Highland Mills Vacations from $350

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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 Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $696, price is now $350 per person
$350
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful

Reviewed on Aug 12, 2025

Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $742, price is now $361 per person
$361
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
8.4/10 Very Good! (9 reviews)
Only one night so did not use the amenities. The refrigerator in the room died in the night so lost my leftovers. The room was clean and the staff was helpful. The shower function was strange. I would stay there again.

Reviewed on Aug 12, 2025

Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
Price was $932, price is now $504 per person
$504
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.6/10 Exceptional! (10 reviews)
Nice stay. Very low bed and little room to get in and out. Great location. If booking through Expedia, be careful to check for shared/private bathroom as the description is misleading.

Reviewed on Aug 22, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,216, price is now $1,202 per person
$1,202
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug 21, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,233, price is now $674 per person
$674
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,296 reviews)
Good hotel for move in of students at UES colleges

Reviewed on Aug 25, 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

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 $122 total per night from Sep 1 to Sep 2
$122 total
Sep 1 - Sep 2
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"Room Space, fridge"

Reviewed on Aug 20, 2025

Sonesta Simply Suites Nanuet
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
$109 nightly
The price is $129 total per night from Sep 2 to Sep 3
$129 total
Sep 2 - Sep 3
Total with taxes and fees
7.2/10 Good! (522 reviews)
"I enjoyed the location. The place was clean and employees were very pleasant"

Reviewed on Aug 21, 2025

The Crossroads Hotel, Newburgh
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
$133 nightly
The price is $151 total per night from Aug 26 to Aug 27
$151 total
Aug 26 - Aug 27
Total with taxes and fees
8.2/10 Very Good! (1,008 reviews)
"The Overlook Lodge is a wonderful property nestled in the woods and yet close to the Inn for dining. Our room was spacious and the beds were very comfortable."

Reviewed on Aug 23, 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 $350 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.