Search Vacation Homes in Lake Peekskill

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Outdoor dining

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (302)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
The price is HK$3,525
HK$4,729 total
includes taxes & fees
24 Aug - 25 Aug
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
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, (27)
"Perfect for small family stay over for a wedding ! "
The price is HK$2,033
HK$2,602 total
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, (86)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Terrace/patio

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

9.6 out of 10, Exceptional, (9)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Smart TV, fireplace

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.0 out of 10, Wonderful, (37)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.
Microwave, oven, stovetop, dishwasher

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.
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!
The Woodbury Cottage
Property grounds

The Woodbury Cottage

8.8 out of 10, Excellent, (23)
"Really enjoyed our stay at this comfy cottage. Easily slept a family of 3 with plenty of room to lounge around. It's an older cottage, but the owner has added a lot of neat touches that make this a nice place to stay in this area."
The Woodbury Cottage
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!
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!
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
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Fridge, microwave, oven, stovetop

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

10.0 out of 10, Exceptional, (54)
"Awesome property. Will visit again. "
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
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!
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
Historic Hideaway with Lake Access!
Property grounds

Historic Hideaway with Lake Access!

9.8 out of 10, Exceptional, (17)
"The home was clean and the area is beautiful! It was a wonderful experience staying in a historic home and the owners were fantastic!"
Historic Hideaway with Lake Access!
Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town

10.0 out of 10, Exceptional, (4)
"Home was beatiful and spacious with large backyard. Convenient to hiking and sightseeing!"
Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town
Lakeside Haven - Ultimate Relaxation Spot
Interior

Lakeside Haven - Ultimate Relaxation Spot

Lakeside Haven - Ultimate Relaxation Spot
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.
Harriman Outdoor Center - White Oak Cabin
Property grounds

Harriman Outdoor Center - White Oak Cabin

The price is HK$1,672
HK$1,943 total
includes taxes & fees
13 Aug - 14 Aug
Harriman Outdoor Center - White Oak Cabin
Private lake escape
Outdoor pool

Private lake escape

Private lake escape
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Lake Peekskill Hotel Reviews

Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel

10/10 Excellent
"Clean, people were professional and polite. Lovey "
JAMES 4-night trip
Posted 20 hours ago
Sheraton Tarrytown Hotel