Photo by Kiri Romero

Philipstown holiday lettings

We found 315 holiday rentals — enter your dates for availability

Discover a selection of 27 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:6 Feb - 13 Feb

Image gallery for complete privacy vacation home [private pool]

Pool
9.8 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)

complete privacy vacation home [private pool]

Newburgh, NY

11% off
Price is £5,096
for 7 nights, 1 home
£728 per night
includes taxes & fees
complete privacy vacation home [private pool]

Find spaces that suit your style

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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)
  • Beekman Golf Course (14.8 mi / 23.8 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:

  • Hudson Highlands State Park (1.3 mi / 2.1 km)
  • Storm King State Park (2.2 mi / 3.6 km)
  • Storm King Art Center (5.6 mi / 9.1 km)
  • Canopus Beach (7.3 mi / 11.7 km)
  • Algonquin Park (8.8 mi / 14.2 km)
  • Lake Mahopac (11.2 mi / 18.1 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, a popular area to stay is the charming neighbourhood of Cold Spring. This picturesque village, located along the Hudson River, boasts an array of rental properties that cater to various preferences and budgets. Visitors to Cold Spring can enjoy stunning views of the river and surrounding mountains, making it an ideal spot for those who appreciate natural beauty.

A top attraction in Cold Spring is the West Point Foundry Preserve, a fascinating site that offers walking trails and historical insights into the area's industrial past. Additionally, the scenic waterfront park provides a lovely setting for leisurely strolls and picnics. With a vibrant local community, Cold Spring also features boutique shops, art galleries, and delightful eateries that enhance its appeal.

Another great option is the area around Beacon, which is just a short drive from Philipstown. Beacon is known for its thriving arts scene and culture, exemplified by the Dia:Beacon art museum, which showcases contemporary art in a former factory setting. The neighbourhood offers a diverse range of holiday rentals, allowing visitors to experience both the quaint charm of the town and the artistic vibrancy that it is known for.
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?
July is the most popular time to visit Philipstown, as it marks the peak season for holiday rentals. During these summer months, particularly from July to September, the charming town comes alive with outdoor activities, including hiking, kayaking, and exploring the picturesque Hudson River. Visitors can revel in the natural beauty of the surrounding landscapes while enjoying the vibrant local culture.

With average temperatures reaching the high 20s Celsius, July offers warm, pleasant weather ideal for outdoor adventures and leisurely strolls along the scenic trails. This is also the superb time to experience the local festivals and events that showcase the region's artistic spirit and community vibe.

For those looking to save a bit on accommodation, consider planning your visit in December. Although this is the low season, Philipstown's winter charm is enchanting, with opportunities for cosy escapes, festive decorations, and a quieter atmosphere to enjoy the town's quaint shops and restaurants.
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 variety of attractions that highlight the area's natural beauty and rich history. The scenic Hudson Highlands State Park offers numerous hiking trails with breathtaking views of the Hudson River, making it a popular spot for outdoor enthusiasts. The park's Breakneck Ridge trail is particularly well-known for its challenging terrain and rewarding vistas.

The charming village of Cold Spring, located along the river, features quaint shops, art galleries, and delightful cafes, providing a lovely atmosphere for leisurely strolls. The Cold Spring Depot is a historic train station that has been transformed into a community hub, further enhancing the village's quaint charm.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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