Photo by Kiri Romero

Philipstown vacation rentals

We found 333 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

Showing deals for:Aug 29 - Sep 5
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Find out more about Philipstown

Find out more about Philipstown

Why visit Philipstown

  1. Outdoor Adventures: Enjoy hiking and exploring beautiful parks and nature reserves near the stunning Hudson River.
  2. Family-Friendly Activities: Philipstown offers a variety of engaging activities suitable for visitors of all ages.
  3. Charming Neighborhoods: Discover the welcoming atmosphere and friendly locals in picturesque communities.
  4. Educational Vibe: Visit local colleges and universities to appreciate the area's rich educational culture.
  5. Comfortable Accommodations: Choose from cozy vacation rentals, apartments, and inviting cottages for a home-like stay.

Popular types of accommodation in Philipstown

Discover the charm of Philipstown with a variety of vacation rentals to suit your needs. From cozy apartments and houses to charming cottages, there’s something for everyone. Whether you're seeking a relaxing getaway or an adventurous holiday, our selection of accommodations ensures you'll find the perfect fit. Explore hotels in Philipstown and enjoy a memorable stay filled with transparency, savings, and reassurance.

  • Apartments: Apartments are the top choice for vacation rentals in Philipstown, offering modern amenities and convenient locations for travelers.
  • Houses: These homes provide a cozy and spacious environment, ideal for families or groups looking for a home-away-from-home experience.
  • Cottages: Quaint and charming, cottages in Philipstown offer a rustic getaway with stunning views and a relaxing atmosphere.
  • Cabins: Perfect for nature lovers, cabins provide a secluded retreat amidst the beautiful landscapes of Philipstown.
  • Caravan Parks: For a unique experience, caravan parks offer a blend of outdoor adventure and community living.**

Top attractions in Philipstown

Philipstown, New York, is a fantastic destination for outdoor enthusiasts and families alike, offering a mix of adventure and cultural experiences. Explore nearby state parks and nature reserves for hiking and outdoor activities. Visit local colleges and universities to soak in the area's educational vibe. Whether you're planning a family getaway or a solo trip, Philipstown provides a delightful blend of nature and community to discover.

  1. United States Military Academy: Located 5 miles from Philipstown, this prestigious military academy offers guided tours showcasing its rich history, stunning architecture, and picturesque grounds along the Hudson River.
  2. Dia Beacon: Situated 6 miles away, this contemporary art museum housed in a former factory features large-scale installations and sculptures, providing a unique cultural experience in a serene setting.
  3. Bear Mountain State Park: 9 miles from Philipstown, this expansive park offers adventurous hiking trails, scenic views, and opportunities for outdoor activities like picnicking and wildlife watching.

Things to do recommended for couples

For a romantic getaway in Philipstown, explore Brotherhood Winery for a cozy wine tasting, catch a live show at Live At The Falcon for some entertainment, or enjoy a luxurious day at The Golf Club at Mansion Ridge. Each spot offers a unique vibe perfect for couples.

Things to do recommended for families

Your family will love the excitement of Michie Stadium, just 3 miles away, and the fun at SplashDown Beach, 9 miles away. For a relaxing day, visit Bowdoin Park, located 12 miles away, where you can enjoy nature and wellness activities together.

Things to do recommended for groups

In Philipstown, groups can shop at Woodbury Common Premium Outlets, enjoy a round of golf at Garrison Golf Club, and catch a show at the nearby Eisenhower Hall Theater. These activities provide a blend of shopping, outdoor fun, and cultural experiences for everyone to enjoy.

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 filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Philipstown with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. The good news is that you can easily filter for all these options and more on Vrbo.
  • Traveling to Philipstown with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Philipstown: For many families, a trip isn't truly fulfilling without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Philipstown: If you're searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. Using the right 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 in Philipstown

Philipstown, New York, offers a delightful blend of outdoor adventures and family-friendly experiences. Nestled near the stunning Hudson River, visitors can explore beautiful parks, hiking trails, and charming neighborhoods. Nearby Putnam Valley and the captivating northern regions provide the perfect country escape, showcasing friendly locals and a relaxing atmosphere. Whether you're looking for budget-friendly activities or memorable adventures, Philipstown is an ideal destination for your next getaway.

  • Tarrytown: Tarrytown is a charming village located 24 miles from Philipstown, rich in history and scenic beauty. Visitors flock to Tarrytown for its family-friendly atmosphere, outdoor activities, and vibrant city experience. The downtown area features delightful shopping options and a variety of theaters to catch a show. Notable attractions include the historic Lyndhurst Mansion and the picturesque waterfront along the Hudson River, making it an ideal spot for leisurely strolls and picnics. With its quaint streets and rich cultural heritage, Tarrytown offers an inviting blend of relaxation and exploration.
  • Newburgh: Situated just 6 miles from Philipstown, Newburgh is a city that combines urban excitement with natural beauty. Ideal for families and outdoor enthusiasts, Newburgh boasts a variety of shopping centers and educational venues. The vibrant waterfront area features several parks, including the scenic Downing Park, and visitors can enjoy stunning views of the Hudson River. Don’t miss the chance to explore the Newburgh Historical Society and the impressive art exhibits at the Ann Street Gallery. With its welcoming community and engaging attractions, Newburgh is a fantastic destination for any traveler.
  • Poughkeepsie: Located 19 miles from Philipstown, Poughkeepsie is a dynamic city that offers a mix of outdoor adventures and family activities. Known for its beautiful parks and scenic views along the Hudson River, Poughkeepsie is perfect for those seeking adventure. Popular attractions include the Walkway Over the Hudson, which provides breathtaking views, and the nearby Vassar College campus, known for its stunning architecture. With shopping areas and recreational opportunities like skiing in winter, Poughkeepsie promises a fun-filled experience for visitors of all ages.

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 February and November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January28.6°F (-1.9°C)Light RainMostly SunnyModerately LowSlightly Low
February30.4°F (-0.9°C)Light RainMostly SunnyModerately LowAverage
March37.8°F (3.2°C)Light RainMostly SunnyAverageAverage
April48.9°F (9.4°C)Light RainMostly SunnyAverageSlightly Low
May59.4°F (15.2°C)Light RainMostly SunnyModerately HighSlightly High
June67.5°F (19.7°C)Light RainMostly SunnyAverageAverage
July73.6°F (23.1°C)Light RainMostly SunnyAverageAverage
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 HighSlightly High
November42.6°F (5.9°C)Light RainMostly SunnyAverageAverage
December34.9°F (1.6°C)Light RainMostly SunnyModerately LowSlightly Low

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming trip? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to narrow down options 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 the whole booking. Being the planner truly has its rewards! When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash™ on eligible bookings. Sign up today and start enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient area for you to plan your next adventures, manage your existing trips, and keep track of your reservations. You’ll find your saved or booked properties organized into categories like Potential, Upcoming, or Current Trips. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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)
  • The Golf Club at Mansion Ridge (14.9 mi / 24 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)
  • Oscawana Lake (5.6 mi / 9.1 km)
  • Fishkill Ridge (5.9 mi / 9.5 km)
  • Algonquin Park (8.8 mi / 14.2 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 most popular type of vacation rental accommodation in Philipstown?
Cottages are the most popular style of vacation rental in Philipstown, according to our data. Even if you’ve got a different idea about what you want, Vrbo has properties in a variety of sizes and shapes. Explore our options to find your perfect fit.
How much does it cost to rent a vacation rental in Philipstown?
Length of stay, property type and season are some things that can influence the price of a vacation home. Simply add your dates of travel to find your dream escape. From cozy country cottages to expansive villas, all Vrbo vacation rentals provide incredible value.
How much does it cost to rent a beach house in Philipstown?
When you travel and the style and size of the property will determine the cost of your beachside vacation rental. Click on your Philipstown travel dates to see all your options on Vrbo. Can’t live without a hot tub, or maybe a private pool? Use our filters to pick the features and amenities you want in your vacation home.
Are there pet-friendly vacation rentals in Philipstown?
Happily, yes. Take your pick of 30 vacation homes that welcome pets in Philipstown on Vrbo. Our furry companions deserve a getaway too, so simply use our search function for pet-friendly vacation rentals to book a pad where Fido can get in on the fun.
Can I rent a house with a pool in Philipstown?
Tick the “pool” box in our handy filter tool and you’ll find nine houses with private pools in Philipstown on Vrbo. Lazy soak or ball games and races? How you spend your free time is up to you when your vacation property comes with its own swimming pool.
What are popular rental amenities in Philipstown?
Some of the most popular rental amenities people are looking for in Philipstown are a nearby river, a fireplace and a garden. Whether you’re hitting the road with your besties, family or even pets, Vrbo vacation properties come with the best amenities for ultimate relaxation with the people who matter most.
Are there large group vacation rentals in Philipstown?
Take your pick of seven vacation properties in Philipstown that can host 10 or more guests. Whether you’re planning a vacation with extended family or an event like a birthday party, there’s enough room to get your favorite people together under one roof.
Are there vacation rentals in Philipstown that welcome kids?
Philipstown has 30 family-friendly vacation rentals. And finding a stay that welcomes kids is simple with Vrbo’s “Properties good for families” filter. Besides having the entire place to yourselves, you can also look forward to conveniences and perks such as dining rooms, private pools and yards.
Are there one-bedroom vacation rentals in Philipstown?
Yes, you can choose from five one-bedroom rentals in Philipstown. Whether you’d prefer a townhouse or an upmarket condo, our one-bedroom properties are just right if you don’t need tons of space. One of the best things about having your own pad? You won’t ever have to share your getaway with strangers.
Can I find two-bedroom vacation rentals in Philipstown?
Philipstown has three two-bedroom vacation properties to pick from. Discover a vacation home with all the space and privacy you’re looking for at a price that won’t break the bank on Vrbo.
Are there vacation rentals with WiFi in Philipstown?
You’ll find 14 vacation rentals with WiFi in Philipstown. If you want to disconnect from daily life on your escape, but still need to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Philipstown?
You’ll have your pick of 26 Vrbo vacation homes with air conditioning in Philipstown providing that gentle, cool breeze and extra comfort level. Enter your dates of travel and then use our filter tool to locate properties with air conditioning.
How old do you have to be to rent a vacation rental in Philipstown?
The minimum age is normally 16, 18 or 21. It can change from property to property on Vrbo, so check the rules of your chosen Philipstown stay before booking.
How long can I rent a vacation rental in Philipstown for?
The length of time you can book a vacation rental in Philipstown varies according to the property. Simply enter your selected dates to look at a list of options offering extended stays. With plenty of features such as full kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to find somewhere just right to call your home away from home in Philipstown.
Does Vrbo offer discounts for vacation homes in Philipstown?
Weekend adventure or a much-needed extended escape, Vrbo has some fantastic deals and discounts in Philipstown to match your style and your budget. Take a look at our weekly and monthly discounts on vacation rentals, or see what’s recently been added with one of our newly listed homes. Whatever it is you’re after, you’ll find the ideal place to stay — without draining your wallet.

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