Highland Mills Vacations from $533

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Your Highland Mills Vacation

With every last detail organized before you head off, our Highland Mills vacation packages mean you can concentrate on letting the good times roll. Whether you're based in the neighborhood 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 Center. Your ideal Highland Mills vacation is clicks away. Search accommodations, flights and more on Expedia for an adventure that's tailored just for you.

The Latest Highland Mills vacation packages

Price found within the past 48 hours. Click for updated prices.
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Miami (MIA) to New York (JFK)
8.8/10 Excellent! (492 reviews)
My only issue was the bed pillows need updating. They weren’t very comfortable, felt old and were faded.

Reviewed on Jul 22, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (544 reviews)
We stayed here for an overnight for a girls trip with my 8yr old daughter, we had the best time. We will be back!

Reviewed on Jul 30, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
Nice views.. but food at restaurant left a lot to be desired. Also staff presentation was terrible. They need uniforms and a dress code. Booty shorts, wrinkled clothing... its all a part of the experience and everyone looked like they got up out of bed and came to work. Take pride. Its managements fault ..

Reviewed on Jul 30, 2025

Empire Hotel

Empire Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.6/10 Good! (5,769 reviews)
Great location. Pretty interiors. Some of the doors stuck and the ventilation was t great, but they are in the proIn the process of renovations. Pool is only open 11-7.

Reviewed on Aug 2, 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 15 - Sep 21
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Exceedingly above my expectations

Reviewed on Jul 31, 2025

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Discover the most popular places to visit in Highland Mills

Palaia Vineyards Winery

You can enjoy a tasting or tour at Palaia Vineyards Winery during your travels to Woodbury. Discover the mountain views and shops in this family-friendly area.

Palaia Vineyards Winery

Highland Mills Hotel Deals

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd, Suffern, NY
Fully refundable
$104 nightly
The price is $121 total per night from Aug 10 to Aug 11
$121 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (1,006 reviews)
"Beautiful property."

Reviewed on Jul 30, 2025

Crowne Plaza Suffern - Mahwah by IHG
Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

2.5 out of 5
20 Overlook Blvd, Nanuet, NY
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $138 total per night from Aug 31 to Sep 1
$138 total
Aug 31 - Sep 1
Total includes taxes and fees
8.2/10 Very Good! (1,002 reviews)
"Great time."

Reviewed on Aug 1, 2025

Sonesta Simply Suites Nanuet
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $153 total per night from Aug 4 to Aug 5
$153 total
Aug 4 - Aug 5
Total includes taxes and fees
8.2/10 Very Good! (1,001 reviews)
"Great price. Wonderful location. Will be back!"

Reviewed on Jul 31, 2025

Overlook Lodge at Bear Mountain
See all 766 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.

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Frequently asked questions

How much does a Highland Mills vacation package cost?
You'll find cheap prices from $533 on Expedia for your Highland Mills escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Highland Mills costs.
What are the cheapest months to go to Highland Mills?
November, December and January are the best times to search for cheap Highland Mills vacation packages. Opting to travel in less busy months means you'll typically find lower prices on hotels and flights.
How many days is enough for Highland Mills?
Typically, a handful of days is enough to visit the top attractions during your Highland Mills vacation. But if you'd like to have some time to relax or go on day tours, consider extending your trip.
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 vacation as a package?
An Expedia vacation 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 vacation 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. Choose when to travel: Check your diary and get your bags packed. Your favorite season and the type of activities on offer will also help you decide when to escape to Highland Mills.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to airfares and activities. Your hotel will likely be the biggest expense during your trip to Highland Mills.
  3. Use Expedia's trip planning tool to explore Highland Mills: Research every aspect of your trip to Highland Mills with this comprehensive planner. Invite family or friends to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Work out your trip length: Think about how long you want to spend exploring Highland Mills. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  5. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose a Highland Mills vacation package that brings all your bookings together.
  6. Book any activities or excursions: Now to the fun part — locking in everything you want to see and do. Check out some of the exciting things to do in Highland Mills and book your tickets early to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Highland Mills vacation packages?
Your Highland Mills getaway is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to give you a little more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.