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

Vacation Rentals in Town of Highlands

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Our top choices for Town of Highlands vacation rentals

A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

1. 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 ￥18,179
￥49,093 total
includes taxes & fees
Oct 18 - Oct 19
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Living area

2. 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 ￥18,092
￥34,450 total
includes taxes & fees
Oct 19 - Oct 20
Cozy 1-bedroom retreat minutes from West Point!
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

3. 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, (14 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 ￥19,921
￥64,107 total
includes taxes & fees
Oct 20 - Oct 21
House on the Babbling Brook- Quiet 2BR + King Bed!
A house with a view of a bridge and mountains.

4. 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 ￥31,300
￥52,099 total
includes taxes & fees
Oct 20 - Oct 21
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

5. 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 ￥24,354
￥48,782 total
includes taxes & fees
Oct 18 - Oct 19
Fabulous 3bdrm Home w/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 ￥24,354
￥45,035 total
includes taxes & fees
Oct 18 - Oct 19
Walk to WP Gate + Free Parking!
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

7. 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)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
The price is ￥21,984
￥71,243 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.

8. 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 ￥23,712
￥74,144 total
includes taxes & fees
Nov 2 - Nov 3
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A room with a wooden floor, a white door with a number, and a window with blinds.

9. 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 ￥27,043
￥53,218 total
includes taxes & fees
Oct 19 - Oct 20
Lovely 3BR Home with parking-Walk to WP Gate!
A hallway with a wooden door, a black table with a sign, and large green plants.

10. 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 ￥21,502
￥70,761 total
includes taxes & fees
Oct 21 - Oct 22
3BR Near West Point | Coffee Bar | Sleeps 6
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

11. 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 ￥32,537
￥55,395 total
includes taxes & fees
Nov 16 - Nov 17
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A modern kitchen with stainless steel appliances, a marble countertop, and a dining area with white chairs.

12. Hudson Valley/West Point Retreat w/ parking!

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is ￥30,279
￥58,260 total
includes taxes & fees
Oct 19 - Oct 20
Hudson Valley/West Point Retreat w/ parking!
The exterior of Highland Falls Library with a white facade, two wooden benches in front, and a sign above the entrance.

13. 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 ￥78,882
￥129,823 total
includes taxes & fees
Oct 18 - Oct 19
Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
A brick building with a sign reading 'Lobby' in front.

14. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.2 out of 10, Wonderful, (21 reviews)
"great place tostay"
United States
Anonymous traveler
The price is ￥13,701
￥15,842 total
includes taxes & fees
Nov 12 - Nov 13
2 Full Beds | Non-Smoking, Kitchen
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

15. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveler
The price is ￥12,456
￥14,090 total
includes taxes & fees
Oct 18 - Oct 19
1 King Bed | Non-Smoking, Kitchen, Shower
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 ￥21,341
￥46,854 total
includes taxes & fees
Oct 19 - Oct 20
Grant - A Tranquil One Bedroom Steps from River
A small blue house with two blue Adirondack chairs, a small table, and a potted plant.

17. Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2
Newburgh
9.6 out of 10, Exceptional, (41 reviews)
"This was a great place to stay with our cats for a night on our way to Vermont."
United States
George J.
The price is ￥18,182
￥30,070 total
includes taxes & fees
Oct 18 - Oct 19
Cabin in the heart of the Hudson Valley, Cabin 2
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

18. Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (36 reviews)
"Great place! Nicely decorated with attention to detail. My wife and I would stay again if we are back in the area."
United States
Tim G.
The price is ￥19,760
￥36,412 total
includes taxes & fees
Oct 19 - Oct 20
Cabin in the Heart of the Hudson Valley, Cabin 1
A brown backpack leaning against a wall, a pair of brown shoes on a black mat, and a view of a porch with a wicker chair and a white cushion.

19. Private River View Deck · Walk Downtown

Private River View Deck · Walk Downtown
Newburgh
10.0 out of 10, Exceptional, (1 review)
The price is ￥28,916
￥77,048 total
includes taxes & fees
Nov 3 - Nov 4
Private River View Deck · Walk Downtown
Interior

20. Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Warwick
10.0 out of 10, Exceptional, (53 reviews)
"Great location in the heart of Warwick, NY. Easy to walk around town and visit the local restaurants!"
United States
Francis
The price is ￥16,598
￥37,555 total
includes taxes & fees
Nov 1 - Nov 2
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
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 Town of Highlands Hotel Reviews

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent
"The place is like new, I highly recommend"
KURT 1-night trip
Posted 14 hours ago
Sleep Inn & Suites Monroe - Woodbury

Find out more about Town of Highlands

Vacation Apartments in Town of Highlands

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