Title: New Windsor Vacation Packages & Trips 2026 from CA $593 | Expedia.ca

[Hotels in New Windsor](https://expedia.ca/New-Windsor-Hotels.d10021.Travel-Guide-Hotels)[Vacation Rentals in New Windsor](https://expedia.ca/New-Windsor-Vacation-Rentals.d10021.Travel-Guide-VacationRentals)[Things to do in New Windsor](https://expedia.ca/Things-To-Do-In-New-Windsor.d10021.Travel-Guide-Activities)[New Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-New-Windsor.d10021.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6148010/b4469cf7-6c52-4383-a18b-1573522aca84.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# New Windsor Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

Photo by Wanderlustfemale

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#### Your New Windsor Vacation

There's no better way to travel than with one of our vacation packages to New Windsor. The rich history and spectacular views are two of the convincing reasons to spend some time in this captivating city. [Dia Beacon](https://www.expedia.ca/Dia-Beacon-Beacon.d6093761.Vacation-Attraction), [Storm King Art Center](https://www.expedia.ca/Storm-King-Art-Center-Cornwall.d6148010.Vacation-Attraction) and [Ice Time Sports Complex](https://www.expedia.ca/Ice-Time-Sports-Complex-Newburgh.d6181843.Vacation-Attraction) are just some of the attractions you'll want to explore during your trip to New Windsor. A couple of quick clicks is all it takes to put together a tailored New Windsor vacation on Expedia.

## Top New Windsor Vacation Deals

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

![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sleep Inn & Suites Middletown - Goshen

CA $593

per person

Feb 13 - Feb 18

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Newburgh (SWF)

8.6/10 Excellent! (1,002 reviews)

everything was clean including the restroom. good air conditioning as well as nice mattress with thick pillows. TV was nice I didnt know how to change it to smart TV though as I saw on the Remote it said “Smart”. The shower got hot really quick and it was a nice quiet stay. Breakfast was amazing a lot of options and it tasted good.

Reviewed on Jan 7, 2026

![Courtyard by Marriott Newburgh Stewart Airport](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Courtyard by Marriott Newburgh Stewart Airport

CA $643

per person

Feb 13 - Feb 18

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Newburgh (SWF)

8.2/10 Very Good! (691 reviews)

Great location and it felt pretty safe overall. The only downside was that the room didn’t have proper humidity ventilation, and the hallway AC made it cold, so we had to use the heater to balance the temperature. Other than that, the staff was super friendly, and the property was very well maintained.

Reviewed on Oct 30, 2025

![The Crossroads Hotel, Newburgh](https://images.trvl-media.com/lodging/1000000/20000/14500/14410/5440914b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Crossroads Hotel, Newburgh

CA $633

per person

Feb 13 - Feb 18

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Newburgh (SWF)

7.2/10 Good! (679 reviews)

Beds comfy. Clean and quiet.

Reviewed on Dec 31, 2025

![Newburgh Inn](https://images.trvl-media.com/lodging/1000000/10000/1700/1692/39bbd1ec_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Newburgh Inn

CA $665

per person

Feb 13 - Feb 18

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Newburgh (SWF)

5.4/10 (111 reviews)

I have wondering things to say about my enjoying everything regards my choice to book & stay at The Red Roof Roof Hotel & Suites in Newburgh, NY. The staff is outstanding. They all are professional & friendly. It’s a safe, clean hotel. The bonuses at this particular hotel include gorgeous sunrises & sunsets. Overlooking a lake that faces east. I highly recommend choosing The Red Roof when in this area. Sincerely, Jeannine C

Reviewed on Nov 10, 2025

![Holiday Inn Express & Suites Middletown - Goshen by IHG](https://images.trvl-media.com/lodging/42000000/41530000/41524600/41524586/697f516f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Holiday Inn Express & Suites Middletown - Goshen by IHG

CA $732

per person

Feb 13 - Feb 18

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Newburgh (SWF)

8.8/10 Excellent! (695 reviews)

Stayed on Sunday night, 12/28\. It’s a nice , modern and clean hotel. I had some mess up when booking the room with Expedia but the front desk lady resolved our issue very quickly . She was very responsive and helpful. Breakfast was very good, lots of options, the area was spotless and constantly being cleaned. There is great coffee machine in the lobby with coffee and tea station that added pleasure to our stay. The pool was nice and clean and so is gym. Would definitely come back and recommend to others.

Reviewed on Dec 29, 2025

## Ready to book your vacation to New Windsor?

Choose your dates

## New Windsor Hotel Deals

![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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

915 Union Ave New Windsor NY

Fully refundableReserve now, pay when you stay

8.2/10 Very Good! (1,017 reviews)

Our stay was wonderful, and its always our go-to hotel when we are in the area and need a place to stay. The only comment was that the tub was super slippery without some type of bathmat in the bottom, as we almost had serious falls because of it. But that was the only thing, everything else was ...

Reviewed on Jan 9, 2026

[Get rates](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=875625&PinnedHotelID=875625&HadPinnedHotel=true&regionId=10021)

[](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=875625&PinnedHotelID=875625&HadPinnedHotel=true&regionId=10021)

![Homewood Suites Stewart Airport](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/771d3275_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Homewood Suites Stewart Airport

180 Breunig Rd New Windsor NY

Fully refundableReserve now, pay when you stay

CA $170

CA $192 total

Jan 25 - Jan 26

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

The room was well appointed and clean. The bed was very comfortable. People need to move away from the doors when they go outside to smoke as it makes entering the building quite stinky

Reviewed on Dec 27, 2025

[](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=1764709&PinnedHotelID=1764709&HadPinnedHotel=true&regionId=10021)

![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hampton Inn Harriman Woodbury

60 Centre Dr Central Valley NY

Fully refundableReserve now, pay when you stay

CA $136

CA $167 total

Jan 25 - Jan 26

includes taxes & fees

9.2/10 Wonderful! (1,029 reviews)

Breakfast was fresh rooms were clean. Staff were very friendly and parking seemed very safe.

Reviewed on Jan 6, 2026

[](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=1789296&PinnedHotelID=1789296&HadPinnedHotel=true&regionId=10021)

[See all 1,039 properties in New Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F01%2F2026&endDate=13%2F01%2F2026&regionId=10021)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### What to do in New Windsor

![Bear Mountain State Park+ BeaconTown 1-Day Tour From NY](https://mediaim.expedia.com/localexpert/50302489/1ceb0837-f410-471c-80a4-908b6cbc0dd2.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Bear Mountain State Park+ BeaconTown 1-Day Tour From NY

CA $122

per adult

[](https://expedia.ca/things-to-do/bear-mountain-state-park-beacontown-1-day-tour-from-ny.a50302489.activity-details)

![7 Hour Private Shopping Tour in Woodbury Common Premium Outlets](https://mediaim.expedia.com/localexpert/46892132/cdde0413-4011-4c4f-84f3-dd3c0fe6c3c3.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax

CA $1,066

per traveller

[](https://expedia.ca/things-to-do/black-suv-7hs-staying-woodbury-outlets-up-to-6pax-free-tax.a46892132.activity-details)

[See all activities in New Windsor](https://expedia.ca/things-to-do/search?rid=10021)

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- [Peekskill Vacations ](https://www.expedia.ca/Peekskill.d183704.Destination-Travel-Guides)
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- [Stormville Airport Antique Show & Flea Market ](https://www.expedia.ca/Stormville-Airport-Antique-Show-Flea-Market-Stormville.d553248621532664682.Vacation-Attraction)
- [Tuxedo Park Vacations ](https://www.expedia.ca/Tuxedo-Park.d6171670.Destination-Travel-Guides)
- [West Point Vacations ](https://www.expedia.ca/West-Point.d9700.Destination-Travel-Guides)
- [Woodbury Common Premium Outlets ](https://www.expedia.ca/Woodbury-Common-Premium-Outlets-Central-Valley.d6127054.Vacation-Attraction)

- [Car rental Beacon ](https://www.expedia.ca/Car-Rentals-In-Beacon.d6173904.Car-Rental-Guide)
- [Car rentals near Dia Beacon ](https://www.expedia.ca/Car-Rentals-In-Dia-Beacon.d6093761.Car-Rental-Guide)
- [Car rental Newburgh ](https://www.expedia.ca/Car-Rentals-In-Newburgh.d6023343.Car-Rental-Guide)
- [National Car Rental Rental Cars in Newburgh ](https://www.expedia.ca/National-Car-Rental-Car-Rentals-In-Newburgh.d6023343-c42.Car-Rental-Guide-Suppliers)
- [Rent A Wreck Rental Cars in Newburgh ](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Newburgh.d6023343-c33.Car-Rental-Guide-Suppliers)
- [Sixt Rental Cars in Beacon ](https://www.expedia.ca/Sixt-Car-Rentals-In-Beacon.d6173904-c35.Car-Rental-Guide-Suppliers)

- [Beacon Vacation Rentals ](https://www.expedia.ca/Beacon-Vacation-Rentals.d6173904.Travel-Guide-VacationRentals)
- [Cornwall-On-Hudson Vacation Rentals ](https://www.expedia.ca/Cornwall-On-Hudson-Vacation-Rentals.d6338911.Travel-Guide-VacationRentals)
- [Newburgh Vacation Rentals ](https://www.expedia.ca/Newburgh-Vacation-Rentals.d6023343.Travel-Guide-VacationRentals)

- [Things to do in Beacon ](https://www.expedia.ca/Things-To-Do-In-Beacon.d6173904.Travel-Guide-Activities)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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