Town of Highlands Holiday Rentals from €112: Search Short-Term Rentals

A suspension bridge over a river with a sunset in the background.

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Our top choices for Town of Highlands holiday rentals

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Highland Falls

Maria L.

includes taxes & fees

7 Jul - 8 Jul

House on the Babbling Brook- Quiet 2BR + King Bed!

Highland Falls

Scott G.

includes taxes & fees

2 Jul - 3 Jul

Lovely 3BR Home with parking-Walk to WP Gate!

Highland Falls

Briana T.

includes taxes & fees

7 Jul - 8 Jul

Fabulous 3bdrm Home w/parking!

Highland Falls

Danielle B.

includes taxes & fees

14 Jul - 15 Jul

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery

Meredith C.

includes taxes & fees

6 Jul - 7 Jul

Cozy 1-bedroom retreat minutes from West Point!

Highland Falls

Zack C.

includes taxes & fees

28 Jul - 29 Jul

3BR West Point Retreat-3min to Back Gate+ King Bed

Highland Falls

Christine T.

includes taxes & fees

6 Jul - 7 Jul

Walk to WP Gate + Free Parking!

Highland Falls

Jodi P.

includes taxes & fees

23 Jul - 24 Jul

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Top Town of Highlands Hotel Reviews

Armoni Inn & Suites

10/10 Excellent

"Good"

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent

"My family and I had a wonderful stay here! It was conveniently located close to LEGOLAND, which made our trip so much easier. The boys absolutely loved the pool, and the complimentary breakfast was surprisingly phenomenal with plenty of great options. The gym was perfect for me to do a bit of strength training.Every staff member we encountered was friendly, welcoming, and very helpful. We would definitely stay here again!"

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent

"AMAZING HOTEL!! if you need a place to stay for a night or two definitely choose this one! clean, nice quality, spacious affordable room, nice bathroom, nice indoor pool a& gym and inclusive breakfast! I often go back and forth to this area so I will be back!"

Hotel Nyack, a JdV by Hyatt Hotel

8/10 Good

"I gave this property a "Good" rating instead of an "Excellent" because the customer service was lacking. Our room was not ready at 4:30pm. We were offered a drink voucher and I had to remind the front desk that there were two of us in the room. When we did get into our room several items were missing. The ottoman that was supposed to accommodate our suitcases was not there. The hairdryer was also missing. The front desk did have someone bring these items but I felt that there was a real "Oh well" feeling about our stay. That said the hotel is unique and appears to be a repurposed industrial building with very interesting and minimalist decor. It was clean both in our room as well as the common areas. The Hyatt is conveniently located and appears to be the only upscale hotel in the area."

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Holiday Homes in Town of Highlands

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Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Town of Highlands holiday rentals

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

House on the Babbling Brook- Quiet 2BR + King Bed!