Photo by Lynette Geisinger

Philipstown holiday lettings

We found 321 holiday rentals — enter your dates for availability

Discover a selection of 23 homes and other holiday rentals in Philipstown that are perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as a hot tub and a washer and dryer. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Philipstown

Showing deals for:12 Jun - 19 Jun

Image gallery for West Point Family Retreat, 5 min walk to Thayer!

Exterior
9.8 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

West Point Family Retreat, 5 min walk to Thayer!

Highland Falls

8% off
Price is £3,374
for 7 nights, 1 home
£482 per night
includes taxes & fees
West Point Family Retreat, 5 min walk to Thayer!

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

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    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Philipstown getaway

Learn about the unique charm of Philipstown with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Philipstown

Do you want to discover things to do during your stay? Venture out of your cosy holiday rental and check out everything that makes Philipstown a one-of-a-kind holiday spot. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • SplashDown Beach (8.9 mi / 14.4 km)
  • Putnam County Golf Course (10.2 mi / 16.5 km)
  • Ice Time Sports Complex (10.7 mi / 17.2 km)
  • Brotherhood Winery (11 mi / 17.7 km)
  • Benmarl Vineyards and Winery (11.8 mi / 19.1 km)
  • City Winery Hudson Valley (16.1 mi / 25.9 km)

Exploring the natural landscape of Philipstown

Whether you're an active traveller or just want to take in the scenery, Philipstown is a great place to get outside. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Boscobel House and Gardens (0.9 mi / 1.5 km)
  • Hudson Highlands State Park (1.3 mi / 2.1 km)
  • Storm King State Park (2.2 mi / 3.6 km)
  • Algonquin Park (8.8 mi / 14.2 km)
  • Lake Mahopac (11.2 mi / 18.1 km)
  • Lake Welch Beach (14.5 mi / 23.3 km)

Transport options to and around Philipstown

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 8.8 mi (14.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 24.3 mi (39.1 km) away.

Frequently asked questions

What is the best area to stay in Philipstown when booking a holiday rental?
When considering a holiday rental in Philipstown, New York, the area around Cold Spring is an excellent choice. This charming village offers a picturesque setting along the Hudson River, with stunning views of the surrounding mountains. Cold Spring is known for its vibrant arts scene and historic architecture, making it a delightful place to explore. You'll find a variety of properties, ranging from quaint cottages to more modern homes, all within walking distance of the village's amenities.

One of the top attractions in Cold Spring is the scenic waterfront park, where visitors can enjoy leisurely strolls or picnics while taking in the breathtaking landscape. Additionally, the nearby West Point Museum offers a fascinating glimpse into military history and is a great spot for those interested in learning more about the area's past. The combination of natural beauty and cultural experiences makes Cold Spring a standout option for holiday rentals in Philipstown.
How much does it cost to rent a holiday home in Philipstown?
Prices for holiday rentals in Philipstown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Philipstown to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Philipstown holiday house rentals?
You can find great discounts on house rentals in Philipstown on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay holiday rentals in Philipstown?
A long-stay holiday rental in Philipstown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Philipstown holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Philipstown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
When is the best time to visit Philipstown for a holiday rental?
The best time to visit Philipstown for a holiday rental is during the peak season from July to September. This lively period attracts travellers looking to enjoy the breathtaking views and outdoor activities that the Hudson Valley has to offer. July, in particular, is a popular month, as visitors flock to the area to take advantage of warm temperatures and numerous local festivals.

During these summer months, you can expect temperatures ranging from the mid-teens to low twenties Celsius, creating great conditions for hiking, kayaking, and exploring the charming towns nearby. Philipstown's proximity to the Hudson River means you can partake in scenic boat rides or simply relax by the water, soaking in the stunning surroundings.

For those seeking a more budget-friendly option, consider planning your visit in December. The winter months offer a unique charm, with opportunities for cosy getaways, and you may find more affordable rental options. Embrace the tranquillity of the season while enjoying winter walks through the picturesque landscape.

Ultimately, your choice depends on whether you prefer the vibrant summer atmosphere filled with activities and events or the peaceful winter months ideal for relaxation.
How early should I book a Philipstown holiday rental?
Book your Philipstown holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Philipstown?
In Philipstown, visitors can enjoy a blend of natural beauty and historical charm. The scenic Hudson Highlands State Park is a major draw, offering numerous hiking trails with breathtaking views of the Hudson River and surrounding landscapes. The area is also home to the charming village of Cold Spring, where you can explore quaint shops and cafes along Main Street, as well as the picturesque waterfront.

For history enthusiasts, the West Point Foundry Preserve is an intriguing site, showcasing remnants of the industrial past and scenic walking paths. Additionally, the nearby Boscobel House and Gardens provides a glimpse into early American architecture and beautifully landscaped grounds, making it a lovely spot for leisurely strolls.

The nearby Constitution Marsh Audubon Centre and Sanctuary is great for birdwatchers and nature lovers, providing opportunities for peaceful walks and wildlife observation.
Can I change or cancel my Philipstown home rental booking on Vrbo?
To find Philipstown holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Philipstown holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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