Highland Mills Holidays from AU$2,974

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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.
Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Price was AU$4,334, price is now AU$2,974 per person
AU$2,974
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
8/10 Very good! (2,471 reviews)
Overall no issues, however the bedding had hair on it and the shower was dirty and disgusting. I wish I brought shower shoes that's how grossed out I was. Seems to be the trend for most NYC hotels which I don't understand at all.

Reviewed on 17 July 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was AU$5,332, price is now AU$3,530 per person
AU$3,530
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
It may have been because of FIFA…in the mornings trying to go down for breakfast was a struggle…the elevators were packed and we had to let several (3-4) go by before finally pushing onto the elevator. The guests were just as polite as the staff…everyone understood.

Reviewed on 17 July 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was AU$5,229, price is now AU$3,469 per person
AU$3,469
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9.6/10 Exceptional! (1,617 reviews)
Amazing stay! The rooftop has magical views of the city. The staff is great, very welcoming and asked us where we were from and if it’s our first time visiting NYC. The room was excellent with great cable tv and clean towels. Comfortable bed and pillows. Completely satisfied with our stay here , definitely will be coming back!

Reviewed on 15 July 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was AU$4,200, price is now AU$3,013 per person
AU$3,013
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
8.8/10 Excellent! (7,519 reviews)
On Broadway, very convenient and good price. Nice room. Comfortable.

Reviewed on 17 July 2026

WestHouse New York

WestHouse New York

5 out of 5
Manhattan
Price was AU$4,609, price is now AU$3,346 per person
AU$3,346
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
8.4/10 Very good! (1,007 reviews)
Staff was super friendly and helpful! Room was clean and well appointed. The daily happy hour is three hours long and includes complimentary beer and wine and lite noshes. Breakfast was fantastic and had something for everyone. GREAT location. Subway is just a few steps away. This is our new favorite property in NYC.

Reviewed on 15 July 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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
The price is AU$207 per night from 2 Aug to 3 Aug
AU$207
2 Aug - 3 Aug
includes taxes & fees
Sleep Inn & Suites Middletown - Goshen
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is AU$192 per night from 10 Aug to 11 Aug
AU$192
10 Aug - 11 Aug
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is AU$157 per night from 30 July to 31 July
AU$157
30 July - 31 July
includes taxes & fees
8.4/10 Very good! (170 reviews)
"The breakfast is minimal, but there are good eating options in the area"

Reviewed on 17 July 2026

Spark by Hilton Fishkill
See all 848 properties in Highland Mills
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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.
See properties

What to do in Highland Mills

LEGOLAND New York Resort Admission Ticket

LEGOLAND New York Resort Admission Ticket

AU$74
per traveller
84% of travellers recommend
LEGOLAND New York Resort Admission Ticket
7 Hour Private Shopping Tour in Woodbury Common Premium Outlets

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

AU$1,128
per traveller
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
See all activities in Highland Mills

Frequently asked questions

How much does a Highland Mills holiday package cost?
You'll find cheap prices from AU$2,974 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?

  1. 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.
  2. 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.
  3. 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.
  4. Bundle your accommodation and airfare: Once you've settled on your trip dates and duration, book the ideal Highland Mills holiday package for you.

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