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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Peekskill vacation 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.
$378 nightly
The price is $404
Sep 27 - Sep 28
Total with taxes and fees
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.
$367 nightly
The price is $420
Sep 30 - Oct 1
Total with taxes and fees
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.
$448 nightly
The price is $460
Oct 6 - Oct 7
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
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.
$640 nightly
The price is $706
Oct 7 - Oct 8
Total with taxes and fees
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A room with a wooden floor, a white door with a number, and a window with blinds.

5. 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.
$403 nightly
The price is $466
Oct 6 - Oct 7
Total with taxes and fees
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.

6. 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.
$430 nightly
The price is $484
Oct 6 - Oct 7
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
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
$351 nightly
The price is $415
Sep 27 - Sep 28
Total with taxes and fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
A wooden cabin with large windows, a wooden bench, and a view of the forest.

8. Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
$279 nightly
The price is $283
Sep 27 - Sep 28
Total with taxes and fees
Harriman Outdoor Center - Cranberry Cabin
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

9. 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.
$247 nightly
The price is $279
Sep 27 - Sep 28
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.

10. 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.
$387 nightly
The price is $420
Oct 5 - Oct 6
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A modern kitchen with grey cabinets, a central island, bar stools, and a stainless steel range hood.

11. 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.
$661 nightly
The price is $781
Sep 27 - Sep 28
Total with taxes and fees
Perfect and Spacious Hudson Valley Escape!
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

12. 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.
$605 nightly
The price is $715
Oct 22 - Oct 23
Total with taxes and fees
Bright Cornwall-On-Hudson Vacation Rental!
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.
$428 nightly
The price is $484
Sep 28 - Sep 29
Total with taxes and fees
Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

14. 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.
$969 nightly
The price is $997
Sep 28 - Sep 29
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
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.
$295 nightly
The price is $341
Sep 27 - Sep 28
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A hot tub with a view of a lake and houses in the background.

16. Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
10.0 out of 10, Exceptional, (41 reviews)
"We have stayed here a few times and the house is always perfect. Will stay here again in the future! "
United States
Lex S.
$493 nightly
The price is $558
Sep 29 - Sep 30
Total with taxes and fees
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

17. 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.
$886 nightly
The price is $1,047
Sep 29 - Sep 30
Total with taxes and fees
Luxury Hudson Valley Retreat near West Point, Storm King & Beacon
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.

18. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
$1,107 nightly
The price is $1,233
Sep 28 - Sep 29
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table
A room with a bed, a couch, a desk with a computer, and various wall decorations.

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

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
$261 nightly
The price is $283
Sep 28 - Sep 29
Total with taxes and fees
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
A room with two beds, white curtains, a ceiling light, and a window with a view.

20. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
2.0 out of 10, (1 review)
"This guy is a scammer, an hour before my checkin they finally sent me the "location" and claimed they needed more time to clean the property. Then at 5 pm and hour after they claimed their was a gas leak and I couldn't stay there. Only thing is the address they sent me wasn't real and I am convinced this listing is fake in and used to trick people into staying at their actual property in yonkers. DO NOT RENT FROM THEM!"
United States
Ethan G.
$477 nightly
The price is $546
Sep 27 - Sep 28
Total with taxes and fees
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"The property is a bit dated and its a bit odd to have to drive to the Inn to check in but it was mostly OK. Very rustic at the lodge and no staff onsite"
Dean 1-night trip
Posted 10 hours ago
Overlook Lodge at Bear Mountain

Find out more about Peekskill

Peekskill Vacation Homes information

Number of reviews
274
Accommodation
179 Vacation Homes
Lowest Price
$279
Highest Price
$1,233

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