Photo by Eugenio Ruiz

Search Vacation Homes in Peekskill

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Peekskill

3BR West Point Retreat-3min to Back Gate+ King Bed
9.4 out of 10, Exceptional, (3)
"Home was very peaceful and serene, My Boys really enjoyed the relaxing and laid back vibe this stay had to offer. My kids did mention it would be a summer vacation stay, because of the creek in the back. Overall is was clean and accommodating. Host did their best for all my accommodation. I would give them a 5- Star White Glove on this. Thanks, Hope to revisit! "
United States
Akail S.
$397 nightly
The price is $449
Nov 11 - Nov 12
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
$328 nightly
The price is $355
Nov 13 - Nov 14
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
9.0 out of 10, Wonderful, (10)
"We had a wonderful time staying at this charming and unique getaway! The accommodations were very comfortable. The property was beautiful and felt secluded without being isolated. The chapel itself is beautiful. The bathroom was overall nicer than we anticipated; just be mindful to put the camping shower out in the sun so the water warms up! Overall, highly recommend this experience. The hosts were also very responsive and kind."
United States
Avery D.
$228 nightly
The price is $258
Nov 6 - Nov 7
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (7)
"Celebrated my son’s HS graduation with my father-in-law along for the adventure, Joe’s townhouse is super convenient to Thayer Gate and eating establishments along Main St. Grill worked well and the beds made for sound slumber. For mixed company an extra half bath might be desired, but 3 guys who know each other well managed just fine. The basement washer & dryer are top of line."
United States
James W.
$311 nightly
The price is $352
Nov 17 - Nov 18
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (30)
"Very clean comfortable quiet place"
United States
Mauro C.
$370 nightly
The price is $423
Nov 6 - Nov 7
Total with taxes and fees
Contemporary Cozy Cottage
Fabulous 3bdrm Home w/parking!
8.0 out of 10, Very Good, (2)
"Great place. Close to West Point activity. Clean and new."
United States
Joanne V.
$297 nightly
The price is $327
Nov 17 - Nov 18
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
$470 nightly
The price is $477
Nov 17 - Nov 18
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Large,Cozy,Bright Apartment, Business Themed.
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
$585 nightly
The price is $691
Nov 6 - Nov 7
Total with taxes and fees
Large,Cozy,Bright Apartment, Business Themed.
Fun, Friends, and Family Lakefront Home w/Dock and Beach
10.0 out of 10, Exceptional, (12)
"Super convenient location :)"
United States
Sean M.
$672 nightly
The price is $728
Nov 9 - Nov 10
Total with taxes and fees
Fun, Friends, and Family Lakefront Home w/Dock and Beach
Marvelous 6-bedroom house with AC in Monroe
$3,093 nightly
The price is $3,499
Nov 6 - Nov 7
Total with taxes and fees
Marvelous 6-bedroom house with AC in Monroe
Luxury NY Home with Free Parking
4.0 star property
$558 nightly
The price is $638
Nov 7 - Nov 8
Total with taxes and fees
Luxury NY Home with Free Parking
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.6 out of 10, Exceptional, (45)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
United States
Lisa B.
$295 nightly
The price is $334
Nov 30 - Dec 1
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
West Point Villa - Jacuzzi Pool BBQ Games Pets
2.0 star property
$603 nightly
The price is $713
Nov 11 - Nov 12
Total with taxes and fees
West Point Villa - Jacuzzi Pool BBQ Games Pets
Chestnut on Willow Lake
9.4 out of 10, Exceptional, (3)
"We absolutely loved our stay in Chestnut—the home was spotless and comfortable, the property was terrific (the lake was perfect for swimming, boating, and fishing), and the owners/management were all very friendly and helpful. We definitely plan to return!"
United States
Lara S.
$608 nightly
The price is $693
Nov 6 - Nov 7
Total with taxes and fees
Chestnut on Willow Lake
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
10.0 out of 10, Exceptional, (26)
"Easy access and kitchen was well stocked. "
United States
Bob & Mary Anne H.
$453 nightly
The price is $512
Nov 12 - Nov 13
Total with taxes and fees
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
10.0 out of 10, Exceptional, (17)
"We had a great stay and had everything we needed!"
United States
Maueen Q.
$845 nightly
The price is $916
Nov 24 - Nov 25
Total with taxes and fees
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Amazing Home Near West Point, Shopping, Skiing and Legoland
10.0 out of 10, Exceptional, (13)
"It was a good retreat for a West Point activity. The home/yard could use a little updating. And my billing has an error that vrbo still hasn't corrected. But we were comfortable and neighborhood was nice. The host was helpful with lots of questions. I did miss the welcome book i have had in other Vrbo stays"
United States
Carole B.
$528 nightly
The price is $597
Nov 6 - Nov 7
Total with taxes and fees
Amazing Home Near West Point, Shopping, Skiing and Legoland
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
9.0 out of 10, Wonderful, (6)
"This is an incredibly unique property with some upsides. It is a cool old (1920's) Tudor style house that is well-suited for large groups. While it was fine for a couple of nights, any longer would have made the downsides (deferred maintenance, insufficient silverware, stained carpeting) less tolerable. There were also some communication issues with the property management company and the host during the stay. Specifically, we counted on there being a crib available, as it was specified in the...
United States
Marnie O.
$1,346 nightly
The price is $1,390
Dec 2 - Dec 3
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Red Cottage - Lakeside Property!
$648 nightly
The price is $738
Nov 10 - Nov 11
Total with taxes and fees
Red Cottage - Lakeside Property!
Hickory on Willow Lake
9.6 out of 10, Exceptional, (4)
"We stayed one night. Would loved to have stayed longer. Beautiful property. "
United States
Christine B.
$648 nightly
The price is $738
Nov 10 - Nov 11
Total with taxes and fees
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Peekskill Hotel Reviews

Find out more about Peekskill

Peekskill Vacation Homes information

Number of reviews
197
Accommodation
224 Vacation Homes
Lowest Price
$258
Highest Price
$3,499

Explore a world of travel with Expedia