Photo by Lynette Geisinger

Philipstown vacation rentals

We found 323 vacation rentals — enter your dates for availability

Discover a selection of 21 homes and other vacation rentals in Philipstown that are perfect for your trip. Vacation homes offer the amenities you expect for your family, friends, or furry companion, such as parking and air conditioning. At the end of the day, you're sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Philipstown

Showing deals for:Jun 19 - Jun 26

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Find out more about Philipstown

Why visit Philipstown

  • Outdoor Adventures: Philipstown is ideal for nature lovers, featuring lakeside parks and outdoor activities for the whole family.
  • Cultural Experiences: Visit local attractions like the Chapel Restoration and Brotherhood Winery for a taste of local heritage.
  • Scenic Neighborhoods: Explore charming residential areas, perfect for leisurely strolls and relaxation.
  • Variety of Accommodations: Choose from cozy cottages, spacious homes, and apartments to suit any budget.
  • Family-Friendly Atmosphere: Enjoy a welcoming environment that caters to visitors of all ages.

Popular types of accommodation in Philipstown

Planning a getaway to Philipstown? Exciting times await as you select the perfect place to stay. From charming cottages and spacious houses to cozy apartments and villas, Philipstown offers a variety of accommodations to suit every traveler. Discover the best hotels and rentals for your stay, ensuring comfort and convenience during your visit. Start exploring your options for unforgettable Philipstown stays today.

  • Houses: The top choice for travelers in Philipstown, offering spacious and comfortable accommodations perfect for families or groups.
  • Apartments: A popular option for solo travelers or couples, providing a cozy and convenient stay in the heart of Philipstown.
  • Cottages: Charming and quaint, cottages offer a unique getaway experience immersed in nature.
  • Cabins: Ideal for those seeking a rustic retreat, cabins provide a peaceful escape surrounded by scenic beauty.
  • Villas: Luxurious and spacious, villas are perfect for those looking for upscale amenities and comfort.**

Top attractions in and around Philipstown

Philipstown, New York, is perfect for outdoor and family adventures, featuring attractions like national parks, urban parks, and local medical centers. Visitors can explore top points of interest such as Grasshopper Grove, the Chapel Restoration, Brotherhood Winery, and Michie Stadium. This charming destination offers a blend of culture and outdoor experiences, making it ideal for travelers seeking fun and relaxation in a picturesque setting.

  • Boscobel House and Gardens: This historic site features stunning neoclassical architecture and beautifully landscaped gardens, showcasing the rich cultural heritage of the area. Enjoy guided tours and breathtaking views of the Hudson River.
  • Bear Mountain State Park: Located 9 miles away, this expansive park offers picturesque scenery, hiking trails, and outdoor adventures, perfect for nature lovers and thrill-seekers alike.
  • Dia Beacon: Just 6 miles from Philipstown, this contemporary art museum features large-scale installations in a former factory, providing a unique cultural experience that captivates art enthusiasts.

Things to do recommended for couples

For a romantic getaway in Philipstown, consider a day at The Golf Club at Mansion Ridge, just 15 miles away. Enjoy the luxurious atmosphere while playing a round of golf together, followed by a cozy dinner, making unforgettable memories in a stunning setting.

Things to do recommended for families

Families can explore the scenic trails of the Hudson Highlands, visit the fun and educational Hudson River Museum, or enjoy a day of outdoor activities at the scenic Boscobel House and Gardens. Don't miss the charming local shops and eateries in the area for a true taste of Philipstown.

Things to do recommended for groups

Explore the scenic trails of the Hudson Highlands State Park, perfect for hiking with friends, or enjoy a fun-filled afternoon at the Philipstown Recreation Center, featuring sports and activities for everyone in your group. Don’t miss the charming local shops and eateries for a true taste of the area.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Philipstown

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—be sure to prioritize your preferences in the search filters. Here are some helpful Vrbo booking suggestions for you.

  • Traveling to Philipstown with a group: Think about how many bedrooms you'll require and any additional features you might want, like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Philipstown with young kids: Traveling with young children can be quite a task. It's important to prioritize their comfort and safety, along with having access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Philipstown: For many families, a vacation wouldn’t feel complete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Philipstown: If you're in search of vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Philipstown

Philipstown, New York, is a charming destination perfect for outdoor enthusiasts and families alike. Nestled near beautiful lakeside parks, you can enjoy a variety of adventures while soaking in the friendly, welcoming atmosphere. Explore residential neighborhoods, relax at outdoor seating spots, and make unforgettable memories in this picturesque village. Whether you're seeking budget-friendly options or a touch of luxury, Philipstown offers a delightful experience for every traveler.

  • Newburgh: Located a mere 6 miles from Philipstown, Newburgh is a vibrant city that offers a delightful blend of family-friendly activities and urban experiences. Visitors can explore a variety of shopping destinations, including a shopping mall center and local boutiques. The city is adorned with beautiful landmarks like the scenic lake and a visitor center, perfect for a casual stroll or a family outing. Newburgh's charming streets are also home to historical sites that reflect its rich heritage, making it a great spot for those looking to combine education with leisure.
  • Beacon: Also just 6 miles from Philipstown, Beacon is renowned for its outdoor adventures and creative atmosphere. This city attracts families and thrill-seekers alike, offering activities such as skiing and theater performances. Outdoor enthusiasts can enjoy the stunning views from nearby mountains and relax in beautiful parks. Beacon's art scene is a highlight, with galleries and cultural events that provide a unique glimpse into the local creative community. Whether you’re hiking scenic trails or enjoying a family day at the park, Beacon promises an enriching experience.
  • Fishkill: Situated 8 miles from Philipstown, Fishkill is another fantastic destination for families and urban explorers. The city features a variety of shopping options, including a shopping center and mall, making it a convenient stop for retail therapy. Fishkill is also home to exciting attractions such as a theme park and a bustling tourist precinct, perfect for a day of fun and adventure. Its proximity to natural sites ensures that visitors can enjoy both city-themed experiences and outdoor exploration, making it a versatile destination for all types of travelers.

Best time to go to Philipstown

If you're planning a trip to Philipstown, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in July to August and October, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.6°F (-1.9°C)Light RainMostly SunnyModerately LowAverage
February30.4°F (-0.9°C)Light RainMostly SunnyModerately LowSlightly Low
March37.8°F (3.2°C)Light RainMostly SunnyModerately LowSlightly Low
April48.9°F (9.4°C)Light RainMostly SunnyAverageSlightly Low
May59.4°F (15.2°C)Light RainMostly SunnyAverageSlightly High
June67.5°F (19.7°C)Light RainMostly SunnyAverageAverage
July73.6°F (23.1°C)Light RainMostly SunnyModerately HighSlightly High
August71.6°F (22.0°C)Light RainMostly SunnyModerately HighSlightly High
September64.8°F (18.2°C)Light RainMostly SunnyAverageAverage
October54.3°F (12.4°C)Light RainMostly SunnyModerately HighAverage
November42.6°F (5.9°C)Light RainMostly SunnyAverageAverage
December34.9°F (1.6°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides you with a dedicated space to plan new journeys, refine your travel arrangements, or review and manage your bookings. Your saved or reserved properties are conveniently categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Philipstown getaway

Experience the unique character of Philipstown with a stay in a vacation home rental. This city has something for everyone. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Philipstown

Are you searching for top things to see and do in the area? Venture out of your cozy vacation rental and check out everything that makes Philipstown a fun spot to vacation. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • SplashDown Beach (8.9 mi / 14.4 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)
  • Thunder Ridge Ski Resort (20.1 mi / 32.3 km)

Exploring the natural landscape of Philipstown

Whether you're an adventurous traveler or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Philipstown. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Chadwick Lake Park (10.8 mi / 17.4 km)
  • Lake Mahopac (11.2 mi / 18.1 km)

Transportation options to and around Philipstown

The nearest airport is in Stewart Intl. Airport (SWF), located 8.8 mi (14.2 km) from the city center. If you can't find a flight that works for your travel itinerary, 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, New York, United States of America when booking a vacation rental?
When considering a vacation rental in Philipstown, New York, a popular area to stay in is Cold Spring. This charming village is renowned for its picturesque views of the Hudson River and the surrounding mountains, making it an ideal spot for nature lovers. Cold Spring features a delightful array of shops, galleries, and restaurants, providing a quaint yet vibrant setting. One of the top attractions in the area is the scenic Breakneck Ridge Trail, which offers stunning hiking opportunities and panoramic vistas. Additionally, the Cold Spring Depot, a historic train station, adds to the village's charm and serves as a gateway for visitors traveling from New York City.

Another fantastic option is Garrison, which is situated just across the river. This area is known for its tranquil environment and beautiful landscapes, great for a peaceful getaway. The Garrison Art Center is a highlight, showcasing various exhibitions and community events that celebrate local artists. Visitors can also explore the nearby Boscobel House and Gardens, a stunning estate featuring beautifully landscaped gardens and historical tours.
How much does it cost to rent a vacation home in Philipstown?
Prices for vacation 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 vacation 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 vacation rentals in Philipstown?
A long-stay vacation rental in Philipstown is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Philipstown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Philipstown with parking available—perfect for families or travelers 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 vacation rental?
The best time to visit Philipstown for a vacation rental is during the peak season from July to September. This vibrant period attracts travelers eager to explore the stunning Hudson Valley, with its picturesque landscapes and rich history. July stands out as the most popular month, where visitors can enjoy outdoor activities such as hiking and kayaking, all set against the backdrop of warm summer temperatures typically ranging from the mid-60s to the low 80s Fahrenheit.

During these summer months, Philipstown comes alive with various local events and festivals, providing a lively option superb for families and friends looking to create lasting memories. The Hudson River offers ample opportunities for scenic boat rides, while nearby attractions like the Boscobel House and Gardens provide excellent cultural experiences.

If you're seeking a more budget-friendly option, consider planning your visit in December. While temperatures drop to the 30s to 40s Fahrenheit, this month offers a unique charm with fewer crowds and beautiful winter scenery, superb for cozy gatherings and enjoying the serene beauty of the area.

Ultimately, your choice of when to visit Philipstown will depend on whether you prefer the bustling summer energy filled with adventure or the peacefulness of winter's embrace.
How early should I book a Philipstown vacation rental?
Book your Philipstown vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Philipstown, New York, United States of America?
In Philipstown, visitors can explore a variety of attractions that highlight the area's natural beauty and cultural heritage. The scenic Hudson Highlands provide numerous opportunities for outdoor activities, including hiking and birdwatching, with trails like those in the Hudson Highlands State Park offering stunning views of the river and surrounding mountains.

For history enthusiasts, the Boscobel House and Gardens is a must-see, featuring a beautifully restored Federal-style mansion and picturesque gardens that overlook the Hudson River. Nearby, the West Point Foundry Preserve offers a glimpse into the area's industrial past with its preserved ruins and walking paths along the river.

Additionally, the charming village of Cold Spring, located within Philipstown, boasts boutique shops, art galleries, and waterfront dining options, making it a superb spot for leisurely exploration.
Can I change or cancel my Philipstown home rental booking on Vrbo?
To find Philipstown vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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