Name: Courtyard by Marriott Poughkeepsie
Price range: CA $144
Rating: 8.8

Your Highland Vacation

Reserve a Highland vacation package and get set to experience all this city has to offer. Consider basing yourself in the neighborhood of Poughkeepsie Waterfront, which is great for families, history and culture. If sightseeing is on the to-do list during your trip to Highland, swing by well-known attractions like Walkway Over the Hudson State Historic Park, Franklin D Roosevelt Library & Museum and Apple Greens Golf Course. Check out Expedia's wide range of travel options and book your dream vacation to Highland now.

Top Highland Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Hotel St. James

Manhattan

CA $834

per person

Apr 18 - Apr 21

found 2 hours ago

Roundtrip flight included

Toronto (YTO) to Newark Liberty Intl. Airport (EWR)

8.8/10 Excellent! (6,546 reviews)

Clean room safe location

Reviewed on Feb 8, 2026

Arthouse Hotel New York City

Manhattan

CA $1,441

per person

Mar 14 - Mar 21

found 1 hour ago

Roundtrip flight included

Toronto (YTO) to Newark Liberty Intl. Airport (EWR)

8.8/10 Excellent! (1,678 reviews)

Hip boutique hotel with an industrial cozy vibe. Rooms are sumple but have everything you need. The libby bar and cafe are nice. Attached to Serafina restaurant. Great lication overall and parking across the street.

Reviewed on Feb 6, 2026

1 Hotel Central Park

Manhattan

CA $2,010

per person

Apr 25 - Apr 29

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,001 reviews)

Excellent stay! Friendly staff, comfortable, beautiful rooms & lobby.

Reviewed on Feb 2, 2026

The Fifth Avenue Hotel

Manhattan

CA $2,194

per person

Apr 25 - Apr 29

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Newark Liberty Intl. Airport (EWR)

9.6/10 Exceptional! (159 reviews)

Staff were lovely, helpful and pleasant. Turndown service way too late, though—9:45 might catch some guests sleeping.

Reviewed on Jan 3, 2026

Hyatt Regency Jersey City on the Hudson

Downtown Jersey City

CA $2,049

per person

Apr 26 - May 2

just found

Roundtrip flight included

Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)

8.4/10 Very Good! (1,565 reviews)

We loved to stay here but hotel wifi is too mush slow and some the telephone doesn’t work.all other the staff was so good and nice rooms.

Reviewed on Feb 8, 2026

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Highland Hotel Deals

SureStay Plus Hotel by Best Western Highland Poughkeepsie

3423 US Highway 9W Highland NY

Fully refundableReserve now, pay when you stay

CA $103

CA $116 total

Feb 12 - Feb 13

includes taxes & fees

7.6/10 Good! (960 reviews)

Super clean! Hotel manager along with all other employees were pleasant and helpful.

Reviewed on Feb 6, 2026

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Highland NY

9.4/10 Exceptional! (11 reviews)

Great place to stay! Communication was great, beds are SUPER comfortable and the separate heating/cooling in each room is nice. The living room doesn't have enough seeing for it to be the hangout spot, so lots of kitchen conversations :) The piano was a fun addition and we had some fun musical moments. ...

Reviewed on Nov 25, 2025

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Courtyard by Marriott Poughkeepsie

2641 South Road/Route 9 Poughkeepsie NY

Fully refundableReserve now, pay when you stay

CA $144

CA $162 total

Feb 17 - Feb 18

includes taxes & fees

8.8/10 Excellent! (1,008 reviews)

Very friendly, kind staff and clean room

Reviewed on Feb 2, 2026

See all 1,534 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.