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

Vacation Rentals in Town of Highlands

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Our top choices for Town of Highlands vacation rentals

A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

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

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (13 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is ￥20,264
￥64,551 total
includes taxes & fees
Oct 14 - Oct 15
House on the Babbling Brook- Quiet 2BR + King Bed!
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

2. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is ￥18,206
￥48,581 total
includes taxes & fees
Oct 14 - Oct 15
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A house with a view of a bridge and mountains.

3. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (148 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥31,345
￥52,174 total
includes taxes & fees
Oct 20 - Oct 21
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A hallway with a wooden door, a black table with a sign, and large green plants.

4. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay at Joseph’s home. The property was very clean, spacious, and well prepared for guests. My work team and I felt comfortable right away, and the house had everything we needed for both a productive and relaxing stay.Joseph was always kind, professional, and quick to respond, which made a big difference. I would recommend this property without hesitation."
United States
ROHID S.
The price is ￥20,739
￥69,867 total
includes taxes & fees
Oct 14 - Oct 15
3BR Near West Point | Coffee Bar | Sleeps 6
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

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

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
The price is ￥34,242
￥57,571 total
includes taxes & fees
Nov 9 - Nov 10
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A wooden coffee table with two decorative planters in a living room.

6. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
The price is ￥38,398
￥62,920 total
includes taxes & fees
Nov 9 - Nov 10
Walk to WP Gate + Free Parking!
Living area

7. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is ￥19,615
￥36,391 total
includes taxes & fees
Nov 9 - Nov 10
Cozy 1-bedroom retreat minutes from West Point!
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

8. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (20 reviews)
The price is ￥22,502
￥71,827 total
includes taxes & fees
Nov 2 - Nov 3
Local Artist Inspired | Walk to WestPoint + King Bed
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

9. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
The price is ￥25,488
￥76,188 total
includes taxes & fees
Nov 2 - Nov 3
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

10. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
The price is ￥39,229
￥65,482 total
includes taxes & fees
Nov 9 - Nov 10
Fabulous 3bdrm Home w/parking!
The exterior of Highland Falls Library with a white facade, two wooden benches in front, and a sign above the entrance.

11. Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi

Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
Highland Falls
9.6 out of 10, Exceptional, (36 reviews)
"Good location and had a great stay!"
United States
James M.
The price is ￥78,997
￥131,182 total
includes taxes & fees
Oct 14 - Oct 15
Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
A blue house with a white porch, a welcome sign, and a mailbox.

12. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is ￥23,747
￥79,596 total
includes taxes & fees
Oct 14 - Oct 15
3BR West Point Retreat-3min to Back Gate+ King Bed
A room with a wooden floor, a white door with a number, and a window with blinds.

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

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is ￥37,068
￥66,807 total
includes taxes & fees
Nov 9 - Nov 10
Lovely 3BR Home with parking-Walk to WP Gate!
A spacious loft with a high ceiling, exposed beams, a kitchen with modern appliances, a dining area, and a living room with a large sofa.

14. Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
10.0 out of 10, Exceptional, (3 reviews)
"This location was perfect for our yearly fall gathering. It is 15 minutes from Pure Terror Scream Park and nestled in a historic town. The unit was clean, spacious, and perfect for a group of 7-8 people. The hosts were very helpful and prompt with instructions. I would recommend this stay if you are looking to stay in Goshen, NY."
United States
Tammy
Hay Loft Apartment in Barn - Goshen
A modern kitchen with dark cabinets, a stainless steel stove, and a wooden countertop.

15. Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
10.0 out of 10, Exceptional, (1 review)
Carriage House Apartment Goshen NY
A living room with a fireplace, a painting, shelves with decorative items, and a television.

16. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (50 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
The price is ￥21,372
￥46,743 total
includes taxes & fees
Nov 2 - Nov 3
Grant - A Tranquil One Bedroom Steps from River
A brick building with a sign reading 'Lobby' in front.

17. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (20 reviews)
"Great place to stay,"
United States
Anonymous traveler
The price is ￥12,482
￥14,432 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

18. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (41 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is ￥35,620
￥64,641 total
includes taxes & fees
Oct 14 - Oct 15
Contemporary Cozy Cottage
A deck with Adirondack chairs, a fire pit, and a grill.

19. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Cornwall
10.0 out of 10, Exceptional, (15 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is ￥34,512
￥69,006 total
includes taxes & fees
Nov 2 - Nov 3
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
A spacious living room with a stone fireplace, two white sofas, a glass coffee table, and large windows.

20. Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (13 reviews)
"The breakfast was lovely!"
United States
Tara
The price is ￥34,828
￥44,415 total
includes taxes & fees
Nov 1 - Nov 2
Villa Verde B&B, bsm, Greenwood Lake NY
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Town of Highlands Hotel Reviews

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

10/10 Excellent
"The hotel wasn't fancy or anything but it was perfect for a quick visit. The rooms were clean and spacious. It was close to many food places and there was a decent amount of parking. I would recommend"
Kellie 1-night trip
Posted 1 hour ago
Comfort Suites Fishkill near Interstate 84

Find out more about Town of Highlands

Vacation Apartments in Town of Highlands

Search for Vacation rentals in Town of Highlands on Expedia! You can easily find your home rentals, villas, Vacation apartments in Town of Highlands using one of the methods below:

  • View our selection of featured Vacation rentals in Town of Highlands
  • Use the map to find apartments and other Vacation homes in the Town of Highlands neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Town of Highlands while they last

Look no further and take a look at our great range of rental properties in Town of Highlands!