Highland Mills Vacation Packages

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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.

Top Highland Mills Vacation Deals

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

3 out of 5
Save 100% on your flight
per person
Sep 19 - Sep 26
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (2,096 reviews)
Staff was friendly. Room was clean.

Reviewed on Jul. 12, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
per person
Aug 28 - Sep 4
found 8 hours ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.4/10 Very Good! (532 reviews)
Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery..

Reviewed on Jul. 10, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
per person
Aug 28 - Sep 4
found 8 hours ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (480 reviews)
This hotel is a pure gem. The service is fantastic, the front desk team works to make sure you are truly taken care of, including our dog. Very calm vibe, its super clean, quiet and perfect. Already looking at another couple of nights in August!

Reviewed on Jul. 11, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 16
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
What a great place! The location was fantastic, the staff was great, and the views were unbelievable. Definitely want to come back some day!

Reviewed on Jul. 12, 2025

Night Hotel Broadway

Night Hotel Broadway

2.5 out of 5
Manhattan
Save 100% on your flight
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
7/10 Good! (2,169 reviews)
Bed was on the softer side but comfy. Room was spacious. Bathroom was clean and all of the most forgotten items were stocked in the bathroom. Staff was friendly.

Reviewed on Jul. 14, 2025

Ready to book your vacation to Highland Mills?

 

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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 refundableReserve now, pay when you stay
The price is CA $113 per night from Aug 3 to Aug 4
CA $113
CA $131 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (1,011 reviews)
"Second time staying. No complaints at all."

Reviewed on Jul. 13, 2025

Crowne Plaza Suffern - Mahwah by IHG
La Quinta Inn & Suites by Wyndham Middletown-Goshen
La Quinta Inn & Suites by Wyndham Middletown-Goshen
3 out of 5
551 Route 211 E, Middletown, NY
The price is CA $150 per night from Aug 3 to Aug 4
CA $150
CA $177 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (747 reviews)
Comfortable, clean and convenient
"The manager, as well as the other customer service per person at the front desk or both amazingly professional and helpful"

Reviewed on Jul. 13, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen
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
The price is CA $194 per night from Aug 12 to Aug 13
CA $194
CA $220 total
Aug 12 - Aug 13
includes taxes & fees
8.2/10 Very Good! (1,011 reviews)
"Area around the lodge was covered with trash and overflowing trash cans."

Reviewed on Jul. 11, 2025

Overlook Lodge at Bear Mountain
See all 775 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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

CA $181
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

CA $184
per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
7 Hour Private Shopping Tour in Woodbury Common Premium Outlets

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

CA $1,065
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 vacation package cost?
You'll find cheap prices from CA $698 on Expedia for your Highland Mills getaway. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Highland Mills costs.
What are the cheapest months to go to Highland Mills?
If you'd like to snag a cheap Highland Mills vacation package, consider planning a trip in January, February and March. You're likely to find better prices on airfares and hotels during these quieter months --- perfect for travellers wishing to save money.
How many days is enough for Highland Mills?
Allow around 4 days for your Highland Mills vacation if you want to immerse yourself in everything that makes this place special. Wander around popular areas, including Woodbury and South Blooming Grove. Then make a beeline for major sights such as Old Glory Mall Shopping Centre and Arrow Park Lake and Lodge. With a clever itinerary, you can keep busy with room for some rest and relaxation too. Want to venture outside of Highland Mills? Consider fitting in a day trip or two.
How to find the best Highland Mills package deals?
Landing a cheap Highland Mills package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, add a couple of filters and see what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable Highland Mills package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Highland Mills vacation as a package?
You can enjoy significant savings on your next Highland Mills escape by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Highland Mills?
If you're planning a spontaneous Highland Mills vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Highland Mills?

  1. Choose when to get away: Check your schedule and pack your bags. Your favourite time of year and the type of activities available will also help you decide when to escape to Highland Mills.
  2. Set a budget: Factor in expenses like transportation, flights and meals when calculating how much to put aside for your trip to Highland Mills. Then, select a property that suits your budget, whether that's an affordable option or a more upscale getaway.
  3. Work out your trip length: Consider how much time you want to spend discovering Highland Mills. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, book the ideal Highland Mills vacation package for you.

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