Highland Mills Vacation Packages
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Your Highland Mills Vacation
With every last detail organized before you head off, our Highland Mills vacation packages mean you can concentrate on letting the good times roll. Whether you're based in the neighborhood of Montrose, which is great for walking, or somewhere else, this interesting city offers a world of discoveries. Any trip to Highland Mills needs a well-planned itinerary. Fill yours with famous sights like Woodbury Common Premium Outlets, Brotherhood Winery and Harriman Plaza Shopping Center. Your ideal Highland Mills vacation is clicks away. Search accommodations, flights and more on Expedia for an adventure that's tailored just for you.
Top Highland Mills Vacation Deals
Price found within the past 48 hours. Click for updated prices.
33 Hotel, New York City, Seaport
Manhattan
CA $1,466
per person
Sep 21 - Sep 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,006 reviews)
When checking in the front desk informed me that I had $42 to spend in room order including patronage at the restaurant on site. They did not mention that the spend doesn’t include or cannot apply to gratuity. I spent $40 on the entire bill at the restaurant and the hotel only took off the portion without the gratuity. The toilet was not flushing well and toward the end of my stay the water never stopped running so I had to call the front desk at 10pm. The elevator was not working but the technician appeared to not communicate to hotel guests by just standing there. I had to carry 3 bags and took a few steps down to another elevator.
Reviewed on Aug 11, 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
CA $1,671
per person
Nov 3 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (3,841 reviews)
El lugar es perfecto pero el papel de baño y otras cositas no son buenas deberían agregar un microondas
Reviewed on Aug 11, 2026
Ready to book your vacation to Highland Mills?
Highland Mills Hotel Deals
Crowne Plaza Suffern - Mahwah by IHG
3 Executive Blvd Suffern NY
Fully refundable
CA $170
CA $198 total
Aug 23 - Aug 24
includes taxes & fees
9/10 Wonderful! (1,033 reviews)
"Great, clean and comfortable bed. No carpets anywhere which is a plus. Beautiful interior and lobby to hang out by"
Reviewed on Aug 10, 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
CA $153
CA $178 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (1,037 reviews)
"Very clean property, bit further out from most of the other hotels but it is newer. Getting into the property is a bit more complicated as you enter via the storage center’s driveway"
Reviewed on Aug 12, 2026
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Fully refundable
CA $148
CA $175 total
Sep 10 - Sep 11
includes taxes & fees
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.
Stay near popular Highland Mills attractions
Palaia Vineyards Winery
You can enjoy a tasting or tour at Palaia Vineyards Winery during your travels to Woodbury. Discover the mountain views and shops in this family-friendly area.
What to do in Highland Mills
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
CA $1,095
per traveller
Frequently asked questions
How much does a Highland Mills vacation package cost?
You'll find cheap prices from CA $1,189 on Expedia for your Highland Mills getaway. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Highland Mills costs.
What are the cheapest months to go to Highland Mills?
If you'd like to snag a cheap Highland Mills vacation package, consider planning a trip in January, February and March. You're likely to find better prices on airfares and hotels during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Highland Mills?
Allow around 4 days for your Highland Mills vacation if you want to immerse yourself in everything that makes this place special. Wander around popular areas, including Woodbury and South Blooming Grove. Then make a beeline for major sights such as Old Glory Mall Shopping Centre and Arrow Park Lake and Lodge. With a clever itinerary, you can keep busy with room for some rest and relaxation too. Want to venture outside of Highland Mills? Consider fitting in a day trip or two.
How to find the best Highland Mills package deals?
Landing a cheap Highland Mills package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, add a couple of filters and see what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable Highland Mills package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Highland Mills vacation as a package?
You can enjoy significant savings on your next Highland Mills escape by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Highland Mills?
If you're planning a spontaneous Highland Mills vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Highland Mills?
- Choose when to get away: Check your schedule and pack your bags. Your favourite time of year and the type of activities available will also help you decide when to escape to Highland Mills.
- Set a budget: Factor in expenses like transportation, flights and meals when calculating how much to put aside for your trip to Highland Mills. Then, select a property that suits your budget, whether that's an affordable option or a more upscale getaway.
- Work out your trip length: Consider how much time you want to spend discovering Highland Mills. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
- Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, book the ideal Highland Mills vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
