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

Search Vacation Homes in Peekskill

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Peekskill vacation homes

A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

1. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (41 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
$370 nightly
The price is $423
Oct 25 - Oct 26
Total with taxes and fees
Contemporary Cozy Cottage
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

2. 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.
$362 nightly
The price is $405
Nov 17 - Nov 18
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

3. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (14 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
$381 nightly
The price is $408
Oct 27 - Oct 28
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

4. 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.
$597 nightly
The price is $658
Nov 1 - Nov 2
Total with taxes and fees
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

5. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
$486 nightly
The price is $499
Nov 1 - Nov 2
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A blue house with a white porch, a welcome sign, and a mailbox.

6. 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.
$448 nightly
The price is $512
Oct 26 - Oct 27
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed
A room with a wooden floor, a white door with a number, and a window with blinds.

7. 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.
$343 nightly
The price is $394
Nov 17 - Nov 18
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
A modern kitchen with stainless steel appliances, a marble countertop, and a dining area with white chairs.

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

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
$364 nightly
The price is $419
Oct 26 - Oct 27
Total with taxes and fees
Hudson Valley/West Point Retreat w/ parking!
A deck with Adirondack chairs, a fire pit, and a grill.

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
$369 nightly
The price is $436
Nov 1 - Nov 2
Total with taxes and fees
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

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)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
$831 nightly
The price is $852
Nov 4 - Nov 5
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

11. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
$977 nightly
The price is $1,089
Nov 3 - Nov 4
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table
Room

12. Luxury Hudson Valley Retreat near West Point, Storm King & Beacon

Luxury Hudson Valley Retreat near West Point, Storm King & Beacon
Cornwall
9.0 out of 10, Wonderful, (2 reviews)
"Great House, less than 15 mins to front gate at West Point, convenient location for visiting and enjoying activities at West Point, e.g. football games, cadet events for family members, etc. Hope to be able to stay there again on another visit to the "Rockbound Highland Home"!!! "
United States
Jeff M.
$817 nightly
The price is $965
Oct 27 - Oct 28
Total with taxes and fees
Luxury Hudson Valley Retreat near West Point, Storm King & Beacon
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

13. 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.
$249 nightly
The price is $282
Oct 25 - Oct 26
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

14. 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.
$324 nightly
The price is $351
Nov 3 - Nov 4
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A modern living room with a stone fireplace, large windows, and a cozy seating area.

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

Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair
Monroe
10.0 out of 10, Exceptional, (5 reviews)
"Great house for a big group! We were in town for a wedding and had plenty of space for 10 adults. Everything clean and a nice view from the deck. Kitchen stocked with keurig pods which was very appreciated. Big driveway which was nice.Only thing to note is there’s no communal bathrooms upstairs, 3 of the rooms have en suite bath but the 4th room needs to walk downstairs. Only relevant if you are filling all 6 king/queen rooms."
United States
Daniel S.
$1,029 nightly
The price is $1,164
Nov 1 - Nov 2
Total with taxes and fees
Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair
A kitchen with white cabinets, stainless steel appliances, a microwave, oven, and a refrigerator.

16. 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.
$629 nightly
The price is $743
Oct 27 - Oct 28
Total with taxes and fees
Amazing Home Near West Point, Shopping, Skiing and Legoland
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

17. 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.
$494 nightly
The price is $564
Nov 1 - Nov 2
Total with taxes and fees
Hickory on Willow Lake
An outdoor patio area with a covered seating area, a pool, and potted plants.

18. 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
$313 nightly
The price is $362
Nov 11 - Nov 12
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A lakeside seating area with Adirondack chairs arranged around a central fire pit.

19. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
$367 nightly
The price is $418
Nov 11 - Nov 12
Total with taxes and fees
Red Cottage - Lakeside Property!
A modern kitchen with white cabinets, a marble countertop, and a built-in oven.

20. 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.
$740 nightly
The price is $869
Oct 25 - Oct 26
Total with taxes and fees
Hudson View Hot Tub · Walk to Waterfront
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

Tappan Zee Hotel

Tappan Zee Hotel

10/10 Excellent
"Decent place for 1 night"
Kristal 1-night trip
Posted 15 hours ago
Tappan Zee Hotel

Find out more about Peekskill

Peekskill Vacation Homes information

Number of reviews
238
Accommodation
183 Vacation Homes
Lowest Price
$282
Highest Price
$1,164

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