Highland Hotels

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We use indicative prices on this page to help you choose from a large number of options. The prices on this page are indicative estimates based on searches conducted by travelers on Skyscanner, which are subject to change.
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Fast facts

Sleep easy, armed with the stuff that's good to know before you go.
Highest-rated hotelHyatt Place Poughkeepsie / Hudson Valley – 4.5
Cheapest month to bookMay

Your guide to finding the best hotels in Highland, New York

To make the most of your time in Highland, reserve a hotel that’s right for you. We’ve gathered some of the city’s best hotels, from luxury to budget-friendly.

Best time to visit Highland

Highland is an interesting travel destination year-round, but what you hope to do (or avoid) during your vacation should be considered while making plans, such as weather and price. Low and high season in Highland

Busiest month(s): Highland experiences its peak tourist season in August, bringing an average nightly rate of $226. For those booking a vacation during this period, it's essential to account for higher costs compared to slower times of the year, which offer average nightly prices as low as $169.

Quietest month(s): Save on your hotel stay and avoid peak season prices by visiting during July, when the average rate per night is $169.

The priciest month in Highland is August, and you can expect to spend around $226 on hotels. Weekend rates usually increase, averaging around $174 per night throughout the year, and Saturday bookings cost the most at the best hotels in Highland. You'll find savings on Sunday, which is the cheapest day to reserve a room on average.

Where to stay in Highland, New York

With Skyscanner, it's easy to find the best Highland hotels — from 5-star to the most booked — at a cost you want.

Popular hotels in Highland

The Black Creek Bed And Breakfast, Inn at Twaalfskill, Rocking Horse Ranch Resort, SureStay Plus Hotel by Best Western Highland Poughkeepsie, and Americas Best Value Inn - HighlandPoughkeepsie are just some of the hotels available to you in Highland, providing plenty of services and amenities to make your stay a comfortable one.

Things to do in Highland

Many Highland sites take you right to the heart of the city, like the Lilly Rae In The Hamlet. If you're a foodie, you'll enjoy the authentic local cuisine, creative twists on classics, and flavors from around the world at Vigneto Cafe Restaurant, Gunk Haus Restaurant, Underground Coffee & Ales, Coppola's La Fantasia, and Gateway Diner.

Finding cheap hotels in Highland: FAQs

You can always cancel or amend your hotel reservation if you need to, but look out for hotels in Highland with free cancellation or flexible booking options if you want to protect your money. Some hotels allow you to cancel and get your money back if your plans change.
Of course, the cheapest hotel deal we found within the next seven days is C$150 per night. If you need somewhere in the next 24 hours, we've found you somewhere to stay for C$157 per night.
The average price of a hotel during the week is C$171 per night, and the average price on weekends is C$230. Overall, it looks like the cheapest day to stay in Highland could be Monday.
We crunched some numbers on our calendar and found that Monday is the cheapest day to stay in Highland, and the most expensive day seems to be Saturday.
If you're hitting up Highland with kids in tow, try Holiday Inn Express Poughkeepsie, or Courtyard Poughkeepsie.