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.
New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Manhattan
Price was CA $2,558, price is now CA $1,421 per person
CA $1,421
per person
Jul 1 - Jul 5
found 12 hours ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (4,371 reviews)
The staff were amazing the minute we arrived and the room was spacious and clean. I will always stay here when visiting NY.

Reviewed on Apr 27, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $5,336, price is now CA $3,027 per person
CA $3,027
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,001 reviews)
Don’t ever think you will check in prior to the late 4pm check in. No matter what. Not even 5 minutes.

Reviewed on Apr 17, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was CA $2,934, price is now CA $1,703 per person
CA $1,703
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,000 reviews)
Excellent great service good food

Reviewed on Apr 23, 2026

The William Vale

The William Vale

5 out of 5
Price was CA $2,611, price is now CA $1,542 per person
CA $1,542
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,042 reviews)
View from the Gotham Queen was amazing!

Reviewed on Apr 27, 2026

The Pierre, A Taj Hotel, New York

The Pierre, A Taj Hotel, New York

5 out of 5
Manhattan
Price was CA $6,643, price is now CA $4,046 per person
CA $4,046
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (1,007 reviews)
Great stay. Wonderful people. Needs some updating but recommend

Reviewed on Apr 23, 2026

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Highland Mills Hotel Deals

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
The price is CA $167 per night from May 4 to May 5
CA $167
CA $197 total
May 4 - May 5
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
Rooms have definitely been smoked in. First room we had someone must have just smoked in there. Ash in the window/ very accommodating with switching our room. It wasn’t bad but it wasn’t great

Reviewed on Apr 27, 2026

Sleep Inn & Suites Middletown - Goshen
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 $155 per night from May 10 to May 11
CA $155
CA $181 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (1,107 reviews)
Large room at the very rear of the building overlooking the parking lot.

Reviewed on Apr 25, 2026

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
The price is CA $157 per night from Apr 29 to Apr 30
CA $157
CA $193 total
Apr 29 - Apr 30
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
Awesome experience!

Reviewed on Apr 26, 2026

Overlook Lodge at Bear Mountain
See all 854 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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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

CA $129
per adult
Bear Mountain State Park+ BeaconTown 1-Day Tour From NY
7 Hour Private Shopping Tour in Woodbury Common Premium Outlets

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

CA $1,075
per traveller
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
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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.