Shrub Oak Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Shrub Oak holiday rentals

A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

1. 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$429
includes taxes & fees
9 Nov - 10 Nov
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
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, (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$576
includes taxes & fees
10 Nov - 11 Nov
Contemporary Cozy Cottage
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

3. 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$594
includes taxes & fees
11 Nov - 12 Nov
Local Artist Inspired | Walk to WestPoint + King Bed
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

4. 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$385
includes taxes & fees
9 Nov - 10 Nov
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A blue house with a white porch, a welcome sign, and a mailbox.

5. 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$656
includes taxes & fees
11 Nov - 12 Nov
3BR West Point Retreat-3min to Back Gate+ King Bed
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.
The price is AU$448
includes taxes & fees
9 Nov - 10 Nov
Fabulous 3bdrm Home w/parking!
Living area

7. 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$296
includes taxes & fees
8 Dec - 9 Dec
Cozy 1-bedroom retreat minutes from West Point!
A room with a wooden floor, a white door with a number, and a window with blinds.

8. 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$460
includes taxes & fees
9 Nov - 10 Nov
Lovely 3BR Home with parking-Walk to WP Gate!
A wooden coffee table with two decorative planters in a living room.

9. 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$419
includes taxes & fees
9 Nov - 10 Nov
Walk to WP Gate + Free Parking!
A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

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

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
The price is AU$383
includes taxes & fees
9 Nov - 10 Nov
Perfect 2BR with Free Parking! Walk to West Point!
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

11. 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$975
includes taxes & fees
9 Nov - 10 Nov
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A dining area with a table, chairs, a vase with flowers, a hanging light fixture, and wall decorations.

12. Mountain-View 2BR Steps from Thayer Gate

Mountain-View 2BR Steps from Thayer Gate
Highland Falls
The price is AU$383
includes taxes & fees
9 Nov - 10 Nov
Mountain-View 2BR Steps from Thayer Gate
A stone staircase leading to a house with a stone wall and a metal gate.

13. 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$576
includes taxes & fees
9 Nov - 10 Nov
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is AU$480
includes taxes & fees
9 Nov - 10 Nov
Hudson Valley/West Point Retreat w/ parking!
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

15. 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$517
includes taxes & fees
12 Nov - 13 Nov
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A hallway with a wooden door, a black table with a sign, and large green plants.

16. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Clean and convenient near West Point golf course"
United States
mario b.
The price is AU$593
includes taxes & fees
9 Nov - 10 Nov
3BR Near West Point | Coffee Bar | Sleeps 6
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

17. 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$389
includes taxes & fees
9 Nov - 10 Nov
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A brick building with a sign reading 'Lobby' in front.

18. 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$132
includes taxes & fees
25 Nov - 26 Nov
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

19. 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
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is AU$481
includes taxes & fees
9 Nov - 10 Nov
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

20. '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$629
includes taxes & fees
19 Nov - 20 Nov
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
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 Shrub Oak Hotel Reviews

A stone building with a tower, surrounded by a garden with large rocks and various plants.
The Abbey Inn & Spa

The Abbey Inn & Spa

The Abbey Inn & Spa
Peekskill

10/10 Excellent

.
Australia
Hannah
Reviewed September 15, 2025
The Abbey Inn & Spa

Find out more about Shrub Oak

Everything you need to know about Shrub Oak 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 Shrub Oak 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 Shrub Oak holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Shrub Oak holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shrub Oak. 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 Shrub Oak 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 Shrub Oak holiday rentals we have selected for you start as low as AU$116 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Shrub Oak rentals

At Expedia, we put the best Shrub Oak 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 Shrub Oak 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 Shrub Oak 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 Shrub Oak. 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

Are there holiday rentals in Shrub Oak?

Yes, there are holiday rentals close to the most popular sights in Shrub Oak, 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 Shrub Oak has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Shrub Oak offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and kitchenware, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Shrub Oak?

Explore the area and family-friendly sights such as SplashDown Beach, or get out into nature at a spot like Oscawana Lake. Donald J. Trump State Park and Woodbury Common Premium Outlets are a couple of places you'll find in the wider area.

What’s a holiday rental in Shrub Oak like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shrub Oak. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family gatherings.