Highland Mills Vacations

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Find the Best Highland Mills Vacation Packages

Highland Mills Hotel Deals

HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is NT$3,277 per night from Jul 13 to Jul 14
NT$3,277
NT$3,707 total
Jul 13 - Jul 14
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Nothing"

Reviewed on 2025/6/23

HYATT house Fishkill/Poughkeepsie
Hampton Inn & Suites Poughkeepsie
Hampton Inn & Suites Poughkeepsie
2.5 out of 5
2361 South Rd, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is NT$3,261 per night from Jul 9 to Jul 10
NT$3,261
NT$3,787 total
Jul 9 - Jul 10
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Great room"

Reviewed on 2025/6/24

Hampton Inn & Suites Poughkeepsie
Best Western The Inn At Ramsey
Best Western The Inn At Ramsey
3 out of 5
1315 Route 17 South, Ramsey, NJ
Fully refundableReserve now, pay when you stay
The price is NT$2,760 per night from Jul 9 to Jul 10
NT$2,760
NT$3,164 total
Jul 9 - Jul 10
includes taxes & fees
7.2/10 Good! (1,003 reviews)
"N/A"

Reviewed on 2025/6/14

Best Western The Inn At Ramsey
See all 773 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.

Frequently asked questions

How much does a Highland Mills vacation package cost?
You'll find cheap prices 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?
January, February and March are the best times to look for cheap Highland Mills vacation 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 vacation 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 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. 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 accommodations and airfare: Once you've settled on your trip dates and duration, book the ideal Highland Mills vacation package for you.

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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.