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Boutique Hotels & Resorts in Highland from AU$135

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Recommended hotels in Highland

Terrace/patio
Homewood Suites by Hilton Poughkeepsie

Homewood Suites by Hilton Poughkeepsie

Homewood Suites by Hilton Poughkeepsie
3.0 star property
Poughkeepsie
9.6 out of 10, Exceptional, (1003)
"Room was very large and hotel had everything we needed"
United States
Cassie
The price is AU$214
includes taxes & fees
28 Dec - 29 Dec
Homewood Suites by Hilton Poughkeepsie
Books, music library, stereo
Twin Gables of Woodstock

Twin Gables of Woodstock

Twin Gables of Woodstock
3.0 star property
Woodstock
9.8 out of 10, Exceptional, (192)
"Amazing stay!!! Super hippie vibe and lived every minute of it. "
United States
Heather
The price is AU$218
includes taxes & fees
21 Dec - 22 Dec
Twin Gables of Woodstock
Exterior detail
The Herwood Inn

The Herwood Inn

The Herwood Inn
4.5 star property
Woodstock
9.6 out of 10, Exceptional, (90)
"Just lovely all around! I loved the attention to detail inside and on the grounds."
United States
karen
The price is AU$322
includes taxes & fees
12 Jan - 13 Jan 2026
The Herwood Inn
Reception
SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie
2.5 star property
Highland
7.8 out of 10, Good, (947)
"Was a great stay! "
United States
Alane
The price is AU$135
includes taxes & fees
4 Jan - 5 Jan 2026
SureStay Plus Hotel by Best Western Highland Poughkeepsie
Bar (on property)
The Thayer Hotel at West Point

The Thayer Hotel at West Point

The Thayer Hotel at West Point
3.5 star property
West Point
9.0 out of 10, Wonderful, (667)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
The price is AU$277
includes taxes & fees
25 Dec - 26 Dec
The Thayer Hotel at West Point
Exterior
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG
2.5 star property
Poughkeepsie
8.6 out of 10, Excellent, (1000)
"Clean room, nice amenities, great service, amazing staff"
United States
Xavier
The price is AU$177
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Express Poughkeepsie by IHG
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie
3.0 star property
Fishkill
8.8 out of 10, Excellent, (1000)
"Centrally located to all Bethel locationswith many dining options nearby. Always felt safe and breakfast was delicious."
United States
Mireyma
The price is AU$200
includes taxes & fees
18 Jan - 19 Jan 2026
HYATT house Fishkill/Poughkeepsie
Front of property
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn
3.5 star property
Rhinebeck
8.4 out of 10, Very good, (807)
"I’ve stayed at the Beckman Arms many times, in all of the various parts (motel, Delamater House, etc) and have never been disappointed. The location is exceptional, the rooms are cozy and clean, and parking is great. I highly recommend it if you’re staying in the area."
United States
Armand
The price is AU$176
includes taxes & fees
1 Jan - 2 Jan 2026
Beekman Arms and Delamater Inn
Terrace/patio
Home2 Suites By Hilton Poughkeepsie

Home2 Suites By Hilton Poughkeepsie

Home2 Suites By Hilton Poughkeepsie
3.0 star property
Poughkeepsie
9.4 out of 10, Exceptional, (392)
"Beautiful room and great staff! Would stay here again. "
United States
Christina
The price is AU$190
includes taxes & fees
23 Dec - 24 Dec
Home2 Suites By Hilton Poughkeepsie
Superior Room, Fireplace, River View
Woodstock Way Hotel

Woodstock Way Hotel

Woodstock Way Hotel
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (216)
"The room and views were lovely, and we loved the Tannery cafe!"
United States
Katherine
Woodstock Way Hotel
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.
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Top Highland Hotel Reviews

Frequently asked questions

What's there to see and do in Highland?
Once you've decided where to stay in family-friendly Highland, figure out some fun things to do on your trip. Walkway Over the Hudson State Historic Park, Franklin D Roosevelt Library & Museum and Mid-Hudson Bridge are some of the local sights worth visiting. You might also like to explore more of the area and take in additional sights like Mid-Hudson Civic Center, Bardavon 1869 Opera House and Home of Franklin D. Roosevelt National Historic Site while you're here.
What kind of weather should I plan for when I travel to Highland?
Getting an idea of what to expect from the weather in Highland is important when planning your trip. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Highland are January, February, March and April, with each month seeing an average of 17 cm of snowfall.
What's the best way to get to my boutique hotel in Highland?
You have a few options for travelling to and around Highland. The closest major airport is Newburgh, NY (SWF-Stewart Intl.), which is located 16.6 mi (26.7 km) from the heart of the city. If you'd like to venture out around the area, you may want a rental car for your journey.

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