Highland Mills Holidays from AU$5,212
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Your Highland Mills Holiday
Prepare to experience Highland Mills your way with a custom Highland Mills holiday package! Uncovering the treasures of this interesting city is made simpler with a base in a neighbourhood such as Montrose, which is good for walking, among many other things. If a sightseeing tour is on the to-do list during your trip to Highland Mills, look around well-known attractions like Woodbury Common Premium Outlets, Brotherhood Winery and Palaia Vineyards Winery. Don't put off your visit to this destination any longer. The ultimate Highland Mills holiday is just a few clicks away with Expedia.
The Latest Highland Mills Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Sela V Hotel
AU$6,177
per person
7 Dec - 12 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
9.4/10 Exceptional! (284 reviews)
Great staff, great food, great atmosphere all around. Very cool hotel that has a musicians touch to it. Would definitely book again if I'm in town next time.
Reviewed on 22 Oct 2026
Luxury 1BR located in Prime Yonkers Area
Bryn Mawr
AU$5,596
per person
7 Dec - 12 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to White Plains (HPN)
4.8/10 (6 reviews)
C completely misrepresented did not stay there far from a luxury apartment advised to check into a different location no code or communication prior to check in time at 4 PM. Received emails and poor communication after 6:30 PM apartment smelled very musty and like a dead body was inside, extremely unprofessional and horrible experience.
Reviewed on 5 May 2026
Highland Mills Holiday
Highland Mills Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Westchester County Airport (HPN) |
Population | 4,000 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Bear Mountain State Park, Brotherhood Winery and Mount Peter Ski Area |
Our pick of the best Highland Mills Hotel Deals
Overlook Lodge at Bear Mountain
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
AU$174
3 Nov - 4 Nov
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
AU$155
22 Nov - 23 Nov
includes taxes & fees
Ramada by Wyndham Newburgh/West Point
1289 Route 300 Newburgh NY
Fully refundableReserve now, pay when you stay
AU$108
26 Oct - 27 Oct
includes taxes & fees
4.8/10 (1,001 reviews)
"Was under construction, room was clean and comfortable."
Reviewed on 20 Oct 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
This hippie-inspired winery in a 200-year-old barn pairs distinctive wines and meads with weekend live music. Enjoy vineyard views from the outdoor stage or relax in the rustic tasting room with artisanal pizzas.
What to do in Highland Mills
LEGOLAND New York Resort Admission Ticket
AU$72
per traveller
86% of travellers recommend
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
AU$1,095
per traveller
Frequently asked questions
How much does a Highland Mills holiday package cost?
You'll find cheap prices from AU$5,212 on Expedia for your Highland Mills escape. However, factors like the season, choice of hotel and length of stay will determine how much your holiday to Highland Mills costs.
What are the cheapest months to go to Highland Mills?
January, February and March are the best times to look for cheap Highland Mills holiday packages. Opting to travel in quieter months means you can usually find reduced prices on hotels and flights.
How many days is enough for Highland Mills?
The ideal duration for your Highland Mills holiday depends on what you'd like to do. Usually, a few days to a week will give you enough time to go to all the main sights and discover some hidden spots along the way.
How to find the best Highland Mills package deals?
Start your search for a Highland Mills package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Highland Mills package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Highland Mills adventure off to a flying start.
Is it cheaper to book a Highland Mills holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging stays and flights individually. Better still, you can tailor your Highland Mills trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Highland Mills?
If you have your Highland Mills travel dates locked in, book early to bag some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Highland Mills?
- Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Highland Mills.
- Plan your budget wisely: On top of the price of your stay, you should factor in other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Highland Mills.
- Set the duration of your trip: Start by listing all the activities and sights you want to get to in Highland Mills. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your accommodation and airfare: Once you've settled on your trip dates and duration, book the ideal Highland Mills holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
