ago