Best Vacation Homes in Philipstown
House
10.0(29 Reviews)
3 Bedrooms
2 Baths
6 Guests
1700 ft²
Hot Tub
Parking
Balcony/Terrace
Kitchen
US $701/Night
7 Nights - US $4,905
House
9.8(4 Reviews)
3 Bedrooms
3 Baths
6 Guests
1700.7 ft²
- Hot Tub
- Parking
View
Internet
US $571/Night
7 Nights - US $3,995
Cottage
1 Bedroom
1 Bath
- Balcony/Terrace
- Kitchen
Air Conditioner- Internet
US $540/Night
7 Nights - US $3,780
House
10.0(22 Reviews)
4 Bedrooms
3 Baths
9 Guests
- Hot Tub
- Balcony/Terrace
- Air Conditioner
- Internet
US $454/Night
7 Nights - US $3,176
Ski Chalet
1 Bedroom
1 Bath
8 Guests
2497.23 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $780/Night
7 Nights - US $5,458
House
10.0(19 Reviews)
5 Bedrooms
2 Baths
12 Guests
2700 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $571/Night
7 Nights - US $3,998
Condo
10.0(19 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $479/Night
7 Nights - US $3,353
House
10.0(16 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $831/Night
7 Nights - US $5,815
Philipstown Luxury Rentals
House
8.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,717/Night
7 Nights - US $12,019
House
9.8(6 Reviews)
3 Bedrooms
1 Bath
8 Guests
Private Pool- Hot Tub
- Parking
Pool
US $1,196/Night
7 Nights - US $8,370
House
3 Bedrooms
2 Baths
6 Guests
2302 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,079/Night
7 Nights - US $7,553
House
4 Bedrooms
2 Baths
11 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $1,052/Night
7 Nights - US $7,364
House
4 Bedrooms
2 Baths
6 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $878/Night
7 Nights - US $6,146
House
9.8(8 Reviews)
3 Bedrooms
3 Baths
8 Guests
1845 ft²
- Private Pool
- Parking
- Pool
- Kitchen
US $641/Night
7 Nights - US $4,490
House
9.8(11 Reviews)
3 Bedrooms
2 Baths
7 Guests
2400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $604/Night
7 Nights - US $4,226
House
10.0(2 Reviews)
3 Bedrooms
1 Bath
4 Guests
1000 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $598/Night
7 Nights - US $4,184
Philipstown Pet Friendly Vacation Rentals
New
House
3 Bedrooms
2 Baths
5 Guests
1100 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $418/Night
7 Nights - US $2,925
Hotel
8.7(250 Reviews)
9 Baths
211.69 ft²
Breakfast- Parking
- Air Conditioner
- Internet
US $211/Night
7 Nights - US $1,474
Cottage
1 Bedroom
1 Bath
- View
- Kitchen
- Air Conditioner
- Internet
US $338/Night
7 Nights - US $2,366
New
House
3 Bedrooms
1 Bath
7 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $372/Night
7 Nights - US $2,607
New
Ski Chalet
3 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $445/Night
7 Nights - US $3,118
House
10.0(4 Reviews)
4 Bedrooms
3 Baths
9 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $429/Night
7 Nights - US $3,003
House
10.0(1 Review)
5 Bedrooms
2 Baths
14 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,368/Night
7 Nights - US $16,574
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
Pet Friendly
Child Friendly
US $298/Night
7 Nights - US $2,086
Philipstown Large Vacation Homes
House
10.0(8 Reviews)
5 Bedrooms
4 Baths
6 Guests
2400 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,533/Night
7 Nights - US $10,731
House
10.0(6 Reviews)
5 Bedrooms
4 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $980/Night
7 Nights - US $6,860
House
10.0(4 Reviews)
6 Bedrooms
5 Baths
11 Guests
3192 ft²
- Hot Tub
- Parking
Spa- Balcony/Terrace
US $781/Night
7 Nights - US $5,465
House
10.0(3 Reviews)
5 Bedrooms
1 Bath
10 Guests
3600 ft²
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $1,201/Night
7 Nights - US $8,410
House
10.0(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,200/Night
7 Nights - US $8,400
House
5.0(1 Review)
5 Bedrooms
4 Baths
11 Guests
Ocean View- Balcony/Terrace
- View
- Kitchen
US $671/Night
7 Nights - US $4,697
House
3.4(3 Reviews)
5 Bedrooms
2 Baths
12 Guests
3000 ft²
- Spa
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $500/Night
7 Nights - US $3,500
House
5 Bedrooms
5 Baths
14 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $8,889/Night
7 Nights - US $62,222
Why Choose Rent By Owner for your Philipstown Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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 (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
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
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
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.
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.
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.
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
Garrison
Graymoor - The Holy Mountain
Garrison Art Center
Highlands Country Club
Manitoga The Russel Wright Design Center
Constitution Marsh Audubon Center and Sanctuary
Constitution Island
Garrison Golf Club
Chapel Restoration
Foundry Dock Park
West Point Foundry Preserve
Cold Spring
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.
Philipstown Vacation Rental Frequently Asked Questions
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:
- 'The Glabin’: Garrison Gem w/Hot Tub & Fire Pit
- Charming Home in Cold Spring - 30-min Drive to West Point
- Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town
- 2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!
- Bear Mountain House.
- A well-appointed cottage in the woods of Garrison, NY
- Cold Spring Village Maisonette with Pool
- Idyllic Garrison Retreat — Autumn Escape with Fireplace & Spacious Outdoors
- Hudson Valley's Nature Experience with Incredible Views!
- Cold Spring Mountain Retreat: Secluded Oasis
2. How many vacation rentals have private pools in Philipstown?
There are 1 vacation rentals with private pools near Philipstown. Top-rated RBO homes that have access to a swimming pool include:
3. 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:
4. How many Rentbyowner vacation rentals are available in Philipstown?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 90 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
Philipstown Top Rated Vacation Rentals
House
8.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
1666 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $547/Night
7 Nights - US $3,827
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $137/Night
7 Nights - US $958
Cottage
9.6(37 Reviews)
2 Bedrooms
1 Bath
8 Guests
- Hot Tub
- Breakfast
- Parking
- Pool
US $222/Night
7 Nights - US $1,551
Other
4.8(26 Reviews)
7 Bedrooms
7 Baths
24 Guests
4200 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $549/Night
7 Nights - US $3,843
House
1 Bedroom
1 Bath
- Parking
- Pool
- Spa
- Balcony/Terrace
US $1,551/Night
7 Nights - US $10,855
House
5 Bedrooms
3 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $1,399/Night
7 Nights - US $9,793
US $1,168/Night
7 Nights - US $8,176
House
5 Bedrooms
8 Baths
10 Guests
- Private Pool
- Hot Tub
- Pool
- Kitchen
US $1,000/Night
7 Nights - US $7,000
