Highland Mills Vacations from $351

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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.
Somerset Hills Hotel, Tapestry Collection by Hilton

Somerset Hills Hotel, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $602, price is now $351 per person
$351
per person
Nov 15 - Nov 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.8/10 Excellent! (215 reviews)
Overall great location and friendly staff

Reviewed on Oct 6, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,710, price is now $1,511 per person
$1,511
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Every staff person I interacted with was friendly and helpful. Loved the views and location. Wished there was more room to walk in the living room when the pull out sofa was open.

Reviewed on Sep 28, 2025

ModernHaus SoHo

ModernHaus SoHo

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,914, price is now $1,086 per person
$1,086
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.6/10 Excellent! (1,004 reviews)
Spacious rooms, friendly staff, clean, lots of shopping and dinning options.

Reviewed on Sep 15, 2025

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,144, price is now $654 per person
$654
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (4,712 reviews)
Ducha en malas condiciones.

Reviewed on Oct 9, 2025

Ace Hotel New York

Ace Hotel New York

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,798, price is now $1,052 per person
$1,052
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8/10 Very Good! (1,007 reviews)
Great place to stay, good vibes

Reviewed on Oct 2, 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

Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

$133
per adult
Beacon: Gourmet Beacon Food Tour
Taste the Hudson Valley with Gourmet Beacon Food Tour

Taste the Hudson Valley with Gourmet Beacon Food Tour

$135
per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
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
$112 nightly
The price is $130 total per night from Oct 19 to Oct 20
$130 total
Oct 19 - Oct 20
Total with taxes and fees
8.2/10 Very Good! (1,012 reviews)
"Room was very clean, love the fact that it has a kitchenette in the room. Bed was very comfortable."

Reviewed on Oct 9, 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
$125 nightly
The price is $142 total per night from Nov 3 to Nov 4
$142 total
Nov 3 - Nov 4
Total with taxes and fees
8.2/10 Very Good! (1,004 reviews)
"Incredibly peaceful when walking in the forest. Swimming in the lake and stream was amazing"

Reviewed on Oct 6, 2025

Overlook Lodge at Bear Mountain
Holiday Inn Express Ramsey-Mahwah by IHG

Holiday Inn Express Ramsey-Mahwah by IHG

2.5 out of 5
946 Route 17 North, Ramsey, NJ
Fully refundable
$126 nightly
The price is $144 total per night from Oct 12 to Oct 13
$144 total
Oct 12 - Oct 13
Total with taxes and fees
9/10 Wonderful! (1,005 reviews)
"Everything was clean and super practical, which is what I need for business travel. 24-hour coffee and tea is a nice touch. The only tiny suggestion I’d make is a lotion dispenser in the shower area. It was located by the sink (outside the bathroom), and if you’re traveling with someone who doesn’t ..."

Reviewed on Oct 6, 2025

Holiday Inn Express Ramsey-Mahwah by IHG
See all 768 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.

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 $351 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.

Explore a world of travel with Expedia

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.