Peekskill Vacation Homes

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

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Our top choices for Peekskill holiday homes

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

1. Contemporary Cozy Cottage

Lake Peekskill

Aj L.

HK$3,205 total

includes taxes & fees

18 Oct - 19 Oct

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

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

Highland Falls

Leann M.

HK$3,173 total

includes taxes & fees

20 Oct - 21 Oct

A house with a white front door, a small porch with a white railing, and a window with a green curtain.

3. Fabulous 3bdrm Home w/parking!

Highland Falls

Beth M.

HK$2,392 total

includes taxes & fees

19 Oct - 20 Oct

A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

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

Highland Falls

James U.

HK$3,681 total

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with stainless steel appliances, a marble countertop, and a dining area with white chairs.

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

Highland Falls

HK$2,892 total

includes taxes & fees

19 Oct - 20 Oct

A room with a wooden floor, a white door with a number, and a window with blinds.

6. Lovely 3BR Home with parking-Walk to WP Gate!

Highland Falls

Briana T.

HK$2,641 total

includes taxes & fees

21 Oct - 22 Oct

A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

7. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lake Peekskill

Angel R.

HK$5,639 total

includes taxes & fees

21 Oct - 22 Oct

A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

8. Snow Days & City Escapes: Spacious Ossining Home

Ossining

Justeen P.

HK$6,196 total

includes taxes & fees

21 Oct - 22 Oct

A deck with Adirondack chairs, a fire pit, and a grill.

9. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

Cornwall

Elisabeth

HK$3,421 total

includes taxes & fees

2 Nov - 3 Nov

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

Cornwall

Jeff M.

HK$7,573 total

includes taxes & fees

27 Oct - 28 Oct

A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

11. Bright Cornwall-On-Hudson Vacation Rental!

Cornwall-On-Hudson

Dawn H.

HK$5,608 total

includes taxes & fees

22 Oct - 23 Oct

A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

12. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction

Peter W.

HK$2,193 total

includes taxes & fees

18 Oct - 19 Oct

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.

13. Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

HK$8,201 total

includes taxes & fees

3 Nov - 4 Nov

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!

Ossining

natalie l.

HK$7,600 total

includes taxes & fees

9 Nov - 10 Nov

A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

15. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Carmel Hamlet

Robert T.

HK$2,925 total

includes taxes & fees

3 Nov - 4 Nov

A modern living room with a stone fireplace, large windows, and a cozy seating area.

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

Monroe

"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."

Daniel S.

HK$11,592 total

includes taxes & fees

29 Oct - 30 Oct

A kitchen with white cabinets, stainless steel appliances, a microwave, oven, and a refrigerator.

17. Amazing Home Near West Point, Shopping, Skiing and Legoland

Monroe

Kimberly R.

HK$5,626 total

includes taxes & fees

29 Oct - 30 Oct

A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

18. Chestnut on Willow Lake

Fishkill

Quintina R.

HK$4,416 total

includes taxes & fees

11 Nov - 12 Nov

A lakeside seating area with Adirondack chairs arranged around a central fire pit.

19. Red Cottage - Lakeside Property!

Fishkill

HK$3,219 total

includes taxes & fees

11 Nov - 12 Nov

An outdoor patio area with a covered seating area, a pool, and potted plants.

20. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Fishkill

Roger S.

HK$2,840 total

includes taxes & fees

28 Oct - 29 Oct

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Top Peekskill Hotel Reviews

Overlook Lodge at Bear Mountain

10/10 Excellent

"Bear Mountain Inn is a unique and beautiful retreat in the heart of the Hudson Valley. We go for the scenery, hiking, and watching the marine and rail traffic along the Hudson River. Staff is always helpful. We booked 2 nights but could only. stay 1 due to a family emergency and the staff worked with Expedia to refund the 2nd night. Will definitely return as we love the atmosphere. Stayed in 1 of the stone cottages in the woods above the lake. Basic room with a shared common area and outdoor porch/deck. Room had a small refrigerator and TV with local channels. Clean and quiet and what you'd expect in a state or national park setting. Great 1.5 mile paved walking trail below the cottage that circles the picturesque lake on the property grounds. Nice way to start the day."

West Gate Inn Nyack

8/10 Good

"Excellent hot breakfast. I loved the fact that even being a buffet it was served by the personnel which talks about caring and healthy consideration. Room was clean, comfortable big and enough for the four of us. Parking was easy and just at the room's door. Staff was nice and helpful. The caveat was the wifi not working properly for us, probably signal not good enough since we were at the further distance from the lobby."

Ardsley Acres Hotel Westchester

8/10 Good

"They're doing construction around the office we didn't see any amenities and the main road noise is a disappointment, lots of it, fast and all night. but otherwise the room was clean and otherwise quiet as far as guests are concerned. Not too sure about the excellent rating but I guess it's all by comparison. We would stay here again for the right price. Really no complaints other than those listed."

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