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

Holiday Rentals in Town of Highlands

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Our top choices for Town of Highlands holiday 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 €357
includes taxes & fees
1 Oct - 2 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
A house with a view of a bridge and mountains.

2. 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, (146 reviews)
"We had a great stay!!"
United States
Jasmine
The price is €301
includes taxes & fees
6 Oct - 7 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.4 out of 10, Exceptional, (24 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is €280
includes taxes & fees
1 Oct - 2 Oct
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

4. 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 €243
includes taxes & fees
1 Oct - 2 Oct
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
The exterior of Highland Falls Library with a white facade, two wooden benches in front, and a sign above the entrance.

5. 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 €737
includes taxes & fees
11 Oct - 12 Oct
Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

6. 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 €415
includes taxes & fees
6 Oct - 7 Oct
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.

7. 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 €418
includes taxes & fees
6 Oct - 7 Oct
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.

8. 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 €414
includes taxes & fees
28 Oct - 29 Oct
Fabulous 3bdrm Home w/parking!
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 €295
includes taxes & fees
1 Oct - 2 Oct
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, (1 review)
"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 €390
includes taxes & fees
6 Oct - 7 Oct
3BR Near West Point | Coffee Bar | Sleeps 6
Living area

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
9.0 out of 10, Wonderful, (4 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 €224
includes taxes & fees
28 Oct - 29 Oct
Cozy 1-bedroom retreat minutes from West Point!
A wooden coffee table with two decorative planters in a living room.

12. 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 €380
includes taxes & fees
28 Oct - 29 Oct
Walk to WP Gate + Free Parking!
A deck with Adirondack chairs, a fire pit, and a grill.

13. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (15 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is €388
includes taxes & fees
6 Oct - 7 Oct
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

14. Bright Cornwall-on-hudson Vacation Rental!

Bright Cornwall-on-hudson Vacation Rental!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
Bright Cornwall-on-hudson Vacation Rental!
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

15. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (40 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 €370
includes taxes & fees
4 Oct - 5 Oct
Contemporary Cozy Cottage
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 €268
includes taxes & fees
5 Oct - 6 Oct
Grant - A Tranquil One Bedroom Steps from River
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

17. Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (34 reviews)
"We had a girlfriend get away long weekend. This was a great house and really convenient location. Two really good restaurants were within walking distance just around the corner. I would highly recommend staying here!"
United States
Dawn H.
The price is €618
includes taxes & fees
22 Oct - 23 Oct
Bright Cornwall-On-Hudson Vacation Rental!
A stone staircase leading to a house with a stone wall and a metal gate.

18. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (24 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is €378
includes taxes & fees
21 Oct - 22 Oct
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A neatly made bed with a black and white duvet, a wooden headboard, and a bedside table with a lamp. There are three framed artworks on the wall above the bed.

19. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (3 reviews)
"Great stay!"
United States
Ann S.
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A modern kitchen with dark cabinets, a stainless steel stove, and a wooden countertop.

20. Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
10.0 out of 10, Exceptional, (1 review)
The price is €257
includes taxes & fees
4 Oct - 5 Oct
Carriage House Apartment Goshen 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.
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Top Town of Highlands Hotel Reviews

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent
"Clean room great breakfast"
Stacie 1-night trip
Posted 8 hours ago
Hyatt Place Poughkeepsie / Hudson Valley

Find out more about Town of Highlands

Holiday Homes in Town of Highlands

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