Highland Mills Vacations from $222

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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.
Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $463, price is now $222 per person
$222
per person
Jan 26 - Jan 29
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
15.6/10 Exceptional! (80 reviews)
I wish there was a coffee maker in the room, also the TV was very small and angled away from the bed. It was super quiet, which was great, and very clean and warm.

Reviewed on Nov 16, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $1,005, price is now $434 per person
$434
per person
Feb 15 - Feb 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
18.4/10 Exceptional! (2,008 reviews)
Staff and amenities were fabulous!! Stayed here for 5 nights on a trip for tourism and it was perfectly situated for the Broadway shows and to get away from the hustle and bustle of being a tourist.

Reviewed on Nov 24, 2025

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was $646, price is now $315 per person
$315
per person
Feb 12 - Feb 15
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
17.2/10 Exceptional! (2,613 reviews)
The location was ideal for our stay. The restaurant food was amazing.

Reviewed on Nov 22, 2025

Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY

3 out of 5
Price was $458, price is now $229 per person
$229
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
16.8/10 Exceptional! (1,001 reviews)
Beautiful place to be

Reviewed on Nov 20, 2025

Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was $547, price is now $277 per person
$277
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
16.8/10 Exceptional! (1,508 reviews)
The Staff (doorman) was very nice. I was headed to Pier 88 so it was very close and just one block away. I had an excellent stay!

Reviewed on Nov 24, 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

What to do in Highland Mills

Bear Mountain State Park+ BeaconTown 1-Day Tour From NY

Bear Mountain State Park+ BeaconTown 1-Day Tour From NY

$94
per adult
Bear Mountain State Park+ BeaconTown 1-Day Tour From NY
See all activities in Highland Mills

Highland Mills Hotel Deals

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
$105 nightly
The price is $123 total per night from Dec 4 to Dec 5
$123 total
Dec 4 - Dec 5
Total with taxes and fees
8.2/10 Very Good! (1,024 reviews)
I enjoyed my stay, the staff were very professional and pleasant. The rooms were very clean and neat. I felt safe.

Reviewed on Nov 23, 2025

Sonesta Simply Suites Nanuet
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4 out of 5
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $123 total per night from Dec 7 to Dec 8
$123 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
Location was convent to hop on and off traveling towards the city. Hotel staff were pleasantly upbeat during the entire stay

Reviewed on Nov 17, 2025

DoubleTree by Hilton Hotel Nanuet
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
$101 nightly
The price is $115 total per night from Dec 1 to Dec 2
$115 total
Dec 1 - Dec 2
Total with taxes and fees
8.2/10 Very Good! (1,009 reviews)
Great experience highly recommend.

Reviewed on Nov 14, 2025

Overlook Lodge at Bear Mountain
See all 784 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.

Find the Best Highland Mills Vacation Packages

Highland Mills Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Westchester County Airport (HPN)
Population
4,000
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Brotherhood Winery, Mount Peter Ski Area and Castle Fun Center

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Frequently asked questions

How much does a Highland Mills vacation package cost?
You'll find cheap prices from $222 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.

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