A lake surrounded by hills with autumn foliage.

Holiday Homes in Highland Falls

  • 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

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Highland Falls holiday homes

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, (16 reviews)
"Host was available and communicated very well. The house was very clean too."
United States
Erika
The price is NZ$688
includes taxes & fees
29 Oct - 30 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

2. 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 NZ$532
includes taxes & fees
29 Oct - 30 Oct
Fabulous 3bdrm Home w/parking!
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

3. 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 NZ$852
includes taxes & fees
2 Nov - 3 Nov
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A blue house with a white porch, a welcome sign, and a mailbox.

4. 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 NZ$813
includes taxes & fees
2 Nov - 3 Nov
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.

5. 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 NZ$703
includes taxes & fees
17 Nov - 18 Nov
Lovely 3BR Home with parking-Walk to WP Gate!
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is NZ$913
includes taxes & fees
17 Nov - 18 Nov
Hudson Valley/West Point Retreat w/ parking!
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

7. 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 NZ$717
includes taxes & fees
2 Nov - 3 Nov
Contemporary Cozy Cottage
A deck with Adirondack chairs, a fire pit, and a grill.

8. 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, (16 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is NZ$746
includes taxes & fees
1 Nov - 2 Nov
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

9. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay at the lake house. The home is beautiful inside and out, and there is every amenity you could think of, from cooking and cleaning supplies to extra towels and blankets. The view of the lake is stunning and we enjoyed the peace and quiet of the little community. Linh is an excellent host and helped answer all of our questions. We will definitely be back!"
United States
Angel R.
The price is NZ$1,153
includes taxes & fees
4 Nov - 5 Nov
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

10. Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (35 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 NZ$1,227
includes taxes & fees
22 Nov - 23 Nov
Bright Cornwall-On-Hudson Vacation Rental!
Room

11. Luxury Hudson Valley Retreat near West Point, Storm King & Beacon

Luxury Hudson Valley Retreat near West Point, Storm King & Beacon
Cornwall
9.0 out of 10, Wonderful, (2 reviews)
"Great House, less than 15 mins to front gate at West Point, convenient location for visiting and enjoying activities at West Point, e.g. football games, cadet events for family members, etc. Hope to be able to stay there again on another visit to the "Rockbound Highland Home"!!! "
United States
Jeff M.
The price is NZ$1,848
includes taxes & fees
29 Oct - 30 Oct
Luxury Hudson Valley Retreat near West Point, Storm King & Beacon
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

12. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is NZ$488
includes taxes & fees
29 Oct - 30 Oct
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A bed in a tent-like room with a view of trees through a window.

13. Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.
Newburgh
9.0 out of 10, Wonderful, (17 reviews)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is NZ$969
includes taxes & fees
9 Nov - 10 Nov
Large,Cozy,Bright Apartment, Business Themed.
A room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

14. Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.6 out of 10, Excellent, (20 reviews)
"I absolutely loved my stay. A beautiful place with Victorian inspired, a big comfy bed, a really nice cozy reading nook with stone glass windows, and had an enjoyable stay!! Very easy check-in and check-out process. Great air conditioning during a heat wave!!"
United States
Daisy
The price is NZ$282
includes taxes & fees
2 Nov - 3 Nov
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
An outdoor patio area with a covered seating area, a pool, and potted plants.

15. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (81 reviews)
"The property was as advertised and met our needs for our trip."
United States
Sara
The price is NZ$630
includes taxes & fees
3 Nov - 4 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A room with a bay window overlooking a lake and autumn foliage, featuring two green armchairs, a small table, and a potted plant.

16. Hudson View Hot Tub · Walk to Waterfront

Hudson View Hot Tub · Walk to Waterfront
Newburgh
10.0 out of 10, Exceptional, (1 review)
"The home has recently been renovated and it is very well presented with luxury furnishings and an excellently stocked kitchen. Views are amazing over the Hudson towards Beacon."
United States
Rachel M.
The price is NZ$1,439
includes taxes & fees
29 Oct - 30 Oct
Hudson View Hot Tub · Walk to Waterfront
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

17. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed a relaxing weekend before R-day at West Point and it was perfect! A beautiful property and we hope to be back another time!"
United States
Quintina R.
The price is NZ$962
includes taxes & fees
23 Nov - 24 Nov
Chestnut on Willow Lake
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

18. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is NZ$613
includes taxes & fees
3 Nov - 4 Nov
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A lakeside seating area with Adirondack chairs arranged around a central fire pit.

19. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is NZ$736
includes taxes & fees
11 Nov - 12 Nov
Red Cottage - Lakeside Property!
A hot tub in a lush garden with a stone wall and outdoor furniture.

20. Country House w/Hot Tub, Deck, Grill & Fire Pit

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
9.8 out of 10, Exceptional, (69 reviews)
"We had a nice weekend at the Country House. I would recommend this property to friends and family. "
United States
Mike T.
The price is NZ$940
includes taxes & fees
1 Nov - 2 Nov
Country House w/Hot Tub, Deck, Grill & Fire Pit
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 Highland Falls Hotel Reviews

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

8/10 Good
"Located close to the highway but surprisingly quiet. We stayed 3 nights. Same breakfast offerings each day (sausage patties and egg patties as well as biscuits and gravy and waffles and the other usual stuff). Small indoor pool but no hot tub. Very fast elevators"
Mary 3-night trip
Posted 2 hours ago
Comfort Suites Fishkill near Interstate 84

Find out more about Highland Falls

Highland Falls Holiday Homes information

Number of reviews
349
Accommodation
227 Holiday Homes
Lowest Price
NZ$282
Highest Price
NZ$1,848