Photo by Bibek Magar

Philipstown holiday homes

We found 332 holiday rentals — enter your dates for availability
Discover a selection of 26 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:11 Dec - 18 Dec

Hallway with pocket doors on main floor
View of the dining room
Living room through Mahogany pocket doors
Original mahogany wood work and French Chandliers though out the house
Exceptional
(17 reviews)

Stunning historic Victorian house in Newburgh. Pet friendly

Newburgh

20% off
NZ$9,699
for 7 nights, 1 home
NZ$1,386 per night
includes taxes & fees
Stunning historic Victorian house in Newburgh. Pet friendly
Property grounds
Exterior
Interior
Property grounds
Exceptional
(13 reviews)

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction

8% off
NZ$2,361
for 7 nights, 1 home
NZ$337 per night
includes taxes & fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Dining
Private kitchen
Interior
Dining
Exceptional
(8 reviews)

Modern home w/creek view, steps to town & mountain

Beacon

8% off
NZ$10,951
for 7 nights, 1 home
NZ$1,564 per night
includes taxes & fees
Modern home w/creek view, steps to town & mountain
Private kitchen
Main house. Apt is downstairs to the left.
Second bedroom with two full size beds and large walk-in closet.
Dining
Exceptional
(22 reviews)

Lower level unit in Spectacular Log Home Estate

Marlboro

12% off
NZ$2,614
for 7 nights, 1 apartment
NZ$373 per night
includes taxes & fees
Lower level unit in Spectacular Log Home Estate
Private kitchen
Property grounds
Property grounds
Dining
Exceptional
(7 reviews)

A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley

Holmes

8% off
NZ$4,936
for 7 nights, 1 home
NZ$705 per night
includes taxes & fees
A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley
Pool
Living area
Dining
Private kitchen
Exceptional
(16 reviews)

The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC

Harriman

11% off
NZ$7,955
for 7 nights, 1 home
NZ$1,136 per night
includes taxes & fees
The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC
Winter beauty
Breathtaking View, Situated on Orange Lake
Open floor kitchen, LR, and DR, with panoramic view of lake.
Front of house. Lake in back.
Exceptional
(330 reviews)

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Newburgh

8% off
NZ$5,748
for 7 nights, 1 home
NZ$821 per night
includes taxes & fees
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Interior
Family room
Exterior
Chef’s Kitchen
Exceptional
(21 reviews)

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Carmel

12% off
NZ$7,850
for 7 nights, 1 home
NZ$1,121 per night
includes taxes & fees
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Exterior
Property grounds
Dining
Living area
Exceptional
(8 reviews)

Beautiful 1-bedroom apartment overlooking a pond on a 10 acre farm.

Marlboro

12% off
NZ$2,419
for 7 nights, 1 home
NZ$346 per night
includes taxes & fees
Beautiful 1-bedroom apartment overlooking a pond on a 10 acre farm.
Dining
View from Las Mananitas Mexican restaurant in Brewster
Interior
Country style Kitchen
Exceptional
(118 reviews)

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Carmel

8% off
NZ$3,655
for 7 nights, 1 home
NZ$522 per night
includes taxes & fees
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Interior
Living area
Dining
Room
Exceptional
(28 reviews)

Hudson River Retreat

Newburgh

8% off
NZ$2,674
for 7 nights, 1 apartment
NZ$382 per night
includes taxes & fees
Hudson River Retreat
Exterior
Outdoor spa tub
Dining
Private kitchen
Exceptional
(13 reviews)

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

Cornwall

11% off
NZ$4,183
for 7 nights, 1 home
NZ$598 per night
includes taxes & fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Outdoor dining
Interior
Dining
Interior
Exceptional
(23 reviews)

Peekskill Carriage House Downtown Studio

Peekskill

8% off
NZ$2,577
for 7 nights, 1 home
NZ$368 per night
includes taxes & fees
Peekskill Carriage House Downtown Studio
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Philipstown

  • Stunning scenery: Experience breathtaking landscapes in Philipstown, perfect for outdoor enthusiasts.
  • Family-friendly activities: Enjoy a range of activities suitable for all ages, making it a great spot for families.
  • National and urban parks: Explore beautiful parks that offer both relaxation and adventure amidst nature.
  • Charming local culture: Discover the quaint town vibe and friendly locals that make Philipstown unique.
  • Proximity to attractions: A short drive to vibrant cities and coastal suburbs enhances your travel experience.

Top attractions near Philipstown

Philipstown is perfect for those seeking outdoor adventures and stunning scenery. Explore the national and urban parks, as well as nearby lakes, offering a mix of culture and family-friendly experiences. For a seamless visit, consider checking out a Philipstown map and looking for local activities and accommodation options to enhance your stay.

  • Dia Beacon: A contemporary art museum set in a former factory, Dia Beacon showcases large-scale installations and offers a unique cultural experience. The serene atmosphere invites reflection and appreciation of modern art.
  • Oscawana Lake: A picturesque lake perfect for a relaxing day out. Enjoy stunning scenery, sandy beaches, and opportunities for romantic picnics or outdoor activities like kayaking and swimming.
  • Algonquin Park: An urban park that provides a family-friendly environment with playgrounds and open spaces. It's an ideal spot for picnics, leisurely strolls, and enjoying the vibrant city atmosphere.

Things to do recommended for couples

Looking for a romantic getaway in Philipstown? Visit Brotherhood Winery for a lovely atmosphere, or enjoy live music at The Falcon. Don't miss the enchanting Benmarl Vineyards and Winery, perfect for couples seeking a delightful experience just a short drive away.

Things to do recommended for families

For a family adventure in Philipstown, catch a game at Michie Stadium, dive into fun at SplashDown Beach, or unwind at Peekskill Landing Park. Each spot offers unique experiences, ensuring a memorable time for everyone in the family.

Things to do recommended for groups

Groups visiting Philipstown can indulge in shopping at Woodbury Common Premium Outlets, enjoy a round of golf at Garrison Golf Club, or catch a show at the nearby Eisenhower Hall Theater for 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 it's with a group, family, pets, or for an extended stay—it's important to prioritise your preferences. Here are some helpful booking tips for Vrbo to guide you.

  • Traveling to Philipstown with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or an outdoor area for group get-togethers. The good news is that you can easily filter for all these options and more on Vrbo.
  • Traveling to Philipstown with young kids: Travelling with young kids can be quite a task. It’s important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can make your trip even more enjoyable.
  • Taking your pets with you to Philipstown: For many families, a trip wouldn’t feel complete without their furry companion along for the adventure. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer 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 holiday rentals with discounts 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 long-term rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Philipstown

Philipstown, New York, offers a delightful blend of outdoor adventure and scenic beauty, perfect for a Kiwi getaway. Explore its picturesque town, breathe in the fresh air, and enjoy family-friendly activities. Nearby, you can visit the charming Christchurch and experience the coastal suburb vibes. Just a short drive away, the vibrant city of Colombo beckons with its unique attractions, ensuring a memorable holiday filled with warmth and hospitality.

  • Newburgh: Situated 9.7km from Philipstown, Newburgh presents a delightful urban experience that combines family-friendly activities with outdoor adventures. This charming city offers a variety of attractions, including shopping centres and educational venues. Visitors can enjoy scenic views around the lake, explore the visitor centre, and delve into the area's rich history at local historic sites. With its vibrant community and accessible amenities, Newburgh is a perfect spot for those looking to blend city life with nature.
  • Beacon: Also located 9.7km from Philipstown, Beacon is renowned for its outdoor adventures and family-oriented activities. This lively city is a haven for those seeking thrilling experiences, from skiing in the winter months to enjoying the local theatre scene. Nature enthusiasts will appreciate the beautiful landscapes, including nearby mountains and parks that provide ample opportunities for hiking and relaxation. Beacon's blend of culture and adventure makes it an unmissable destination on your travels.
  • Fishkill: Just 12.9km from Philipstown, Fishkill is a family-friendly city that offers a mix of outdoor fun and urban amenities. Visitors can explore various educational centres and enjoy shopping at local malls. The area is home to symbolic landmarks and a theme park that promises a day of excitement for all ages. With its welcoming atmosphere and diverse attractions, Fishkill is an ideal spot for families looking to make memorable experiences together.

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.

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

Booking with Vrbo is simple

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

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy space for you to plan new adventures, resume from where you paused, or easily view and manage your itineraries. You'll discover your saved or booked properties neatly arranged under Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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:

  • West Point Golf Course (3.4 mi / 5.5 km)
  • 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)

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:

  • Little Stony Point Park (0.8 mi / 1.3 km)
  • 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)
  • Oscawana Lake (5.6 mi / 9.1 km)
  • Fishkill Ridge (5.9 mi / 9.5 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.
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.
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.
Are all fees included in the Philipstown holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Philipstown holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Philipstown holiday homes?
You can find great discounts on holiday homes in Philipstown on Bookabach, 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 change or cancel my Philipstown holiday home booking on Bookabach?
To find Philipstown holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Philipstown?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Philipstown holiday home?
Book your Philipstown holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Philipstown?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Philipstown to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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