New Windsor Vacation Packages

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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, Storm King Art Center and Ice Time Sports Complex 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.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
per person
Aug 22 - Aug 26
found 24 hours ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
5.4/10 (1,006 reviews)
friendly, clean, ok breakfast, lady taking care of the breakfast area was very helpful and friendly

Reviewed on Jul. 16, 2025

The Kent Collection - The Firefly Inn

The Kent Collection - The Firefly Inn

2 out of 5
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
No reviews
Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
per person
Aug 22 - Aug 26
found 24 hours ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
6.2/10 (1,004 reviews)
Nothing in particular

Reviewed on Jul. 7, 2025

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

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

2 out of 5
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
8.4/10 Very Good! (1,004 reviews)
We'll be back. Best value rooms.

Reviewed on Jul. 13, 2025

Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
per person
Sep 24 - Sep 27
found 8 hours ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
9.6/10 Exceptional! (51 reviews)
Such a dreamy escape. The staff is excellent, friendly, and always ready to help. The rooms are serene and comfortable. Amazing spa and spa staff. Restaurant is also top-notch

Reviewed on May 15, 2025

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New Windsor Hotel Deals

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

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

2 out of 5
915 Union Ave, New Windsor, NY
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Jul 20 to Jul 21
CA $147
CA $166 total
Jul 20 - Jul 21
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
"We'll be back. Best value rooms."

Reviewed on Jul. 13, 2025

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

Homewood Suites Stewart Airport

3 out of 5
180 Breunig Rd, New Windsor, NY
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Jul 27 to Jul 28
CA $233
CA $263 total
Jul 27 - Jul 28
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Clean, convenient and breakfast was good."

Reviewed on Jul. 14, 2025

Homewood Suites Stewart Airport
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Aug 3 to Aug 4
CA $150
CA $177 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (751 reviews)
"The only thing that could be better is the toilet paper hanger."

Reviewed on Jul. 16, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen
See all 1,003 properties in New Windsor
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

What to do in New Windsor

Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

CA $181
per adult
Beacon: Gourmet Beacon Food Tour
Taste the Hudson Valley with Gourmet Beacon Food Tour

Taste the Hudson Valley with Gourmet Beacon Food Tour

CA $184
per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
7 Hour Private Shopping Tour in Woodbury Common Premium Outlets

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

CA $1,065
per traveller
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
See all activities in New Windsor

Frequently asked questions

How much does a New Windsor vacation package cost?
You'll find cheap prices from CA $583 on Expedia for your New Windsor escape. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to New Windsor costs.
What are the cheapest months to go to New Windsor?
You can generally find lower rates and greater availability in January, February and March. Explore our cheap New Windsor vacation packages and you could get some great off-season deals.
How many days is enough for New Windsor?
To get the most out of your New Windsor vacation, we recommend staying for 2 days. Divide your time between discovering Algonquin Park, Orange County Choppers and other well-known attractions, on top of exploring neighbourhoods like Orange Lake and Vails Gate. If you've got some time to spare, add a day trip or tour to your New Windsor vacation itinerary.
Is it worth booking a vacation package to New Windsor?
New Windsor offers everything you need for an unforgettable escape. Begin your New Windsor vacation on a high note by checking out major attractions like National Purple Heart Hall of Honour.
How to find the best New Windsor package deals?
Finding a cheap New Windsor package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most pocket-friendly New Windsor package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a New Windsor vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking hotels and flights individually. Better still, you can personalize your New Windsor trip to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to New Windsor?
Secure incredible bargains by booking your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu New Windsor escape.
How to plan a trip to New Windsor?

  1. Choose when to travel: Check your schedule and get packing. Your favourite season and the available activities will also help you decide when to escape to New Windsor.
  2. Set a budget: Consider costs such as food, flights and transportation when working out how much to save for your trip to New Windsor. Then, choose a hotel that fits your budget, whether that's an affordable option or a more upscale getaway.
  3. Decide how long to go away for: Now that you're up to speed on New Windsor, you can work out the perfect length of your vacation. Pull together a rough itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored New Windsor vacation package.

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