Highland Mills Holidays

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Top hotels in Highland Mills

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
The price is Rp2.107.099 per night from 29 Nov to 30 Nov
Rp2.107.099
Rp2.489.009 total
29 Nov - 30 Nov
includes taxes & fees
8.4/10 Very good! (1,001 reviews)
"We had to wait two hours and a half for our dinner in the large hall. Not even tells us why it took so long."

Reviewed on 12 Nov 2026

Overlook Lodge at Bear Mountain
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 Rp1.696.931 per night from 13 Dec to 14 Dec
Rp1.696.931
Rp1.970.562 total
13 Dec - 14 Dec
includes taxes & fees
9/10 Wonderful! (1,165 reviews)
"Wonderful breakfast! Beautiful, clean room! Will stay here again!!!"

Reviewed on 12 Nov 2026

Hyatt Place Poughkeepsie / Hudson Valley
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd Suffern NY
Fully refundable
The price is Rp2.141.582 per night from 13 Dec to 14 Dec
Rp2.141.582
Rp2.492.266 total
13 Dec - 14 Dec
includes taxes & fees
9/10 Wonderful! (1,052 reviews)
"It was confusing at check-in as I deliberately picked a place that had parking included and upon checking in they charge for parking which is fine but seems like it shouldn’t say free parking and also was a bit thrown to have to put a 50 deposit at a hotel that’s new also as it didn’t seem like they ..."

Reviewed on 10 Nov 2026

Crowne Plaza Suffern - Mahwah by IHG
See all 850 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.

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

Bear Mountain Full-Day Oktoberfest Scenic Cruise

Bear Mountain Full-Day Oktoberfest Scenic Cruise

Rp1.314.213
per adult
84% of travellers recommend
Bear Mountain Full-Day Oktoberfest Scenic Cruise
7 Hour Private Shopping Tour in Woodbury Common Premium Outlets

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

Rp14.013.480
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 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.

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