A calm lake with a forested island in the distance, a picnic area, and a rocky shoreline.

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Our top choices for Peekskill vacation homes

1. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (43 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.
$350 nightly
The price is $400
Nov 11 - Nov 12
Total with taxes and fees
Contemporary Cozy Cottage

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

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
$239 nightly
The price is $264
Nov 11 - Nov 12
Total with taxes and fees
Perfect 2BR with Free Parking! Walk to West Point!

3. 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.
$378 nightly
The price is $430
Nov 11 - Nov 12
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed

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

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
$266 nightly
The price is $301
Nov 12 - Nov 13
Total with taxes and fees
Hudson Valley/West Point Retreat w/ parking!

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.
$263 nightly
The price is $290
Nov 11 - Nov 12
Total with taxes and fees
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.
$310 nightly
The price is $355
Dec 8 - Dec 9
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!

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

Spacious 4-bedroom house in northern Westchester with sweeping views
Montrose
$538 nightly
The price is $615
Nov 12 - Nov 13
Total with taxes and fees
Spacious 4-bedroom house in northern Westchester with sweeping views

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

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
8.0 out of 10, Very good, (3 reviews)
"This home was just as advertised and perfect for a girls weekend getaway. It was clean, cozy and a picture-perfect fall view. Would highly recommend."
United States
Karen W.
$605 nightly
The price is $667
Nov 16 - Nov 17
Total with taxes and fees
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

9. 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
$357 nightly
The price is $422
Nov 11 - Nov 12
Total with taxes and fees
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

10. 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.
$769 nightly
The price is $787
Nov 16 - Nov 17
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

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.
$575 nightly
The price is $679
Nov 22 - Nov 23
Total with taxes and fees
Bright Cornwall-On-Hudson Vacation Rental!

12. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
$947 nightly
The price is $1,054
Nov 16 - Nov 17
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table

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

NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed
New Windsor
$430 nightly
The price is $508
Nov 15 - Nov 16
Total with taxes and fees
NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed

14. 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.
$227 nightly
The price is $257
Nov 13 - Nov 14
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

15. 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.
$307 nightly
The price is $333
Nov 11 - Nov 12
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

16. 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.
$469 nightly
The price is $535
Nov 11 - Nov 12
Total with taxes and fees
Chestnut on Willow Lake

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.
$679 nightly
The price is $799
Nov 11 - Nov 12
Total with taxes and fees
Hudson View Hot Tub · Walk to Waterfront

18. Lakefront Paradise Pool + Paddle Boats Sleeps 12

Lakefront Paradise Pool + Paddle Boats Sleeps 12
Monroe
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful week long stay. The house is beautiful and right on the lake, with beautiful views and sunsetsWe were there for a West Point Graduation and was about a 30 minute drive to the school, even on the busy days of the parade and graduation dayThe house had plenty of room for our group and the host was easy to get ahold of. There are 4 official bedroom and 4 bathrooms and a basement and 2 office/den, 2 washer and dryers - one in the top floor and another in the basement which has...
United States
Courtney D.
$1,216 nightly
The price is $1,376
Nov 17 - Nov 18
Total with taxes and fees
Lakefront Paradise Pool + Paddle Boats Sleeps 12

19. Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair

Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair
Monroe
10.0 out of 10, Exceptional, (5 reviews)
"The combination of an antique, old-style house with a modernized interior featuring all the amenities you could dream of made for an enjoyable and cozy experience. The house is located right at the back of the lake in a quiet neighborhood and comes fully equipped with:- A spacious layout- High-speed Wi-Fi- Useful massage chair - Fun recreational areas- Lovely decorThis house will truly become a staple in the area."
United States
Moshe F.
$1,021 nightly
The price is $1,155
Nov 11 - Nov 12
Total with taxes and fees
Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair

20. Amazing Home Near West Point, Shopping, Skiing and Legoland

Amazing Home Near West Point, Shopping, Skiing and Legoland
Monroe
9.8 out of 10, Exceptional, (17 reviews)
"Very nice property in a nice neighborhood . Had all the amenities we needed and Ruth was super responsive. If we are in the area again, we will def stay at this location. "
United States
Kimberly R.
$597 nightly
The price is $705
Nov 11 - Nov 12
Total with taxes and fees
Amazing Home Near West Point, Shopping, Skiing and Legoland
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 Peekskill Hotel Reviews

Find out more about Peekskill

Peekskill Vacation Homes information

Number of reviews
134
Accommodation
183 Vacation Homes
Lowest Price
$257
Highest Price
$1,376

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