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.
Ready to book your vacation to Highland Mills?
Highland Mills Hotel Deals
Overlook Lodge at Bear Mountain
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
CA $160
CA $198 total
Sep 27 - Sep 28
includes taxes & fees
8.4/10 Very good! (1,001 reviews)
"The property is a bit dated and its a bit odd to have to drive to the Inn to check in but it was mostly OK. Very rustic at the lodge and no staff onsite"
Reviewed on Sep 24, 2026
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Fully refundable
CA $163
CA $193 total
Oct 20 - Oct 21
includes taxes & fees
Crowne Plaza Suffern - Mahwah by IHG
3 Executive Blvd Suffern NY
Fully refundable
CA $166
CA $193 total
Sep 28 - Sep 29
includes taxes & fees
9/10 Wonderful! (1,041 reviews)
"All great"
Reviewed on Sep 23, 2026
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
Sunset Sips Cruise — DJ, Open Bar & Hudson River Views
CA $52
per adult
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
CA $1,080
per traveller
Frequently asked questions
How much does a Highland Mills vacation package cost?
You'll find cheap prices from CA $1,444 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.
