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.
The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Jul. 19 - Jul. 22
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
8.8/10 Excellent! (2,398 reviews)
There was no minibar in the room. The breakfast was so basic. The staff was helpful and kind.

Reviewed on May 28, 2024

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Save 100% on your flight
per person
Aug. 21 - Aug. 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.8/10 Excellent! (1,920 reviews)
Stayed for one night. Only needed a hotel to literally shower and sleep. We had a comfortable sleep, but showering was not pleasant. The tub was clogged and filled with water as you’re in the shower. I did not ask to change rooms as we did not have time. Just needed a shower after a day of driving and left for an event. So that was super disappointing given we only needed the room for 2 things. I did tell the front desk at check in so I hope they did something about it for future guests.

Reviewed on May 28, 2024

The William Vale

The William Vale

5 out of 5
Save 100% on your flight
per person
Aug. 2 - Aug. 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,000 reviews)
Amazing hotel love the room and the staff

Reviewed on May 28, 2024

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
per person
Aug. 1 - Aug. 6
found 15 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to New York (JFK)
9.2/10 Wonderful! (540 reviews)
Beautiful hotel with incredible service, spacious rooms, excellent fitness center, and in a great location! I highly recommend this hotel in NYC!

Reviewed on Apr. 22, 2024

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Aug. 21 - Aug. 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.8/10 Excellent! (1,003 reviews)
Great location! Great service!

Reviewed on May 20, 2024

Highland Mills Hotel Deals

La Quinta Inn & Suites by Wyndham Middletown
La Quinta Inn & Suites by Wyndham Middletown
2.5 out of 5
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Jun. 3 to Jun. 4
CA $173
CA $204 total
includes taxes & fees
Jun 3 - Jun 4
9.2/10 Wonderful! (387 reviews)
"The staff was nice. Checking in was very quick and the place is clean."

Reviewed on May 22, 2024

La Quinta Inn & Suites by Wyndham Middletown
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
The price is CA $193 per night from Jun. 3 to Jun. 4
CA $193
CA $216 total
includes taxes & fees
Jun 3 - Jun 4
8.6/10 Excellent! (1,005 reviews)
"Will be returning..nice atmosphere"

Reviewed on May 24, 2024

HYATT house Fishkill/Poughkeepsie
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
The price is CA $173 per night from Jun. 9 to Jun. 10
CA $173
CA $192 total
includes taxes & fees
Jun 9 - Jun 10
8.4/10 Very Good! (1,007 reviews)
"Very nice hotel in all respects"

Reviewed on May 27, 2024

DoubleTree by Hilton Hotel Nanuet
See all 755 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

Frequently asked questions

How much does a Highland Mills vacation package cost?
We make it simple for everyone to travel, with Highland Mills packages starting from as little as CA $824. You’ll have the flexibility to bundle your preferred hotels, airlines and car rental. For the ultimate getaway, why not add a few activities and tours to your travel itinerary?
How do I get a cheap travel package to Highland Mills?
One of the easiest ways to save money (and time) is to combine your bookings with Expedia. Flights, hotels, rental cars and activities — we’ve got everything you need. Pick and choose a combination that best suits you and watch your savings pile up. We know a travel package is never one-size-fits-all. That’s why we offer more than 550 partner airlines and 1,000,000 hotels from all over the world, which lets you customize your Highland Mills vacation.
Where should I stay in Highland Mills?
A vacation in Highland Mills wouldn’t be complete without paying a visit to Woodbury Common Premium Outlets, Palaia Vineyards Winery and Old Glory Mall Shopping Center. Spend your nights near these top attractions and make sightseeing easy.
How far in advance should I book my Highland Mills vacation?
Reserving your spot early with Expedia means one less thing to worry about. A number of air carriers advertise tickets up to 12 months in advance. This is generally the cheapest time to book. If circumstances have left you booking late, discount tickets to Highland Mills sometimes occur just a few weeks before departure.
What does an Expedia Highland Mills travel package include?
Hotels, flights and a shiny set of wheels for all your fun road trip adventures. Simply pick and choose your favorite bundle and get access to great discounts. Once you’ve made your booking, add on a few experiences and tours and watch your savings pile up. When it comes to creating your Highland Mills getaway, the choice is all yours!
What should I know before booking a Highland Mills travel package?
Locking in all the parts of your escape together is an excellent way to save. Bundle your flights, car rentals and hotels into a handy package. But it’s not just hotels. Expedia features all kinds of properties, including vacation rentals such as mountain cabins and spacious residences. You’ve got choices galore!
Can I choose my airline with a Highland Mills Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you sure can! Just select the carrier that suits you and put together your ideal Highland Mills trip.
If I'm not able to travel, can I cancel my Highland Mills vacation package?
Yes, you can cancel your Highland Mills booking if your plans have changed. Whether you’ll incur a penalty or not depends on your hotel, airline or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.

Discover the most popular places to visit in Highland Mills

Image for Palaia Vineyards Winery

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

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

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

CA $1,056
Per adult
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
See all activities in Highland Mills

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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.