Highland Mills Holidays from £1,534
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Your Highland Mills Holiday
With every last detail organised before you head off, our Highland Mills holiday packages mean you can concentrate on letting the good times roll. Whether you're based in the neighbourhood 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 Centre. Your ideal Highland Mills holiday is clicks away. Search accommodation, flights and more on Expedia for an adventure that's tailored just for you.
Top Highland Mills Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Loews Regency New York Hotel
Manhattan
£2,283
per person
27 Dec - 3 Jan
found 24 hours ago
Return direct flight included
Edinburgh (EDI) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Great location, staff very friendly, rooms well laid out and extremely clean, food good, tho expensive.
Reviewed on 21 Oct 2026
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 |
Top hotels in Highland Mills
Overlook Lodge at Bear Mountain
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
£92
10 Nov - 11 Nov
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
£82
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
£56
27 Oct - 28 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
£38
per traveller
86% of travellers recommend
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
£582
per traveller
Frequently asked questions
How much does a Highland Mills travel package cost?
Browse and book everything in one place with our Highland Mills travel packages, which start from only £1,534. Choose the hotels and flights that suit your style. Then, add on a few experiences or tours to cap off your unique adventure.
If I'm not able to travel, can I cancel my Highland Mills travel package?
Yes, you can. We get that even the best-laid plans can fail, so we're here to help if you have to make changes to your Highland Mills travel package. You may be able to cancel or change your itinerary at no cost if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, check your itinerary for the nitty-gritty on change fees.
How do I get a cheap travel package to Highland Mills?
Our Highland Mills travel packages mean plenty of savings for the savvy wanderer. For the best deals, simply bundle your flights, hotels and tours into a budget-friendly package. But bargain prices are just the beginning of your next amazing adventure. When you book with Expedia, and you'll have over 550 airlines and 1,000,000 properties across the globe to choose from. No matter your budget or style, there's a travel package with your name on it.
Does Expedia offer Book Now, Pay Later Highland Mills holidays?
Expedia has partnered with online lender Klarna to make your next break easier on your hip pocket. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that suits your budget. Take a look at these flexible payment options:
- Pay monthly holidays: If paying small amounts each month works for you, Klarna offers just that! Paying in easy monthly instalments will make your holiday dreams come true.
- Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Then go for this Book Now, Pay Later option from Klarna.
- Low deposit holidays: Hitting the "book now" button is easier with this payment option. Simply put down a small deposit on your holiday and then start packing your bags.
Where should I stay in Highland Mills?
A getaway to Highland Mills isn't complete without stopping by Woodbury Common Premium Outlets, Gateway Plaza Shopping Centre and Monroe Federal Plaza Shopping Centre. Spend your nights close to these attractions and make sightseeing a breeze.
What are the top hotels in Highland Mills?
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport and Hampton Inn Harriman Woodbury are among the most popular properties in Highland Mills. Why not look up the rates and facilities at each and then make a decision?
How far in advance should I book my Highland Mills holiday?
Search Expedia to compare airfares as soon as you know your travel dates. In most cases, you can purchase a seat up to a year before departure. If you can't find your preferred air carrier, or you're booking late, don't stress. The lowest prices to Highland Mills sometimes occur within weeks of departure.
What does an Expedia Highland Mills travel package include?
Choose from a combination of flights, rental cars and hotels. Once you've made your booking, you can also add on experiences and tours. Want to pick your airfare class? That's easily done too. The choice is all yours when it comes to crafting your perfect Highland Mills getaway.
What should I know before booking a Highland Mills travel package?
You'll pick up excellent savings when you combine your flights, hotels and rental cars into a package. Not just that, booking everything together just makes things easier. So why waste your money or time? Whether you're organising a fancy romantic getaway or a budget solo adventure, explore our travel packages today.
Can I choose my airline with a Highland Mills Expedia travel package?
Yes, definitely. Expedia has over 550 partner airlines to select from worldwide. With so much choice, finding the perfect carrier to whisk you away to Highland Mills will be a snap.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
