Photo by Kiri Romero

Philipstown vacation rentals

We found 315 vacation rentals — enter your dates for availability

Discover a selection of 32 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

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Find out more about Philipstown

Find out more about Philipstown

Why visit Philipstown

  • Outdoor activities: Philipstown is perfect for hiking, picnicking, and exploring stunning parks and lakes.
  • Scenic beauty: Nestled near the Hudson River, the town offers breathtaking landscapes and nature experiences.
  • Family-friendly atmosphere: With various attractions and accommodations, it's an ideal destination for families.
  • Cultural experiences: Discover local history and unique attractions that highlight the town's charm.
  • Diverse accommodations: Choose from cozy cottages to modern apartments for a comfortable stay.

Popular types of accommodation in Philipstown

If you're looking for the perfect getaway, Philipstown offers a variety of vacation rentals to suit your needs. From cozy cottages to spacious private homes and modern apartments, there’s something for everyone. Whether you're interested in relaxing by the river or exploring local attractions, your stay in Philipstown promises comfort and convenience. Discover the ideal place to unwind, and enjoy everything this charming destination has to offer.

  • Houses: The top choice for travelers in Philipstown, offering spacious and comfortable living for families or groups.
  • Apartments: A popular option for those seeking convenience and a homely feel, ideal for couples or solo travelers.
  • Cottages: Charming and cozy, these rentals provide a quaint escape for a relaxing getaway.
  • Cabins: Perfect for nature lovers, cabins offer a rustic experience amidst the beautiful landscape.
  • Villas: Luxurious and spacious, villas cater to those looking for an upscale stay in Philipstown.**

Top attractions near Philipstown

Philipstown, New York, is a fantastic destination for outdoor enthusiasts and adventure seekers, offering stunning scenery and a variety of attractions. Visitors can explore national and urban parks, as well as beautiful lakes, making it ideal for families and those looking for cultural experiences. Whether you're hiking, picnicking, or simply enjoying nature, there's something for everyone to enjoy in and around Philipstown.

  • United States Military Academy: A prestigious military institution located 5 miles from Philipstown, offering guided tours that showcase its rich history, stunning architecture, and the scenic Hudson River views.
  • Bear Mountain State Park: Situated 9 miles away, this expansive park features hiking trails, picnic areas, and breathtaking views of the Hudson Highlands, perfect for outdoor enthusiasts and nature lovers.
  • Dia Beacon: Located 6 miles from Philipstown, this contemporary art museum features large-scale installations and a serene atmosphere, providing a unique cultural experience along the Hudson River.

Things to do recommended for couples

For a romantic getaway in Philipstown, enjoy a wine tasting at Brotherhood Winery, just 11 miles away, or Benmarl Vineyards and Winery, 12 miles away, both offering charming atmospheres. Don't miss the live music at The Falcon, located 13 miles away, perfect for an entertaining evening together.

Things to do recommended for families

Your family will love the excitement of Michie Stadium, just 3 miles away, where sports enthusiasts can soak in the atmosphere. For a splash of fun, visit SplashDown Beach, 9 miles away, offering thrilling water adventures. Don't miss Peekskill Landing Park, also 9 miles away, perfect for relaxation and wellness.

Things to do recommended for groups

Group travelers in Philipstown can enjoy shopping at Woodbury Common Premium Outlets, just 12 miles away, experience outdoor activities at the Garrison Golf Club, and catch a show at the nearby Eisenhower Hall Theater, only 2 miles away, offering a taste of local culture and entertainment.

*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 you're planning a trip—whether with friends, family, or pets, or if you're considering an extended stay—it's important to prioritize your needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Philipstown with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Philipstown with young kids: Traveling with young kids can be a bit daunting. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, thinking about how close you are to family-friendly attractions is a wise choice.
  • Taking your pets with you to Philipstown: For many families, a vacation isn't truly enjoyable unless their furry companion is by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Philipstown: If you're in search of vacation rentals with special offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Philipstown

Philipstown, New York, is an idyllic destination perfect for outdoor enthusiasts and families seeking adventure and scenic beauty. Nestled near the Hudson River, this picturesque town offers a mix of budget-friendly options and charming neighborhoods, making it an ideal family getaway. Explore local history, enjoy the welcoming atmosphere, and discover unique attractions in and around Philipstown for a memorable vacation experience.

  • Newburgh: Situated a mere 6 miles from Philipstown, Newburgh is a vibrant city that offers a delightful mix of family-friendly activities and urban exploration. Visitors can enjoy shopping at local centers and malls, while also taking advantage of educational venues. Its scenic waterfront along the Hudson River is a perfect spot for outdoor enthusiasts and families alike. Don't miss the chance to visit local landmarks such as the historic sites and the visitor center, which provide insights into the city's rich history and culture.
  • Beacon: Also located 6 miles from Philipstown, Beacon is known for its outdoor adventures and artistic flair. The city is a haven for families and adventure seekers, offering activities like skiing and theater performances. Visitors can explore nearby mountains and parks, perfect for hiking and enjoying nature. Beacon's vibrant arts scene is highlighted by galleries and installations, making it an ideal destination for culture lovers. The scenic views of the Hudson Valley further enhance the travel experience.
  • Fishkill: Just 8 miles from Philipstown, Fishkill is a charming city that combines family-friendly activities with urban conveniences. With a focus on education and shopping, visitors can explore various shopping centers and malls. The area is also home to symbolic landmarks and a theme park, making it a great destination for families. Don't forget to check out the visitor center for more information about local attractions and to plan your visit efficiently.

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 from June to August, 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 SunnyAverageAverage
June67.5°F (19.7°C)Light RainMostly SunnyModerately HighAverage
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 SunnyAverageAverage
November42.6°F (5.9°C)Light RainMostly SunnyAverageAverage
December34.9°F (1.6°C)Light RainMostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

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

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your total booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and accumulate OneKeyCash on eligible bookings. Sign up today and begin saving right away.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient space to plan new trips, pick up where you left off, and manage your travel arrangements. You can easily access the properties you've saved or booked, now organized under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply 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)
  • 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 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:

  • 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)

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 when booking a vacation rental?
When considering a vacation rental in Philipstown, New York, a popular area to stay is Cold Spring. This charming village offers a picturesque setting along the Hudson River and boasts a delightful array of shops, restaurants, and stunning views of the surrounding mountains. The vibrant Main Street is a hub of activity, with cozy cafes and unique boutiques that invite leisurely exploration. The area is particularly appealing for outdoor enthusiasts, as it provides easy access to the scenic Hudson Highlands State Park, great for hiking and enjoying nature.

Another great option is the nearby town of Garrison, which is known for its tranquil atmosphere and beautiful landscapes. Staying in Garrison allows you to experience the natural beauty of the region while being close to attractions like the Bannerman Castle ruins on Pollepel Island, which can be accessed via a short boat ride. Garrison also offers a peaceful retreat with several vacation rental properties that showcase the area's stunning vistas.

Overall, both Cold Spring and Garrison provide a welcoming environment for visitors, each with its unique charm and attractions.
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?
July marks the peak season for visiting Philipstown, attracting travelers eager to enjoy its vibrant summer activities. This period, which extends from July to September, is superb for those who appreciate outdoor adventures, scenic hikes, and cultural experiences in a picturesque setting. With warm temperatures ranging from the mid-60s to low 80s Fahrenheit, visitors can comfortably explore the area's beautiful landscapes and partake in various local events and festivals.

During the summer months, Philipstown comes alive with opportunities for kayaking on the Hudson River, hiking along the scenic trails of the Hudson Highlands, and enjoying the lively atmosphere of local farmers' markets. The charming small-town vibe, combined with outdoor enjoyment, makes this the ideal time for travelers.

For travelers looking for a more budget-friendly option, consider visiting in December. This month provides a great experience, with the town adorned in holiday decorations and a cozy ambiance superb for a winter getaway. While you may encounter colder temperatures, the beauty of the snow-covered landscape offers a different kind of charm, with opportunities for peaceful walks and enjoying local holiday festivities.

Ultimately, the best time to visit Philipstown depends on your preferences for an active summer vacation filled with outdoor adventures or a tranquil winter retreat that highlights the town's festive spirit.
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?
In Philipstown, visitors can enjoy a variety of attractions that highlight the area's natural beauty and historical significance. One of the main draws is the scenic Hudson Highlands State Park, which offers numerous hiking trails with breathtaking views of the Hudson River. The trails in the park, such as those leading to Breakneck Ridge, are popular among outdoor enthusiasts.

The village of Cold Spring, located within Philipstown, features charming shops, art galleries, and waterfront parks along the river, providing a picturesque spot for leisurely strolls. Visitors can also explore the historic Cold Spring Depot, which adds to the area's rich history.

Additionally, the Boscobel House and Gardens, a restored Federal-style mansion, offers guided tours and beautiful landscaped gardens, making it a great destination for history buffs and nature lovers alike. The nearby West Point Military Academy adds an element of historical significance and is accessible for tours, showcasing the area's military heritage.
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 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 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.