Highland Mills Holidays

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Top Flight + Hotel Deals in Highland Mills

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Save 100% on your flight
Price was €1,370, price is now €910 per person
€910
per person
3 Sept - 7 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (7,519 reviews)
I love this hotel! Start here every time. The housekeeper Norma is lovely. The staff is always so helpful and nice. I always feel safe here.

Reviewed on 14 Jul 2026

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Save 100% on your flight
Price was €1,884, price is now €1,115 per person
€1,115
per person
16 Sept - 21 Sept
found 9 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
8/10 Very good! (2,471 reviews)
Great place to stay for the price!

Reviewed on 14 Jul 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was €1,817, price is now €1,192 per person
€1,192
per person
3 Sept - 7 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (3,130 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was €1,733, price is now €1,148 per person
€1,148
per person
3 Sept - 7 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,652 reviews)
Managed to get us a room on extremely short notice. Fantastic place, great staff, and located right in the heart of Manhattan!

Reviewed on 14 Jul 2026

The Ridge Hotel

The Ridge Hotel

3 out of 5
Manhattan
Save 100% on your flight
Price was €1,574, price is now €1,086 per person
€1,086
per person
16 Sept - 21 Sept
found 9 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
8.2/10 Very good! (1,156 reviews)
The air conditioning was awesome! My room was set at 63 and it was great. The fridge was cold as well. No hair dryer or hangers, had to ask for them. Room seemed clean enough but my remote control was so gross, looked like it was cleaned for years. There was dust over window sills and on top of hooks.

Reviewed on 14 Jul 2026

Top hotels in Highland Mills

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 €127 per night from 2 Aug to 3 Aug
€127
2 Aug - 3 Aug
includes taxes & fees
8.8/10 Excellent! (1,077 reviews)
"The breakfast was excellent and the rooms were lovely. The pool is disappointing because it is super tiny and there was a private group swim lesson while we were there which took up half the space."

Reviewed on 13 Jul 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 €120 per night from 27 Jul to 28 Jul
€120
27 Jul - 28 Jul
includes taxes & fees
9/10 Wonderful! (1,024 reviews)
"Overall, the property was nice and clean. Although a bit noisy no doubt from the pipes. But also because of a yapping dog in a nearby room"

Reviewed on 14 Jul 2026

Hyatt Place Poughkeepsie / Hudson Valley
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is €91 per night from 2 Aug to 3 Aug
€91
2 Aug - 3 Aug
includes taxes & fees
8.4/10 Very good! (164 reviews)
"Clean and quiet. Comfortable room and bed"

Reviewed on 14 Jul 2026

Spark by Hilton Fishkill
See all 850 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

Frequently asked questions

How much does a Highland Mills holiday package cost?
You'll find cheap prices from €910 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.