Discover Your Perfect Philipstown Vacation Homes

Philipstown Luxury Rentals

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Philipstown Pet Friendly Vacation Rentals

7.0 (3 Reviews)
House
FARMHOUSE With BARN
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
View Availability
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Philipstown Large Vacation Homes

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Why Choose Rent By Owner for your Philipstown Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Philipstown

When should you plan your Vacation Rentals stay?

Choosing the right time to visit can significantly enhance your experience here, allowing you to enjoy the region's natural beauty and local charm at its best throughout the year.

Peak Season Highlights

summer
Summer (June to August)

During the warmest months, you can enjoy the region’s lush landscapes and pleasant weather, making it an ideal time for outdoor activities and exploring local scenery.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

This season offers vibrant foliage and comfortable temperatures, perfect for scenic drives and experiencing the area's natural beauty at its peak.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December to February)

The quieter winter months provide a peaceful retreat with cooler temperatures, ideal for cozy stays and enjoying the tranquility of the region.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
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Spring (March to May)

Early spring brings mild weather and blooming flora, offering a serene atmosphere before the busy summer season begins.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Philipstown

How to Book Your Philipstown Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Philipstown

More Top-Rated Vacation Rentals in Philipstown Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining areas perfect for relaxed meals amidst scenic views of the area.
  • Benefit from a private or shared backyard space ideal for family gatherings or outdoor activities.
  • Relax in a hot tub or spa, offering a soothing retreat after exploring this destination’s natural beauty.
  • Make use of a fire pit for cozy evenings and storytelling under the stars here in the region.
  • Access spacious patios or decks that provide panoramic views of the surrounding landscape.
  • Take advantage of lush gardens or landscaped grounds that add to the outdoor charm of your stay.
  • Utilize outdoor recreational amenities like walking trails, cycling paths, or picnic spots nearby.

Top Attractions Around Philipstown

What attractions are nearby?

Within this scenic region, you can enjoy a variety of outdoor activities such as hiking, exploring local parks, and experiencing the natural beauty that makes this destination a perfect retreat for nature enthusiasts.

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Family Activities

  • Hiking at Clarence Fahnestock State Park: Explore scenic trails and enjoy outdoor adventures suitable for all ages in the expansive natural setting nearby.
  • Visit the Hudson Highlands Nature Museum: Engage your family with educational exhibits and outdoor programs that highlight the region’s rich wildlife and habitats.
  • Explore the historic Cold Spring Village: Discover charming shops, local eateries, and historical sites that provide a fun and educational experience for children and adults alike.
  • Your day at Breakneck Ridge: Experience an exciting outdoor challenge with breathtaking views that make for memorable family outings in this scenic part of the region.
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Adult Activities

  • Hiking at Hudson Highlands State Park: Explore scenic trails and enjoy breathtaking views of the surrounding region, making it a perfect outdoor activity during your stay.
  • Visit Cold Spring Antiques & Artisans Market: Discover unique antiques and handcrafted items that showcase the local charm of this destination in the area.
  • Canoeing and Kayaking on the Hudson River: Experience the tranquil waters with paddle sports that offer both adventure and relaxation along the riverfront.
  • Wine Tasting at Local Vineyards: Savor regional wines at nearby vineyards, providing an authentic taste of the region’s culinary scene.

Other Places to Stay in Philipstown, NY

Graymoor - The Holy Mountain
Graymoor - The Holy Mountain Vacation Rentals
Highlands Country Club
Highlands Country Club Vacation Rentals
Manitoga The Russel Wright Design Center
Manitoga The Russel Wright Design Center Vacation Rentals
Garrison Art Center
Garrison Art Center Vacation Rentals
Constitution Marsh Audubon Center and Sanctuary
Constitution Marsh Audubon Center and Sanctuary Vacation Rentals
Garrison Golf Club
Garrison Golf Club Vacation Rentals
Constitution Island
Constitution Island Vacation Rentals
Chapel Restoration
Chapel Restoration Vacation Rentals
Foundry Dock Park
Foundry Dock Park Vacation Rentals
Nelsonville
Nelsonville Vacation Rentals
Cold Spring
Cold Spring Vacation Rentals
Garrison
Garrison Vacation Rentals
More Places to Stay Near Philipstown

Philipstown Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Gems: Take time to discover hidden spots and authentic eateries in this area to enrich your stay and experience the local culture firsthand.
  • Plan Outdoor Activities: Make the most of the scenic surroundings by scheduling outdoor adventures such as hiking, biking, or leisurely walks that showcase the natural beauty here.
  • Book Early for Popular Properties: Secure your preferred vacation rentals well in advance, especially during peak seasons, to ensure a comfortable and stress-free visit.
  • Utilize Local Resources: Reach out to property hosts or local visitor centers for personalized tips and recommendations tailored to your interests in the region.

Transportation Options

  • New York State Thruway (Interstate 87): This major highway offers convenient access to and from the region, making it easy to explore surrounding areas during your stay.
  • Putnam County Transit Bus Service: The local bus service connects key points within the area, providing an affordable and reliable transportation option for exploring nearby attractions.
  • Private Car Services and Taxis: For personalized travel around here, numerous private car services and taxis are available to ensure a comfortable journey to your vacation rental accommodations.
  • Regional Rail Services: While not directly in the town, regional rail options connecting to larger cities offer additional transportation flexibility for visitors staying in this destination.

Local Customs Options

  • Traditional Highland Games: Experience the local enthusiasm for traditional Highland Games, reflecting the area's Scottish heritage with events showcasing strength and agility.
  • Farmers' Market Practices: Engage in the region's vibrant farmers' markets where buying locally grown produce is a cherished custom, supporting sustainable practices here.
  • Historic Preservation Customs: Appreciate the community’s dedication to preserving historic buildings and landmarks, which maintain the area's unique cultural identity.
  • Seasonal Celebrations: Participate in seasonal festivals and celebrations that highlight the area's natural beauty and foster a strong sense of community here.

Frequently Asked Questions About Philipstown?

1. What are the top vacation rentals in Philipstown?

There are a lot of options in Philipstown. If you plan on staying in the Philipstown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Philipstown:

2. Which vacation homes in Philipstown are best for families?

If you are looking for a family-friendly vacation home in Philipstown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Philipstown:

3. How many Rentbyowner vacation rentals are available in Philipstown?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 82 in the Philipstown area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Philipstown. 

4. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by property, so it's important to review the specific listing details or contact the owner directly to understand their terms and any applicable fees.

5. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning, service charges, or taxes are typically outlined in the listing. Always check the property details or reach out to the owner for clarification before completing your reservation.

6. How do I confirm my booking for a vacation rental in this destination?

Once you select your preferred property, follow the booking process on the site, which usually involves submitting payment and receiving confirmation from the owner. For any issues, contacting the host directly can ensure your booking is secure.

7. Is it possible to modify or cancel my reservation if my plans change?

Modification and cancellation options depend on the property's policies. It's recommended to review these details during booking or speak with the owner to understand your options if your plans change.

8. What amenities are typically available in vacation rentals around this region?

Most listings include common amenities like Wi-Fi, kitchens, and parking. To find specific features, check the property description or contact the owner for more detailed information.