Photo by Karen Wirtz

Hotels in Highland

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Check prices for these dates

Tonight
May 6 - May 7
Tomorrow
May 7 - May 8
This weekend
May 9 - May 11
Next weekend
May 16 - May 18

Where to stay in Highland?

SureStay Plus Hotel by Best Western Highland Poughkeepsie
Front of property

SureStay Plus Hotel by Best Western Highland Poughkeepsie

2.5 star property
7.6 out of 10, Good, (820)
The price is $118
includes taxes & fees
$105 per night
May 7 - May 8
SureStay Plus Hotel by Best Western Highland Poughkeepsie
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.
trending_down

Our prices for hotels in Highland are cheapest in December

See average prices and weather for all months

Price trends for hotels in Highland

Pricing is based on two traveler single night rates
May
$181
Average price during May is $181
Jun
$181
Average price during June is $181
Jul
$167
Average price during July is $167
Aug
$182
Average price during August is $182
Sep
$208
Average price during September is $208
Oct
$209
Average price during October is $209
Nov
$124
Average price during November is $124
Dec
$103
Average price during December is $103
Jan
$109
Average price during January is $109
Feb
$109
Average price during February is $109
Mar
$124
Average price during March is $124
Apr
$123
Average price during April is $123
Currently viewing crowd sizes and weather for May.

May

trending_flatModerate crowds
High 70°F / low 49°F. Sunny most days.
70°
weather_sun
May, Moderate crowds, average high temperature 70 degrees Fahrenheit, average low temperature 49 degrees Fahrenheit. Sunny most days.
49°
78°
weather_sun
June, High crowds, average high temperature 78 degrees Fahrenheit, average low temperature 56 degrees Fahrenheit. Sunny most days.
56°
84°
weather_sun
July, Moderate crowds, average high temperature 84 degrees Fahrenheit, average low temperature 63 degrees Fahrenheit. Sunny most days.
63°
82°
weather_sun
August, High crowds, average high temperature 82 degrees Fahrenheit, average low temperature 61 degrees Fahrenheit. Sunny most days.
61°
75°
weather_sun
September, High crowds, average high temperature 75 degrees Fahrenheit, average low temperature 55 degrees Fahrenheit. Sunny most days.
55°
62°
weather_sun
October, High crowds, average high temperature 62 degrees Fahrenheit, average low temperature 45 degrees Fahrenheit. Sunny most days.
45°
49°
weather_partly_sunny
November, Moderate crowds, average high temperature 49 degrees Fahrenheit, average low temperature 33 degrees Fahrenheit. Partly sunny.
33°
39°
ac_unit
December, Low crowds, average high temperature 39 degrees Fahrenheit, average low temperature 27 degrees Fahrenheit. Snow likely.
27°
34°
ac_unit
January, Low crowds, average high temperature 34 degrees Fahrenheit, average low temperature 20 degrees Fahrenheit. Snow likely.
20°
37°
ac_unit
February, Low crowds, average high temperature 37 degrees Fahrenheit, average low temperature 20 degrees Fahrenheit. Snow likely.
20°
46°
weather_partly_sunny
March, Low crowds, average high temperature 46 degrees Fahrenheit, average low temperature 28 degrees Fahrenheit. Partly sunny.
28°
58°
weather_partly_sunny
April, Moderate crowds, average high temperature 58 degrees Fahrenheit, average low temperature 38 degrees Fahrenheit. Partly sunny.
38°
Monthly weather averages (˚F)
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Top landmarks in Highland

Franklin D Roosevelt Library & Museum

If visiting museums in Highland are on your list, you might want to check out the upcoming exhibitions at Franklin D Roosevelt Library & Museum. Our travelers also like this historical area for its riverfront setting. If you want to see more of the museums in Highland, Vanderbilt Mansion National Historic Site and Franklin D. Roosevelt Presidential Library and Museum aren't far.

See properties in Franklin D Roosevelt Library & Museum
Franklin D Roosevelt Library & Museum

Learn more about Highland

Highland is well-known for its attractions such as Walkway Over the Hudson State Historic Park and Berean Park Beach. This family-friendly city has something for everyone including sights like Franny Reese State Park and Franklin D Roosevelt Library & Museum within a sunny setting.

See all hotels in Highland
View from Walkway over the Hudson
Photo by Karen Wirtz
Open Photo by Karen Wirtz
A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

Summer Getaway Sale

Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
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Frequently asked questions

What hotels do travelers like in Highland?
SureStay Plus Hotel by Best Western Highland Poughkeepsie and Rodeway Inn & Suites New Paltz - Hudson Valley are a couple of properties that our guests really like.
Can I book a refundable hotel in Highland?
If you need the flexibility to change your travel plans to Highland, most properties provide refundable* bookable rates. You can see these properties by searching our site and using the “fully refundable” filter to narrow down the results.
Where can I stay with my pet in Highland?
Your animal companion is welcome at this pet-friendly hotel: SureStay Plus Hotel by Best Western Highland Poughkeepsie.
Which Highland hotels do our guests like for their central location?
Our guests love SureStay Plus Hotel by Best Western Highland Poughkeepsie for its great location.
Where should I stay in Highland if I want a budget-friendly accommodation?
An inexpensive option worth considering is SureStay Plus Hotel by Best Western Highland Poughkeepsie.
Where can I stay in Highland if I want a vacation rental instead of a hotel?
If you want to find a good alternative to a hotel, review our selection of 20 vacation homes. In addition, you can choose from 7 apartments.
Where can I stay if I'm traveling to Highland with my kids?
Parents traveling with children may want to consider Rodeway Inn & Suites New Paltz - Hudson Valley.
What will the weather in Highland be like during my trip?
July and August are typically the warmest months in Highland when the average temp is 69°F. January and February are the coldest months when the average temperature is 31°F. October and December are the months with the most rain.
Why should I book my Highland hotel through Hotels.com?
There are lots of reasons to book your Highland trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

OneKeyCash is not redeemable for cash and can only be used on Hotels.com®, Expedia®, and Vrbo®.

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