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Holiday Homes in Peekskill

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Peekskill

Our top choices for Peekskill holiday homes

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

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

9.8 out of 10, Exceptional, (29)
"Great place for a quiet stay"
The price is AU$519
includes taxes & fees
31 Aug - 1 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (87)
"It was very nice "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
⭐️❤️Historic Town ⭐️ Bridge View ⭐️ Walk Everywhere ⭐️ Quick Train to NYC
Pool

⭐️❤️Historic Town ⭐️ Bridge View ⭐️ Walk Everywhere ⭐️ Quick Train to NYC

4.0 star property
10.0 out of 10, Exceptional, (7)
"This place was perfect for our family members - 7 adults. Everyone had their own bed and there were plenty of pillows and towels for all. It was quite clean and decorated nicely. The kitchen was well stocked with anything we might need and more. Thank you to the excellent hosts!"
⭐️❤️Historic Town ⭐️ Bridge View ⭐️ Walk Everywhere ⭐️ Quick Train to NYC
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Outdoor spa tub

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (17)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is AU$910
includes taxes & fees
15 Sept - 16 Sept
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Bright Cornwall-On-Hudson Vacation Rental!
Fridge, microwave, stovetop, dishwasher

Bright Cornwall-On-Hudson Vacation Rental!

10.0 out of 10, Exceptional, (22)
"Property was perfect for our needs."
Bright Cornwall-On-Hudson Vacation Rental!
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Smart TV, fireplace

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2.0 star property
9.4 out of 10, Exceptional, (8)
"This property is great, our stay here was just amazing from start to finish. Communication with the host was great, we left some items there and the host was super accommodating. Would recommend this property very highly."
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Modern NY Home w/ Views By Hudson Valley Hiking!
TV, fireplace, books, video library

Modern NY Home w/ Views By Hudson Valley Hiking!

9.8 out of 10, Exceptional, (25)
"Lovely home and great proximity to Taconic Parkway for all points north and south. Owner very accomodating"
Modern NY Home w/ Views By Hudson Valley Hiking!
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Fridge, microwave, stovetop, dishwasher

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

10.0 out of 10, Exceptional, (36)
"Perfect for our family’s visit to West Point. Great location "
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Charming Highland Falls Home < 2 Mi to West Point!
Exterior

Charming Highland Falls Home < 2 Mi to West Point!

10.0 out of 10, Exceptional, (9)
"Wonderful front porch "
Charming Highland Falls Home < 2 Mi to West Point!
Large,Cozy,Bright Apartment, Business Themed.
Interior

Large,Cozy,Bright Apartment, Business Themed.

9.0 out of 10, Wonderful, (13)
"Very cozy stay with responsive host"
The price is AU$1,033
includes taxes & fees
23 Aug - 24 Aug
Large,Cozy,Bright Apartment, Business Themed.
Cozy Cabin with Sauna & Firepit!
Terrace/patio

Cozy Cabin with Sauna & Firepit!

9.2 out of 10, Wonderful, (34)
"We had a peaceful stay here while we were in town for a few days.The cabin was very cute, clean, and the neighborhood/ neighbors were very quiet. The steps into the bathroom and bedroom were illuminated and the upstairs loft was a cool getaway for our teenager.Recommend taking a bigger vehicle that can take a rough gravel road."
Cozy Cabin with Sauna & Firepit!
Serene Hudson Valley Escape w/ Pool & Grill
Fridge, microwave, stovetop, dishwasher

Serene Hudson Valley Escape w/ Pool & Grill

10.0 out of 10, Exceptional, (3)
"Beautiful home and great host!"
Serene Hudson Valley Escape w/ Pool & Grill
4 Mi to Hudson River: Cozy Newburgh Home!
Fridge, oven, stovetop, dishwasher

4 Mi to Hudson River: Cozy Newburgh Home!

9.0 out of 10, Wonderful, (4)
"Great place to stay in Newburgh- house was equipped with everything we needed for a very wonderful 5 days!"
4 Mi to Hudson River: Cozy Newburgh Home!
Home: 2 Mi to Thayer Gate at U.S. Military Academy
Fridge, microwave, stovetop, dishwasher

Home: 2 Mi to Thayer Gate at U.S. Military Academy

10.0 out of 10, Exceptional, (2)
"Your home was amazing! My family and I enjoyed every minute! "
Home: 2 Mi to Thayer Gate at U.S. Military Academy
Charming 3-bedroom house.
Property grounds

Charming 3-bedroom house.

2.0 star property
10.0 out of 10, Exceptional, (10)
"The property was very clean and nicely furnished. A nice quiet spot."
Charming 3-bedroom house.
Harriman Outdoor Center - White Oak Cabin
Property grounds

Harriman Outdoor Center - White Oak Cabin

The price is AU$382
includes taxes & fees
7 Sept - 8 Sept
Harriman Outdoor Center - White Oak Cabin
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY
Smart TV, fireplace

Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY

10.0 out of 10, Exceptional, (21)
"Despite the weather we had a great time. The house is very comfortable, well a pointed, nicely updated and was spotless when we arrived. Location is good too!"
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY
Lovely 3BR Home with parking-Walk to WP Gate!
Interior

Lovely 3BR Home with parking-Walk to WP Gate!

10.0 out of 10, Exceptional, (4)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
The price is AU$572
includes taxes & fees
27 Aug - 28 Aug
Lovely 3BR Home with parking-Walk to WP Gate!
Updated Home w/ Patio Half Mile to West Point
Property grounds

Updated Home w/ Patio Half Mile to West Point

10.0 out of 10, Exceptional, (28)
"We were visiting West Point Academy and wanted a place to stay for our family of five. Perfect location and just what we needed for a couple of nights. Would stay again if we are back in the area!"
Updated Home w/ Patio Half Mile to West Point
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.
Interior

Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

10.0 out of 10, Exceptional, (39)
"Everything was good. Heather was very attentive."
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.
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

Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

10/10 Excellent
"This location is great! The room was huge! Every part of the property was clean and well-managed. The staff is warm and inviting. The breakfast was a nice bonus before the ride home."
John 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG