Lake Peekskill Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Lake Peekskill holiday rentals

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, (43 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
United States
Heather M.
The price is AU$571
includes taxes & fees
23 Nov - 24 Nov
Contemporary Cozy Cottage
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

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

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
8.0 out of 10, Very good, (3 reviews)
"This home was just as advertised and perfect for a girls weekend getaway. It was clean, cozy and a picture-perfect fall view. Would highly recommend."
United States
Karen W.
The price is AU$910
includes taxes & fees
17 Nov - 18 Nov
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Living area

3. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is AU$282
includes taxes & fees
12 Nov - 13 Nov
Cozy 1-bedroom retreat minutes from West Point!
A historic building with a central tower labeled 'West Point Museum,' featuring a traditional architectural style with multiple windows and a stone facade.

4. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is AU$420
includes taxes & fees
15 Nov - 16 Nov
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A dining area with a table, chairs, a vase with flowers, a hanging light fixture, and wall decorations.

5. Mountain-View 2BR Steps from Thayer Gate

Mountain-View 2BR Steps from Thayer Gate
Highland Falls
The price is AU$481
includes taxes & fees
15 Nov - 16 Nov
Mountain-View 2BR Steps from Thayer Gate
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

6. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.6 out of 10, Exceptional, (21 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
The price is AU$581
includes taxes & fees
12 Nov - 13 Nov
Local Artist Inspired | Walk to WestPoint + King Bed
A hallway with a wooden door, a black table with a sign, and large green plants.

7. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
9.6 out of 10, Exceptional, (4 reviews)
"Clean and convenient near West Point golf course"
United States
mario b.
The price is AU$581
includes taxes & fees
12 Nov - 13 Nov
3BR Near West Point | Coffee Bar | Sleeps 6
A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

8. Perfect 2BR with Free Parking! Walk to West Point!

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
The price is AU$471
includes taxes & fees
16 Nov - 17 Nov
Perfect 2BR with Free Parking! Walk to West Point!
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

9. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
The price is AU$369
includes taxes & fees
12 Nov - 13 Nov
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A modern kitchen with wooden cabinets, a stainless steel stove, a microwave, and a toaster. There are stools and a small island with a plant.

10. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean, modern, functional, comfortable. Great stay"
United States
Jerell T.
The price is AU$388
includes taxes & fees
12 Nov - 13 Nov
Walk to WP Gate + Free Parking!
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

11. 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$518
includes taxes & fees
8 Dec - 9 Dec
Fabulous 3bdrm Home w/parking!
A blue house with a white porch, a welcome sign, and a mailbox.

12. 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.
The price is AU$650
includes taxes & fees
12 Nov - 13 Nov
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.

13. 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$510
includes taxes & fees
8 Dec - 9 Dec
Lovely 3BR Home with parking-Walk to WP Gate!
A house with a view of a bridge and mountains.

14. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (150 reviews)
"We had a great stay!!"
United States
Jasmine
The price is AU$453
includes taxes & fees
17 Nov - 18 Nov
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is AU$681
includes taxes & fees
8 Dec - 9 Dec
Hudson Valley/West Point Retreat w/ parking!
A nighttime view of a residential street with houses, trees, and parked cars.

16. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (95 reviews)
"The host, Maria, was excellent in staying in touch and personally met me upon check-in and checkout. The location is very convenient for walking around downtown or easily drive to nearby outings."
United States
Margaret S.
The price is AU$498
includes taxes & fees
18 Nov - 19 Nov
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A room with a glass table and chairs, a flat-screen TV on the wall, and a view of a beach and buildings.

17. Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (41 reviews)
"Great location very walkable"
United States
Tim B.
The price is AU$345
includes taxes & fees
9 Dec - 10 Dec
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

18. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (9 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is AU$583
includes taxes & fees
19 Nov - 20 Nov
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A brick building with a sign reading 'Lobby' in front.

19. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is AU$133
includes taxes & fees
24 Nov - 25 Nov
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A stone staircase leading to a house with a stone wall and a metal gate.

20. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (28 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is AU$571
includes taxes & fees
14 Nov - 15 Nov
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
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.
View all properties

Find holiday rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Top Lake Peekskill Hotel Reviews

A hotel with a parking lot, a swimming pool, and a view of a lake and mountains.
West Point Motel

West Point Motel

West Point Motel
Highland Falls

8/10 Good

Nice motel
Australia
John
Reviewed September 19, 2025
West Point Motel

Find out more about Lake Peekskill

Everything you need to know about Lake Peekskill holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Lake Peekskill holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lake Peekskill holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Lake Peekskill holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lake Peekskill. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lake Peekskill holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lake Peekskill holiday rentals we have selected for you start as low as AU$282 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Lake Peekskill rentals

At Expedia, we put the best Lake Peekskill holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Lake Peekskill rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lake Peekskill holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lake Peekskill. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Lake Peekskill?

Yes, there are holiday rentals close to the most popular sights in Lake Peekskill, or you can select a more secluded option if you're looking for a relaxing stay.

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

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This holiday home rental outside of Lake Peekskill is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Lake Peekskill?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Lake Peekskill stay.

What’s there to see and do in Lake Peekskill?

While exploring the area, visit family-friendly sights like SplashDown Beach, or get outside and enjoy nature at Oscawana Lake. In the wider area, you’ll find Woodbury Common Premium Outlets and Paramount Hudson Valley Theater.

What’s a holiday rental in Lake Peekskill like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Lake Peekskill. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from public hotel lifts and busy front desks while still allowing you a great travel experience. 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 small group gathering.