Highland Mills Holidays from £898

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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.
Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Save 100% on your flight
Price was £1,482, price is now £898 per person
£898
per person
2 Sept - 7 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
8.4/10 Very good! (1,710 reviews)
S/O the staff Angle saved me my car broke down 30 mins before the jayz concert he saved the day good looking man i will Always stay at this hotel and the roof is fire

Reviewed on 13 Jul 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was £3,128, price is now £1,798 per person
£1,798
per person
21 Aug - 26 Aug
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Fabulous experience. Front desk staff was extremely helpful, friendly, and efficient. Especially while checking-in. Would come back again! Rooms are thoughtfully designed and have amazing views!

Reviewed on 5 Jul 2026

The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was £2,942, price is now £1,733 per person
£1,733
per person
23 Sept - 28 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.6/10 Exceptional! (703 reviews)
Great service rooms were amazing

Reviewed on 12 Jul 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 £1,830, price is now £1,113 per person
£1,113
per person
2 Sept - 7 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
Great location

Reviewed on 13 Jul 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Save 100% on your flight
Price was £7,221, price is now £4,424 per person
£4,424
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
9/10 Wonderful! (152 reviews)
Amazing

Reviewed on 29 May 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

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 £108 per night from 2 Aug to 3 Aug
£108
2 Aug - 3 Aug
includes taxes & fees
8.8/10 Excellent! (1,076 reviews)
"The property is very clean and well maintained. The area around the hotel is ok. It is easy to access from the highway. The beds are on the hard side, they aren't the worst I've slept in but they did make my back hurt."

Reviewed on 10 Jul 2026

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 £102 per night from 27 Jul to 28 Jul
£102
27 Jul - 28 Jul
includes taxes & fees
9/10 Wonderful! (1,020 reviews)
"Room is clean, breakfast was good. Excellent for the value"

Reviewed on 12 Jul 2026

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 £77 per night from 12 Aug to 13 Aug
£77
12 Aug - 13 Aug
includes taxes & fees
8.4/10 Very good! (163 reviews)
"Dd"

Reviewed on 10 Jul 2026

Spark by Hilton Fishkill
See all 852 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly 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

£39
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

£588
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 travel package cost?
Browse and book everything in one place with our Highland Mills travel packages, which start from only £898. 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.

Explore a world of travel with Expedia

* 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.