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 1 to Nov 2
$90 total
Nov 1 - Nov 2
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 15 to Nov 16
$109 total
Nov 15 - Nov 16
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
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
$169 nightly
The price is $191 total per night from Nov 9 to Nov 10
$191 total
Nov 9 - Nov 10
Total with taxes and fees
Book a stay at this business-friendly inn in Rhinebeck. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.2/10 Very Good! (1,001 reviews)
"Charming hotel in center of Rhinebeck"

Reviewed on Oct 14, 2026

Beekman Arms and Delamater Inn
See all 1,558 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.
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 37 Acre Lake Estate on 164 Acres - 11 BR

Private 37 Acre Lake Estate on 164 Acres - 11 BR

Highland NY
Stay at this vacation home in Highland. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Hyde Park Station and Hyde Park Landing are located ...
9.4/10 Exceptional! (3 reviews)
Beautiful property, great for a large group
"We spent Christmas here with friends and family and enjoyed our stay. Everything we needed was there. We were only disappointed in the communication with the property manager due to the holiday and technical issues. If you stay in the winter make sure the fireplace has been serviced as the smoke ..."

Reviewed on Dec 26, 2024

Private 37 Acre Lake Estate on 164 Acres - 11 BR
2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen

Fishkill NY
Stay at this apartment in Fishkill. Enjoy free WiFi, cable/satellite TV service, and air conditioning. Popular attractions Van Wyck Homestead Museum and Fishkill ...
8.4/10 Very Good! (25 reviews)
"Arrived with paid reservation -no rooms available......not a legit business. The sister hotel in the area had same issue earlier this year. I will not return."

Reviewed on Sep 20, 2026

2 Queen Beds | Non-Smoking, Kitchen
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.

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