Highland Mills Holidays
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- Plan, book, travel with confidence
- Better togetherSave up to Rp16.000.000 when you book a flight and hotel together*
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Top hotels in Highland Mills
Crowne Plaza Suffern - Mahwah by IHG
3 Executive Blvd Suffern NY
Fully refundable
Rp2.183.434
Rp2.540.970 total
23 Aug - 24 Aug
includes taxes & fees
9/10 Wonderful! (1,033 reviews)
"Great, clean and comfortable bed. No carpets anywhere which is a plus. Beautiful interior and lobby to hang out by"
Reviewed on 10 Aug 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
Rp1.879.185
Rp2.182.203 total
20 Aug - 21 Aug
includes taxes & fees
9/10 Wonderful! (1,035 reviews)
"Great stay"
Reviewed on 10 Aug 2026
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Fully refundable
Rp1.962.406
Rp2.318.093 total
8 Sept - 9 Sept
includes taxes & fees
8.8/10 Excellent! (1,124 reviews)
"The hotel was clean, and the bed was very comfortable, making for a pleasant stay. The staff were friendly, welcoming, and very helpful throughout our visit. However, I was disappointed that there were no non-pork meat options available at breakfast. Having more breakfast choices would have made ..."
Reviewed on 10 Aug 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
Sunset Sips Cruise — DJ, Open Bar & Hudson River Views
Rp677.392
per adult
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
Rp14.090.700
per traveller
Frequently asked questions
How much does a Highland Mills holiday package cost?
You'll find cheap prices 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.
