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

Holiday Homes in Peekskill

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Peekskill holiday homes

A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

1. 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, (12 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is AU$565
includes taxes & fees
29 Sept - 30 Sept
House on the Babbling Brook- Quiet 2BR + King Bed!
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

2. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (40 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is AU$588
includes taxes & fees
30 Sept - 1 Oct
Contemporary Cozy Cottage
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

3. 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.
The price is AU$632
includes taxes & fees
29 Sept - 30 Sept
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A room with a wooden floor, a white door with a number, and a window with blinds.

4. 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.
The price is AU$618
includes taxes & fees
30 Sept - 1 Oct
Lovely 3BR Home with parking-Walk to WP Gate!
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

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.
The price is AU$641
includes taxes & fees
30 Sept - 1 Oct
Fabulous 3bdrm Home w/parking!
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

6. 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.
The price is AU$1,048
includes taxes & fees
1 Oct - 2 Oct
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A deck with Adirondack chairs, a fire pit, and a grill.

7. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (15 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is AU$629
includes taxes & fees
6 Oct - 7 Oct
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

8. NYC-Area Escape Near River, Trails & MTA!

NYC-Area Escape Near River, Trails & MTA!
Ossining
8.2 out of 10, Very good, (19 reviews)
"A family trip with teens and tweens- a perfect space! Clean, hist was friendly, the house was stocked with all we'd need! A great getaway for any family NYC trip!"
United States
Justeen P.
The price is AU$1,192
includes taxes & fees
21 Oct - 22 Oct
NYC-Area Escape Near River, Trails & MTA!
A wooden cabin with large windows, a wooden bench, and a view of the forest.

9. Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
The price is AU$398
includes taxes & fees
29 Sept - 30 Sept
Harriman Outdoor Center - Cranberry Cabin
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

10. 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.
The price is AU$398
includes taxes & fees
29 Sept - 30 Sept
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A room with a bed, a couch, a desk with a computer, and various wall decorations.

11. Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is AU$405
includes taxes & fees
29 Sept - 30 Sept
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
A modern kitchen with grey cabinets, a central island, bar stools, and a stainless steel range hood.

12. Perfect and Spacious Hudson Valley Escape!

Perfect and Spacious Hudson Valley Escape!
Cornwall
8.0 out of 10, Very good, (3 reviews)
"Great host, very responsive and accommodating. The house was very clean and comfortable."
United States
Joseph S.
The price is AU$1,143
includes taxes & fees
29 Sept - 30 Sept
Perfect and Spacious Hudson Valley Escape!
A modern kitchen with a central island, bar stools, a round table, and a window with a view.

13. Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
Greenwood Lake
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and really cute place. "
United States
Katie C.
The price is AU$679
includes taxes & fees
29 Sept - 30 Sept
Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

14. Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (34 reviews)
"We had a girlfriend get away long weekend. This was a great house and really convenient location. Two really good restaurants were within walking distance just around the corner. I would highly recommend staying here!"
United States
Dawn H.
The price is AU$986
includes taxes & fees
22 Oct - 23 Oct
Bright Cornwall-On-Hudson Vacation Rental!
An outdoor patio area with a covered seating area, a pool, and potted plants.

15. 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, (78 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
The price is AU$487
includes taxes & fees
30 Sept - 1 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

16. 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
9.8 out of 10, Exceptional, (20 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is AU$574
includes taxes & fees
5 Oct - 6 Oct
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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.

17. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is AU$1,756
includes taxes & fees
29 Sept - 30 Sept
Summer Pool Oasis Custom Bar Arcade Pool Table
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

18. 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.
The price is AU$1,419
includes taxes & fees
5 Oct - 6 Oct
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

19. 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.
The price is AU$1,464
includes taxes & fees
29 Sept - 30 Sept
Luxury Hudson Valley Retreat near West Point, Storm King & Beacon
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

Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester

10/10 Excellent
"Excellent service always go back"
Jose 1-night trip
Posted 3 hours ago
Ardsley Acres Hotel Westchester

Find out more about Peekskill

Peekskill Holiday Homes information

Number of reviews
251
Accommodation
177 Holiday Homes
Lowest Price
AU$398
Highest Price
AU$1,756