Holiday Homes in Lake Peekskill

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Our top choices for Lake Peekskill holiday homes

1. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (42 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
United States
Heather M.
The price is NZ$700
includes taxes & fees
8 Nov - 9 Nov
Contemporary Cozy Cottage

2. 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$1,087
includes taxes & fees
17 Nov - 18 Nov
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

3. Perfect 2BR with Free Parking! Walk to West Point!

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
The price is NZ$467
includes taxes & fees
9 Nov - 10 Nov
Perfect 2BR with Free Parking! Walk to West Point!

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$815
includes taxes & fees
10 Nov - 11 Nov
3BR West Point Retreat-3min to Back Gate+ King Bed

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 NZ$514
includes taxes & fees
8 Nov - 9 Nov
Fabulous 3bdrm Home w/parking!

6. 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$527
includes taxes & fees
8 Nov - 9 Nov
Lovely 3BR Home with parking-Walk to WP Gate!

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

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is NZ$592
includes taxes & fees
9 Nov - 10 Nov
Hudson Valley/West Point Retreat w/ parking!

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$758
includes taxes & fees
9 Nov - 10 Nov
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

9. 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$473
includes taxes & fees
8 Nov - 9 Nov
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

10. Spacious 4-bedroom house in northern Westchester with sweeping views

Spacious 4-bedroom house in northern Westchester with sweeping views
Montrose
The price is NZ$1,082
includes taxes & fees
9 Nov - 10 Nov
Spacious 4-bedroom house in northern Westchester with sweeping views

11. Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (35 reviews)
"Very comfortable house and great location."
United States
Betty B.
The price is NZ$1,151
includes taxes & fees
22 Nov - 23 Nov
Bright Cornwall-On-Hudson Vacation Rental!

12. NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed

NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed
New Windsor
The price is NZ$870
includes taxes & fees
16 Nov - 17 Nov
NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed

13. 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$593
includes taxes & fees
9 Nov - 10 Nov
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

14. 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$953
includes taxes & fees
11 Nov - 12 Nov
Chestnut on Willow Lake

15. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is NZ$715
includes taxes & fees
16 Nov - 17 Nov
Red Cottage - Lakeside Property!

16. 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$558
includes taxes & fees
15 Nov - 16 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

17. 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$1,397
includes taxes & fees
8 Nov - 9 Nov
Hudson View Hot Tub · Walk to Waterfront

18. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"It's an elegant older house with lots of room for company. Family friendly. The pool was great. My family enjoyed it."
United States
Karen O.
The price is NZ$1,373
includes taxes & fees
9 Nov - 10 Nov
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

19. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is NZ$1,815
includes taxes & fees
9 Nov - 10 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table

20. Hickory on Willow Lake

Hickory on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean, quiet and great location. Beautiful property."
United States
Sheila B.
The price is NZ$953
includes taxes & fees
9 Nov - 10 Nov
Hickory on Willow Lake
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.

Learn more about Lake Peekskill

Nestled in the Hudson Valley, this small lake community offers peaceful shoreline walks and easy access to Canopus Beach for summer swimming. Catch a show at nearby Paramount Hudson Valley Theatre or spend a day bargain-hunting at Woodbury Common Premium Outlets just a short drive away.

A calm lake surrounded by dense evergreen trees and a few deciduous trees with autumn leaves.

Top reviews in Lake Peekskill