Highland Mills Holidays from NZ$4,425

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The Latest Highland Mills Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was NZ$5,502, price is now NZ$4,425 per person
NZ$4,425
per person
25 Sept - 29 Sept
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
9.2/10 Wonderful! (3,652 reviews)
Everything was great.

Reviewed on 12 July 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was NZ$9,665, price is now NZ$6,583 per person
NZ$6,583
per person
25 Sept - 29 Sept
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Fabulous experience. Front desk staff was extremely helpful, friendly, and efficient. Especially while checking-in. Would come back again! Rooms are thoughtfully designed and have amazing views!

Reviewed on 5 July 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was NZ$7,768, price is now NZ$5,790 per person
NZ$5,790
per person
25 Sept - 29 Sept
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Not the standard for a 1 Hotel property. I came in late and the fire alarm was falsely going off the entire time. No courtesy call and no zero attempt to accommodate the guests. The rooms need some work. Felt dingy and could use some serious touch ups and repairs. Just didn’t feel like the others.

Reviewed on 6 July 2026

5th & 55th Residence Club

5th & 55th Residence Club

5 out of 5
Manhattan
Price was NZ$11,222, price is now NZ$8,674 per person
NZ$8,674
per person
25 Sept - 29 Sept
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
8.4/10 Very good! (5 reviews)

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was NZ$5,667, price is now NZ$4,522 per person
NZ$4,522
per person
25 Sept - 29 Sept
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
The best hotel weve stayed in NYC!

Reviewed on 12 July 2026

Highland Mills Holiday

Our pick of the best 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 NZ$241 per night from 4 Aug to 5 Aug
NZ$241
4 Aug - 5 Aug
includes taxes & fees
8.8/10 Excellent! (1,076 reviews)
"The property is very clean and well maintained. The area around the hotel is ok. It is easy to access from the highway. The beds are on the hard side, they aren't the worst I've slept in but they did make my back hurt."

Reviewed on 10 July 2026

Sleep Inn & Suites Middletown - Goshen
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is NZ$238 per night from 10 Aug to 11 Aug
NZ$238
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (1,020 reviews)
"Room is clean, breakfast was good. Excellent for the value"

Reviewed on 12 July 2026

Hyatt Place Poughkeepsie / Hudson Valley
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 NZ$300 per night from 2 Aug to 3 Aug
NZ$300
2 Aug - 3 Aug
includes taxes & fees
8.4/10 Very good! (1,008 reviews)
"Friendly atmosphere and staff. Lots to see and do! A bit outdated so must be ok with a outdoorsy/rustic feel."

Reviewed on 8 July 2026

Overlook Lodge at Bear Mountain
See all 838 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.

Stay near popular Highland Mills attractions

Palaia Vineyards Winery

This hippie-inspired winery in a 200-year-old barn pairs distinctive wines and meads with weekend live music. Enjoy vineyard views from the outdoor stage or relax in the rustic tasting room with artisanal pizzas.
See properties

What to do in Highland Mills

7 Hour Private Shopping Tour in Woodbury Common Premium Outlets

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

NZ$1,374
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 holiday package cost?
You'll find cheap prices from NZ$4,425 on Expedia for your Highland Mills escape. However, factors like the season, choice of hotel and length of stay will determine how much your holiday to Highland Mills costs.
What are the cheapest months to go to Highland Mills?
January, February and March are the best times to look for cheap Highland Mills holiday packages. Opting to travel in quieter months means you can usually find reduced prices on hotels and flights.
How many days is enough for Highland Mills?
The ideal duration for your Highland Mills holiday depends on what you'd like to do. Usually, a few days to a week will give you enough time to go to all the main sights and discover some hidden spots along the way.
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 holiday as a package?
An Expedia holiday 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 holiday 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. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Highland Mills.
  2. Plan your budget wisely: On top of the price of your stay, you should factor in other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Highland Mills.
  3. Set the duration of your trip: Start by listing all the activities and sights you want to get to in Highland Mills. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your accommodation and airfare: Once you've settled on your trip dates and duration, book the ideal Highland Mills holiday package for you.

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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.