Search Deals on
New Windsor Vacation Packages

Build your package with 2 more options
Photo by Wanderlustfemale

New Windsor Flight + Hotel Packages

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 $342, price is now $294 per person
$294
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
Price was $428, price is now $340 per person
$340
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Stay at this 4-star family-friendly hotel in Monticello. Enjoy 5 restaurants, 2 bars/lounges, and water park access (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Resorts World Catskills and Concord Monster Golf Course 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 $639, price is now $516 per person
$516
per person
Dec 14 - Dec 20
found 12 hours ago
Roundtrip flight included
Nashville (BNA) 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.
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was $406, price is now $339 per person
$339
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
Price was $463, price is now $392 per person
$392
per person
Nov 7 - Nov 9
found 8 hours ago
Roundtrip flight included
Charlotte (CLT) 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.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was $1,124, price is now $964 per person
$964
per person
Nov 23 - Nov 30
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 breakfast and the helpful staff in our reviews. Popular attractions Paramount Theatre and Soons Orchards are located nearby.
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
Price was $1,297, price is now $1,126 per person
$1,126
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Stay at this 4.5-star luxury hotel in Monticello. Enjoy a full-service spa, 6 restaurants, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Resorts World Catskills and Concord Monster Golf Course are located nearby.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
Price was $383, price is now $335 per person
$335
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.

New Windsor 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 $342, price is now $294 per person
$294
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was $406, price is now $339 per person
$339
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
Price was $534, price is now $447 per person
$447
per person
Nov 7 - Nov 10
found 8 hours ago
Roundtrip flight included
Charlotte (CLT) to Newburgh (SWF)
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was $439, price is now $377 per person
$377
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)

New Windsor Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
Price was $639, price is now $516 per person
$516
per person
Dec 14 - Dec 20
found 12 hours ago
Roundtrip flight included
Nashville (BNA) to Newburgh (SWF)
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was $1,124, price is now $964 per person
$964
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
Price was $1,297, price is now $1,126 per person
$1,126
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
Price was $869, price is now $772 per person
$772
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)

Top Flight Deals

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

JetBlue Airways
Wed, Oct 22 - Mon, Oct 27
MCO
Orlando Intl.
HPN
Westchester County
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Oct 22 from Orlando Intl. to Westchester County, returning Mon, Oct 27, priced at $149 found 1 day ago
JetBlue Airways
Tue, Oct 28 - Sat, Nov 1
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Oct 28 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Sat, Nov 1, priced at $157 found 1 day ago
JetBlue Airways
Mon, Oct 27 - Fri, Oct 31
PBI
Palm Beach Intl.
HPN
Westchester County
$167 Roundtrip, found 3 days ago
$167
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Oct 27 from Palm Beach Intl. to Westchester County, returning Fri, Oct 31, priced at $167 found 3 days ago
Breeze Airways
Thu, Dec 4 - Sun, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$173 Roundtrip, found 11 hours ago
$173
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Thu, Dec 4 from Orlando Intl. to Stewart Intl., returning Sun, Dec 7, priced at $173 found 11 hours ago