Photo by Bibek Magar

Philipstown holiday rentals

We found 330 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:1 Jan - 8 Jan

Room
Private kitchen
Exterior detail
Living area
Exceptional
(9 reviews)

West Point Family Retreat, 5 min walk to Thayer!

Highland Falls

7% off
AU$6,777
for 7 nights, 1 home
AU$968 per night
includes taxes & fees
West Point Family Retreat, 5 min walk to Thayer!
Interior
Exterior
Property grounds
Living area
Exceptional
(13 reviews)

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction

8% off
AU$2,009
for 7 nights, 1 home
AU$287 per night
includes taxes & fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Privacy on the hill
View from Las Mananitas Mexican restaurant in Brewster
Dining
Country style Kitchen
Exceptional
(119 reviews)

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

Carmel

8% off
AU$3,092
for 7 nights, 1 home
AU$442 per night
includes taxes & fees
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Original mahogany wood work and French Chandliers though out the house
View of the dining room
Hallway with pocket doors on main floor
Walk way to back yard from side of the house
Exceptional
(18 reviews)

Stunning historic Victorian house in Newburgh. Pet friendly

Newburgh

20% off
AU$8,305
for 7 nights, 1 home
AU$1,186 per night
includes taxes & fees
Stunning historic Victorian house in Newburgh. Pet friendly
Exterior
Property grounds
Outdoor dining
Living area
Exceptional
(9 reviews)

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

Marlboro

11% off
AU$2,184
for 7 nights, 1 home
AU$312 per night
includes taxes & fees
Beautiful 1-bedroom apartment overlooking a pond on a 10 acre farm.
Second bedroom with two full size beds and large walk-in closet.
Main house. Apt is downstairs to the left.
Dining
Private kitchen
Exceptional
(22 reviews)

Lower level unit in Spectacular Log Home Estate

Marlboro

12% off
AU$2,353
for 7 nights, 1 apartment
AU$336 per night
includes taxes & fees
Lower level unit in Spectacular Log Home Estate
Primary BR
Family room
Exterior
Chef’s Kitchen
Exceptional
(23 reviews)

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

Carmel

12% off
AU$6,715
for 7 nights, 1 home
AU$959 per night
includes taxes & fees
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Living area
Dining
Private kitchen
Room
Exceptional
(14 reviews)

Cozy House 3 Blocks From West Pt

Highland Falls

7% off
AU$4,978
for 7 nights, 1 home
AU$711 per night
includes taxes & fees
Cozy House 3 Blocks From West Pt
Private kitchen
Property grounds
Interior
Dining
Exceptional
(7 reviews)

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

Holmes

8% off
AU$4,027
for 7 nights, 1 home
AU$575 per night
includes taxes & fees
A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley
Private kitchen
Living area
Dining
Outdoor dining
Exceptional
(17 reviews)

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

Harriman

12% off
AU$7,772
for 7 nights, 1 home
AU$1,110 per night
includes taxes & fees
The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC
Room
Interior
Interior
Outdoor dining
Exceptional
(23 reviews)

Peekskill Carriage House Downtown Studio

Peekskill

8% off
AU$2,194
for 7 nights, 1 home
AU$313 per night
includes taxes & fees
Peekskill Carriage House Downtown Studio
Dining
Living area
Outdoor dining
Interior
Exceptional
(29 reviews)

Hudson River Retreat

Newburgh

7% off
AU$2,298
for 7 nights, 1 apartment
AU$328 per night
includes taxes & fees
Hudson River Retreat
Through the front door to spectacular lake beauty
Breathtaking View, Situated on Orange Lake
Winter beauty
Open floor kitchen, LR, and DR, with panoramic view of lake.
Exceptional
(331 reviews)

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

Newburgh

8% off
AU$5,015
for 7 nights, 1 home
AU$716 per night
includes taxes & fees
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Exterior
Outdoor spa tub
Room
Private kitchen
Exceptional
(15 reviews)

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

Cornwall

12% off
AU$3,582
for 7 nights, 1 home
AU$512 per night
includes taxes & fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

  • 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

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:

  • 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)
  • Fishkill Ridge (5.9 mi / 9.5 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, 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 Stayz?
Stayz 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?
Stayz 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 Stayz, 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 Stayz?
To find Philipstown holiday rentals with free cancellation, just use Stayz'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, Stayz 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 Stayz?
Stayz'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 Stayz 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. Stayz offers something for every taste and budget, from affordable homes in Philipstown to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz 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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