Highland, NY

Travel Guide

A suspension bridge over a river with autumn foliage and distant hills.
A mountainous landscape with a clear sky and scattered clouds.
A large suspension bridge spanning a wide river, surrounded by hills and a train track running parallel to the riverbank.
A suspension bridge over a river with hills in the background.
SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

2.5 out of 5
3423 US Highway 9W Highland NY
$80 nightly
The price is $90 total per night from Nov 12 to Nov 13
$90 total
Nov 12 - Nov 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Highland. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
SureStay Plus Hotel by Best Western Highland Poughkeepsie
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
$94 nightly
The price is $109 total per night from Nov 29 to Nov 30
$109 total
Nov 29 - Nov 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hyatt Place Poughkeepsie / Hudson Valley
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

2.5 out of 5
835 Route 52 Fishkill NY
$98 nightly
The price is $113 total per night from Nov 29 to Nov 30
$113 total
Nov 29 - Nov 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,005 reviews)
"We enjoyed our stay. It was remarkably quiet. No road noise, no noise from neighboring rooms!"

Reviewed on Nov 7, 2026

Comfort Suites Fishkill near Interstate 84
See all 1,531 properties in Highland
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.
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Highland NY
Book a stay at this family-friendly vacation home in Highland. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Apple Greens Golf Course ...
9.6/10 Exceptional! (14 reviews)
"House was awesome Spacious, clean, great yard Host communication was great"

Reviewed on Oct 22, 2026

Our home is perfect for relaxing and having lots of fun, with near by activity’s
The Scenic Mansion With Breathtaking View

The Scenic Mansion With Breathtaking View

Highland NY
Stay at this villa in Highland. Enjoy private pools, laundry facilities, and tennis courts. Popular attractions Franny Reese State Park and Mid-Hudson Bridge ...
8/10 Very Good! (24 reviews)
"This property sits on the top of a hill and offers great views over the countryside. The exterior of the property offers a nice tennis court but it has poison ivy around the perimeter and actually inside the court's fence making retrieving balls hazardous, a nice swimming pool, and outdoor furniture ..."

Reviewed on Aug 24, 2026

The Scenic Mansion With Breathtaking View
Private 4BR Mountain View Retreat Near New Paltz

Private 4BR Mountain View Retreat Near New Paltz

Highland NY
Book a stay at this golf vacation home in Highland. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Apple Greens Golf Course and Jenkinstown ...
10/10 Exceptional! (36 reviews)
"Absolutely beautiful, clean, peaceful house with plenty of room for 7 adults."

Reviewed on Nov 4, 2026

Private 4BR Mountain View Retreat Near New Paltz
See all properties in Highland
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 attractions

Franny Reese State Park

You can take time to visit Franny Reese State Park during your travels to Highland. Stroll along the riverfront or discover the mountain views in this family-friendly area.
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Frequently asked questions

Is Highland worth visiting?
Highland is worth visiting for its notable attractions, including the Franklin D Roosevelt Library & Museum and the Apple Greens Golf Course. Travelers can also enjoy a diverse culinary scene, with options ranging from Italian to North American dining, offering a variety of flavors to explore.
When is the best time to visit Highland?
The best time to visit Highland is from March through May, when the weather is typically pleasant for exploring. For travelers seeking fewer crowds and better value, the quieter months of November through January are a good option, offering a more relaxed experience.
What is Highland known for?
Highland is known for the Franklin D Roosevelt Library & Museum, offering insights into presidential history. Travelers can also enjoy the Apple Greens Golf Course and relax at Berean Park Beach. The area also features a strong Italian food culture, providing diverse dining options.
What is a good itinerary length for Highland?
A good itinerary length for Highland is two to three days to explore the Franklin D Roosevelt Library & Museum, enjoy Apple Greens Golf Course, and relax at Berean Park Beach. For an extended trip of four to five days, travelers can revisit these spots or simply enjoy the local atmosphere at a more leisurely pace.
What are the top things to do in and around Highland?
In Highland, travelers can explore historical sites, enjoy outdoor activities, and relax at a beach:


How do I plan a trip to Highland?
To plan your trip to Highland, book flights and hotels in advance. Explore attractions such as the Franklin D Roosevelt Library & Museum, Apple Greens Golf Course, and Berean Park Beach. Remember to pair outdoor plans with indoor backups for weather flexibility. Consider a rental car for exploring, and enjoy Italian, North American, or Latin American dining.
What cuisines can you find in Highland?
In Highland you can find German cuisine, with dishes like bratwurst, schnitzel, and pretzels. Travelers can also enjoy Italian, North American, and Latin American options, including Mexican and taco specialties. Asian cuisine, featuring Chinese, Japanese, and Vietnamese dishes, along with Mediterranean flavors, are also available.
Can I book a refundable hotel in Highland?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Highland by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Highland with Expedia?
Expedia makes it easier to plan your Highland trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Highland?
The best choice depends on your travel style. Hotels in Highland can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Highland trip on Expedia?
Once you've booked your Highland trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Highland trip?
Expedia offers customer support before, during, and after your Highland trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Highland?
If it's your first trip to Highland, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Highland hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Highland hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Highland

A street with brick buildings, a red car, and a white SUV.

New Paltz

A house with a stone foundation, a gabled roof, and a large bay window.

Hyde Park

A river with boats docked on the shore, surrounded by autumn-colored trees.

Poughkeepsie

A forested landscape with a mist-covered hill and a clear sky.

Marlboro

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