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Peekskill Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Peekskill holiday rentals

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

Holiday Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (5)
"A clean and convenient place to stay for visiting our cadet at West Point. Our hosts were very communicative and helpful. The home and parking situation was just as described. Nice quiet neighborhood, well maintained home. Hearing the babbling broom outside the living room window was very relaxing. Plan on staying here again!"
United States
Maria L.
The price is HK$863
HK$2,829 total
includes taxes & fees
20 Jan - 21 Jan 2026
House on the Babbling Brook- Quiet 2BR + King Bed!
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cabin in Carmel

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
3.0 star property
10.0 out of 10, Exceptional, (3)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
United States
Varuna S.
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Exterior detail
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Apartment in Highland Falls

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
The price is HK$699
HK$2,067 total
includes taxes & fees
19 Jan - 20 Jan 2026
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
1 bedroom, WiFi, bed sheets
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Apartment in Beacon

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
The price is HK$855
HK$1,870 total
includes taxes & fees
4 Jan - 5 Jan 2026
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Interior
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

Cottage in Putnam Valley

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
9.8 out of 10, Exceptional, (23)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Holiday Home in Highland Falls

Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is HK$1,088
HK$3,518 total
includes taxes & fees
14 Jan - 15 Jan 2026
Sleek Escape: Modern 3 BR- 4 Min from West Point !
1 bedroom, WiFi, bed sheets
Charming 1-bedroom apartment in Carmel with WiFi, AC

Apartment in Carmel Hamlet

Charming 1-bedroom apartment in Carmel with WiFi, AC
9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is HK$1,049
HK$2,164 total
includes taxes & fees
29 Dec - 30 Dec
Charming 1-bedroom apartment in Carmel with WiFi, AC
2 bedrooms, in-room safe, desk, iron/ironing board
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Apartment in CROTON HDSN

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is HK$873
HK$2,128 total
includes taxes & fees
4 Jan - 5 Jan 2026
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
Private kitchen
Elegant Hideaway with Free Parking

Apartment in White Plains

Elegant Hideaway with Free Parking
2.0 star property
The price is HK$777
HK$2,047 total
includes taxes & fees
26 Jan - 27 Jan 2026
Elegant Hideaway with Free Parking
TV, fireplace
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Holiday Home in Carmel Hamlet

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.
The price is HK$1,294
HK$2,750 total
includes taxes & fees
29 Dec - 30 Dec
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Smart TV
Grant - A Tranquil One Bedroom Steps from River

Apartment in Newburgh

Grant - A Tranquil One Bedroom Steps from River
9.6 out of 10, Exceptional, (41)
"Wonderful place! Beautifully decorated, high ceilings, yard, and easy access to the river and cafes. Perfect getaway from the city. Will stay again!"
United States
Emily G.
The price is HK$839
HK$2,013 total
includes taxes & fees
30 Dec - 31 Dec
Grant - A Tranquil One Bedroom Steps from River
Fridge, microwave, oven, stovetop
Local Artist Inspired | Walk to WestPoint + King Bed

Apartment in Highland Falls

Local Artist Inspired | Walk to WestPoint + King Bed
9.2 out of 10, Wonderful, (9)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is HK$909
HK$3,177 total
includes taxes & fees
14 Jan - 15 Jan 2026
Local Artist Inspired | Walk to WestPoint + King Bed
Property grounds
3BR West Point Retreat-3min to Back Gate+ King Bed

Holiday Home in Highland Falls

3BR West Point Retreat-3min to Back Gate+ King Bed
7.6 out of 10, Good, (5)
"Wonderful stay! The property is within walking distance of the little downtown area & had driveway parking. It was clean & plenty spacious. Property owners had great communication! This is a property with 2 units, but we were not bothered by any extra noise. "
United States
Waylon J.
3BR West Point Retreat-3min to Back Gate+ King Bed
Interior
Villa Verde B&B, bsm, Greenwood Lake NY

Aparthotel in Greenwood Lake

Villa Verde B&B, bsm, Greenwood Lake NY
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
The price is HK$1,220
HK$2,251 total
includes taxes & fees
1 Jan - 2 Jan 2026
Villa Verde B&B, bsm, Greenwood Lake NY
Interior
Charming Apartment in Quiet Neighborhood

Holiday Home in Tappan

Charming Apartment in Quiet Neighborhood
10.0 out of 10, Exceptional, (20)
"The location was perfect for our visit and the apartment was immaculately clean and well stocked."
United States
Claudia M.
The price is HK$762
HK$1,471 total
includes taxes & fees
14 Jan - 15 Jan 2026
Charming Apartment in Quiet Neighborhood
Fridge, microwave, oven, stovetop
Lux APT Your home away from home.

Apartment in Beacon

Lux APT Your home away from home.
10.0 out of 10, Exceptional, (2)
"Very clean and great place to stay. "
United States
Charlene D.
The price is HK$1,104
HK$2,119 total
includes taxes & fees
7 Jan - 8 Jan 2026
Lux APT Your home away from home.
Fridge, microwave, oven, stovetop
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Apartment in Highland Falls

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
10.0 out of 10, Exceptional, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is HK$1,273
HK$2,180 total
includes taxes & fees
7 Jan - 8 Jan 2026
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
1 bedroom, WiFi, bed sheets
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Apartment in Beacon

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is HK$855
HK$1,807 total
includes taxes & fees
6 Jan - 7 Jan 2026
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Dining
Luxury NYC Home with Free Parking for 12

Villa in White Plains

Luxury NYC Home with Free Parking for 12
4.0 star property
The price is HK$3,497
HK$5,286 total
includes taxes & fees
4 Jan - 5 Jan 2026
Luxury NYC Home with Free Parking for 12
Interior
Lovely 3BR Home with parking-Walk to WP Gate!

Holiday Home in Highland Falls

Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (7)
"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 HK$1,575
HK$2,919 total
includes taxes & fees
7 Jan - 8 Jan 2026
Lovely 3BR Home with parking-Walk to WP Gate!
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
"Jessica made my check in simple and quick! The room is always spotless! 🙏 The heat was great and the water was hot! Thanks Ardsley Acre’s motel! 🙏"
Sandra 1-night trip
Posted 10 hours ago
Ardsley Acres Hotel Westchester

Find out more about Peekskill

Search for holiday rentals in Peekskill on Expedia! You can easily find your home rentals, villas, holiday apartments in Peekskill using one of the methods below:

  • View our selection of featured holiday rentals in Peekskill
  • Use the map to find apartments and other holiday homes in the Peekskill neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Peekskill while they last

Look no further and take a look at our great range of rental properties in Peekskill!

Frequently asked questions

Can I find a holiday rental in Peekskill?

Yes, there are holiday rentals in Peekskill close to Lincoln Depot Museum, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the riverfront and mountain landscape in Peekskill. While you're here, grab a bite or have a drink at the restaurants.

What are some of the best holiday rentals that Peekskill has to offer?

Luxury NY Home with Free Parking: This holiday home rental outside Peekskill is in the city centre and offers free WiFi to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a full-sized fridge, a dishwasher and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Peekskill?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Peekskill stay.

What’s there to see and do in Peekskill?

Enjoy the outdoors at Blue Mountain Reservation and Charles Point Pier Park, or simply take in cultural attractions like Paramount Hudson Valley Theater and Peekskill Museum. Other places in town to visit include Hudson Valley Center for Contemporary Art and Dramatic Hall.

What’s a holiday rental in Peekskill like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Peekskill. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family getaway.