Title: New Windsor Vacation Packages & Trips 2026 from CA $416 | 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

- ##  
Plan, book, travel with confidence
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Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
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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.

![Howard Johnson by Wyndham Newburgh/West Point](https://images.trvl-media.com/lodging/1000000/10000/7700/7652/8a35f36a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Howard Johnson by Wyndham Newburgh/West Point

CA $416

per person

Feb 14 - Feb 16

found 21 hours ago

Roundtrip flight included

Toronto (YTO) to Newburgh (SWF)

6/10 (1,002 reviews)

The room was good and served it's purpose.

Reviewed on Jan 9, 2026

![Super 8 by Wyndham Montgomery Maybrook](https://images.trvl-media.com/lodging/1000000/860000/855600/855538/7ac7ec53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Super 8 by Wyndham Montgomery Maybrook

CA $515

per person

Feb 26 - Mar 2

found 3 hours ago

Roundtrip flight included

Toronto (YYZ) to Newburgh (SWF)

6.4/10 (1,000 reviews)

Breakfast was not all good

Reviewed on Dec 16, 2025

![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

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

CA $566

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip flight included

Ottawa (YOW) to Newburgh (SWF)

8.4/10 Very Good! (1,002 reviews)

Great service. Great price.

Reviewed on Jan 2, 2026

![Caldwell House Bed & Breakfast](https://images.trvl-media.com/lodging/6000000/5120000/5112000/5111988/fdae1673_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Caldwell House Bed & Breakfast

CA $965

per person

Feb 13 - Feb 16

found 17 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Newburgh (SWF)

9/10 Wonderful! (474 reviews)

Great place to stay. Wonderful breakfasts. Gracious and warm hospitality.

Reviewed on May 28, 2024

![Tru by Hilton Middletown](https://images.trvl-media.com/lodging/37000000/36250000/36247800/36247736/935c6486_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Tru by Hilton Middletown

CA $424

per person

Feb 13 - Feb 15

found 22 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Newburgh (SWF)

8.6/10 Excellent! (947 reviews)

Yes, room was clean.THe staff

Reviewed on Jan 6, 2026

## 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=26%2F01%2F2026&endDate=27%2F01%2F2026&selected=875625&PinnedHotelID=875625&HadPinnedHotel=true&regionId=10021)

[](https://expedia.ca/Hotel-Search?startDate=26%2F01%2F2026&endDate=27%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 $169

CA $191 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=13%2F01%2F2026&endDate=14%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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- [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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