The Best Historic Hotels in Highland, NY from NT$3,543 in 2026

A suspension bridge over a river with autumn foliage and distant hills.

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Standard Room, 2 Queen Beds, Non Smoking, Refrigerator (with Sofabed) | Desk, laptop workspace, blackout drapes, soundproofing

SureStay Plus Hotel by Best Western Highland Poughkeepsie

Highland

Michael

NT$3,807 total

includes taxes & fees

Aug 16 - Aug 17

Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

Charlie

NT$4,026 total

includes taxes & fees

Aug 4 - Aug 5

Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

Kenice

NT$3,543 total

includes taxes & fees

Aug 30 - Aug 31

Hampton Inn & Suites Poughkeepsie

Crown Heights

Quincy

NT$4,285 total

includes taxes & fees

Aug 30 - Aug 31

DoubleTree by Hilton Poughkeepsie Convention Center

Downtown Poughkeepsie

James

NT$4,287 total

includes taxes & fees

Aug 30 - Aug 31

Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

Genevieve Xyra

NT$5,235 total

includes taxes & fees

Aug 18 - Aug 19

Homewood Suites by Hilton Poughkeepsie

Poughkeepsie

Audie

NT$5,214 total

includes taxes & fees

Aug 9 - Aug 10

Americas Best Value Inn New Paltz

New Paltz

Michael

NT$4,238 total

includes taxes & fees

Aug 30 - Aug 31

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Top Highland Hotel Reviews

Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent

"This location had everything we needed, and it felt safe. Cleanliness was an A+, and amenities included great coffee, a complimentary breakfast, and parking l. Definitely will be returning to this hotel on my next trip to Poughkeepsie"

Beekman Arms and Delamater Inn

8/10 Good

"This is a lovely inn. I have always wanted to stay here. The bar was great. The food was amazing. However, the wifi did not function in my room. The check in staff did not inform me that coffee would be available in the lobby in the morning. Frankly, I found him somewhat condescending. The property is beautiful, the setting is fantastic. There was a window air conditioner. I did not stay around for breakfast as I wanted to get home. I believe the rumors about the Inn being haunted to be true. I was awakened in the night by someone whispering "Hey" in my ear. Just a fun observation."

SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent

"They were SUPER dog friendly which was great to see and we could walk around the property to give our pup some exercise and others were doing the same. It was very clean and very comfortable and everything we needed and looking for."

Frequently asked questions

What should a history buff expect from a stay in Highland?

The historical places in Highland are likely a big part of your travel plans. While you are here in this family-friendly area, why not also discover all of the sights in the area?

How many historical hotels are there in Highland?

In Highland, you'll find 39 hotel accommodations bookable on Expedia but not many designated as historic hotels.

What are the top historical sites and other places to visit in Highland?

Highland is notable for landmarks like Walkway Over the Hudson State Historic Park. A couple of additional sights to add to your agenda are Franklin D Roosevelt Library & Museum and Apple Greens Golf Course.

What is a historic hotel like in Highland?

Guests who book a historic hotel can stay in a building that has an officially recognized historic designation. A stately home, palace or even a lodge, old police station, or skyscraper can be identified as a historic hotel as long as it's of special interest. Traditional architecture and period features are often preserved in the communal spaces and guestrooms of historic hotels in Highland, giving a historical feel.

What is the difference between a historic hotel and a heritage hotel?

"Heritage hotel" is more common in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. but overall the terms are quite similar. The physical building and architecture of historic hotels tend to be what's most important. For a heritage hotel, it's mainly the cultural value and how it shaped the community.

Do historic hotels in Highland have modern facilities?

Hotels include modern conveniences and safety features you've come to expect, though efforts have been made to preserve treasured traditions and historic facades. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the popular amenities found at a contemporary hotel will be available in a historic hotel. When you choose a historic hotel in Highland, don't worry that you'll find a place that's uncomfortable for guests or simply rundown.

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