Title: New Windsor Vacation Packages & Trips 2026 from CA $535 | 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/10021/c7e47857-5297-4fca-a2da-20a9979aa9f1.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# New Windsor Vacation Packages

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

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

#### 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.

![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 $535

per person

Apr 3 - Apr 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Newburgh (SWF)

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

Clean room, friendly staff

Reviewed on Feb 11, 2026

![Wildflower Farms, Auberge Collection](https://images.trvl-media.com/lodging/80000000/79880000/79873100/79873064/d940ee3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Wildflower Farms, Auberge Collection

CA $5,612

per person

May 15 - May 19

just found

Roundtrip flight included

Vancouver (YVR) to Newburgh (SWF)

9.4/10 Exceptional! (54 reviews)

Everything was ok, except for the fact that we couldn’t do late check out or that we payed a bit more for a standard room. But everything else was perfect

Reviewed on Dec 13, 2025

![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 $891

per person

May 8 - May 12

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Newburgh (SWF)

8.2/10 Very Good! (691 reviews)

Staff was very nice.

Reviewed on Feb 20, 2026

![Sleep Inn & Suites Monroe - Woodbury](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/0db56af9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sleep Inn & Suites Monroe - Woodbury

CA $615

per person

Apr 3 - Apr 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Newburgh (SWF)

9.4/10 Exceptional! (1,004 reviews)

Very clean , quite and extremely friendly staff Will stay again for next trip

Reviewed on Feb 20, 2026

![Hampton Inn & Suites Newburgh Stewart Airport](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/3df08b3c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hampton Inn & Suites Newburgh Stewart Airport

CA $652

per person

Apr 3 - Apr 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Newburgh (SWF)

9.2/10 Wonderful! (967 reviews)

Room was great.The receptionist was she helped me with everything and she was kind.

Reviewed on Feb 16, 2026

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_10021)

## 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

CA $118

CA $134 total

Mar 1 - Mar 2

includes taxes & fees

8.4/10 Very Good! (1,011 reviews)

Supposed to have a pool with no pool the heating was terrible everything was just bad

Reviewed on Feb 20, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%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 $178

CA $202 total

Mar 15 - Mar 16

includes taxes & fees

9.2/10 Wonderful! (1,001 reviews)

Good

Reviewed on Feb 26, 2026

[](https://expedia.ca/Hotel-Search?startDate=15%2F03%2F2026&endDate=16%2F03%2F2026&selected=1764709&PinnedHotelID=1764709&HadPinnedHotel=true&regionId=10021)

![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Courtyard by Marriott Poughkeepsie

2641 South Road/Route 9 Poughkeepsie NY

Fully refundableReserve now, pay when you stay

CA $144

CA $162 total

Mar 15 - Mar 16

includes taxes & fees

8.8/10 Excellent! (1,000 reviews)

Easy check-in/out. Staff very personable. Clean.

Reviewed on Feb 23, 2026

[](https://expedia.ca/Hotel-Search?startDate=15%2F03%2F2026&endDate=16%2F03%2F2026&selected=5910&PinnedHotelID=5910&HadPinnedHotel=true&regionId=10021)

[See all 1,013 properties in New Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F02%2F2026&endDate=28%2F02%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 $128

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 $1,064

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)

## Explore a world of travel with Expedia

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- [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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