Photo by louann ohora

Philipstown Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Our top choices for Philipstown holiday rentals

2.0 star property
The price is AU$1,288
includes taxes & fees
5 Jan - 6 Jan 2026
Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
The price is AU$1,370
includes taxes & fees
5 Jan - 6 Jan 2026
West Point Villa - Jacuzzi Pool BBQ Games Pets
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Philipstown Hotel Reviews

Find out more about Philipstown

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

Philipstown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Philipstown. 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 Philipstown 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 Philipstown holiday rentals we have selected for you start as low as AU$300 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Philipstown rentals

At Expedia, we put the best Philipstown 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 Philipstown 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 Philipstown 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 Philipstown. 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 Philipstown?

Yes, there are holiday rentals in Philipstown close to Manitoga The Russel Wright Design Center, 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 Philipstown has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Philipstown 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.

How many holiday rentals are there in Philipstown?

Choose from 26 Expedia holiday rentals in Philipstown for a memorable holiday.

What can I see and do in Philipstown?

Enjoy the outdoors at Hudson Highlands State Park and Hudson River, or simply take in cultural attractions like Boscobel House and Gardens and Manitoga The Russel Wright Design Center. Other places in town to visit include Clarence Fahnestock State Park and Graymoor - The Holy Mountain.

What’s a holiday rental in Philipstown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Philipstown. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for families.