Philipstown Accommodations

House

3-bedroom Cold Spring house with yard, patio, EV charger, AC, hot tub, fire pit

3 Bedrooms 2 Baths 7 Guests

US $340/Night 7 Nights - US $2,380

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'The Glabin’: Garrison Gem w/Hot Tub & Fire Pit

House

'The Glabin’: Garrison Gem w/Hot Tub & Fire Pit

9.8

Exceptional

(4 Reviews)

3 Bedrooms 3 Baths 6 Guests 1700.7 ft²

US $580/Night 7 Nights - US $4,060

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House

Gorgeous Garrison Gem Pool Sauna Hot Tub More

1 Bedroom 1 Bath

US $1,551/Night 7 Nights - US $10,855

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House

Gloves Off Retreat A Quiet Hudson Valley Escape

3 Bedrooms 2 Baths 4 Guests

US $245/Night 7 Nights - US $1,715

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Price Dropped

House

'The Glabin’: Garrison Gem w/Hot Tub & Fire Pit

10.0

Exceptional

(28 Reviews)

3 Bedrooms 2 Baths 6 Guests 1700 ft²

US $501/Night 7 Nights - US $3,504

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House

Charming Home in Cold Spring - 30-min Drive to West Point

10.0

Exceptional

(21 Reviews)

4 Bedrooms 3 Baths 9 Guests

US $388/Night 7 Nights - US $2,716

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House

Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town

10.0

Exceptional

(17 Reviews)

5 Bedrooms 2 Baths 12 Guests 2700 ft²

US $569/Night 7 Nights - US $3,983

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House

Bear Mountain House.

10.0

Exceptional

(15 Reviews)

3 Bedrooms 3 Baths 8 Guests

US $736/Night 7 Nights - US $5,152

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House

Cold Spring Mountain Retreat: Secluded Oasis

10.0

Exceptional

(6 Reviews)

3 Bedrooms 3 Baths 8 Guests 1845 ft²

US $753/Night 7 Nights - US $5,273

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House

Cold Spring Village Maisonette with Pool

10.0

Exceptional

(2 Reviews)

3 Bedrooms 1 Bath 4 Guests 1000 ft²

US $634/Night 7 Nights - US $4,437

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Apartment

Cozy Cold Spring Getaway

10.0

Exceptional

(1 Review)

1 Bedroom 1 Bath 2 Guests

US $220/Night 7 Nights - US $1,541

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House

Hudson Valley's Nature Experience with Incredible Views!

9.8

Exceptional

(9 Reviews)

3 Bedrooms 2 Baths 7 Guests 2400 ft²

US $507/Night 7 Nights - US $3,548

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More Top-Rated Accommodations in Philipstown Area

Why Choose Rent By Owner for your Philipstown Accommodations?

What makes our Accommodations 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 Accommodations stay?

Choosing the optimal time to visit this charming destination can enhance your experience, as seasonal variations in the area offer different opportunities for relaxation and exploration, so consider planning your stay during peak or shoulder seasons to enjoy the best of what here has to offer while ensuring a seamless booking process through trusted property options.

Peak Season Highlights

Late Spring to Early Summer (May to June)

During this time, the area experiences pleasant weather and vibrant natural scenery, making it ideal for outdoor activities and exploring local sights.

Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F

Early Fall (September to October)

This season offers stunning fall foliage and mild temperatures, perfect for enjoying the region’s scenic beauty and peaceful atmosphere.

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

Off-Season Highlights

Winter (December to February)

The winter months bring cooler temperatures and quieter surroundings, providing a serene setting for those seeking a peaceful retreat.

Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F

Late Fall to Early Winter (November)

As the region transitions into winter, fewer visitors arrive, offering a cozy atmosphere with fewer crowds and opportunities for quiet enjoyment.

Average Temperature Daytime: 45-55°F - Nighttime: 35-45°F

Weekly Weather Forecast for Philipstown

How to Book Your Philipstown Accommodations

What's our booking process?

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

Booking Steps

Search Properties

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

Select a Rental

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

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 Accommodations in Philipstown Area

Common Accommodations Amenities

What amenities can you expect?

Our Accommodations 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 a private outdoor seating area where you can relax and take in the scenic views of the region.
Make use of a fully equipped barbecue grill for outdoor dining amidst natural surroundings.
Take advantage of spacious lawns or gardens perfect for outdoor activities or picnics.
Relax on a patio or deck that offers a peaceful setting to unwind after exploring nearby attractions.
Utilize designated fire pits for cozy evenings under the stars in this charming destination.
Access to outdoor recreational features such as hiking trails or nature paths directly from your rental.
Benefit from ample parking spaces coupled with outdoor lighting for convenience and safety during evening hours.

Top Attractions Around Philipstown

What attractions are nearby?

Within this charming region, you can enjoy a variety of outdoor activities such as hiking, biking, and exploring scenic parks, all just moments from your chosen Philipstown accommodation, making it an ideal destination for outdoor enthusiasts seeking a relaxing yet adventurous escape.

Family Activities

Hudson Highlands Nature Museum Engage with the local environment through interactive exhibits and outdoor trails, perfect for family exploration in the area.
Embark on a family-friendly hike that offers breathtaking views and opportunities for outdoor adventure suitable for all ages.
West Point Foundry Preserve Discover this historic site where children can learn about industrial history while enjoying scenic walking paths and picnic areas.
Putnam County Golf Course Spend a fun day on the greens with family-friendly golf activities designed to entertain both beginners and experienced players alike.

Adult Activities

Hiking and Nature Walks Explore the scenic trails and enjoy the natural beauty that surrounds the area, perfect for outdoor enthusiasts seeking a peaceful retreat.
Visit Hudson Highlands State Park Discover breathtaking views and outdoor adventures in this popular state park, ideal for those looking to reconnect with nature.
Explore Local Art Galleries Spend your days immersing yourself in the regional art scene at unique galleries showcasing local talent and creativity.
Dining at Farm-to-Table Restaurants Savor farm-fresh culinary experiences at highly-rated restaurants emphasizing fresh, local ingredients within the region.

Other Places to Stay in Philipstown, NY

Garrison

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Graymoor - The Holy Mountain

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Garrison Art Center

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Highlands Country Club

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Manitoga The Russel Wright Design Center

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Constitution Marsh Audubon Center and Sanctuary

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Constitution Island

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Garrison Golf Club

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Chapel Restoration

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Foundry Dock Park

Explore 70 Properties

West Point Foundry Preserve

Explore 59 Properties

Cold Spring

Explore 34 Properties

More Places to Stay Near Philipstown

Philipstown Travel Tips

How Can You Make the Most of Your Stay?

Explore local outdoor activities: Take advantage of the scenic surroundings by engaging in outdoor pursuits such as hiking or biking to truly experience the natural beauty of the area.
Visit nearby cultural spots: Discover the region's rich heritage and artistic scene by visiting local galleries and historical sites, enriching your stay here.
Plan ahead for dining experiences: Make reservations at popular restaurants to enjoy authentic regional cuisine without the wait during peak times.
Choose flexible accommodations: Opt for a property with versatile amenities to comfortably accommodate your plans, whether relaxing or exploring.

Transportation Options

New York State Thruway (I-87): This major highway offers convenient access to the area for travelers arriving by car from various parts of New York and beyond.
Putnam County Transit: Providing local bus services, this transit option helps you explore the region easily without the need for a personal vehicle.
Hudson Line of Metro-North Railroad: Connecting to nearby cities, this commuter rail service makes it simple to reach here from urban centers such as New York City.
Local Taxi and Rideshare Services: For flexible, on-demand transportation around the region, taxis and rideshare options are readily available for your convenience.

Local Customs Options

Traditional Irish Celebrations: Participating in local St. Patrick’s Day festivities reflects the area's Irish heritage and provides a vibrant way to experience regional customs.
Harvest Festivals: During the fall, you might enjoy the community-led harvest festivals that highlight the region’s agricultural traditions and produce.
Craftsmanship Skills: Engaging with artisans who preserve historical craft methods offers insight into the region's dedication to maintaining its cultural roots.
Local Folk Music: Attending folk music events showcases the area's musical traditions, inviting you to connect with the community’s cultural expression.

Frequently Asked Questions about Philipstown Accommodations

1. What are the top Accommodations 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 Accommodations in Philipstown:

2. How many Accommodations are available in Philipstown?

Currently, the total number of properties listed by RBO in 2026 is over 72 in the Philipstown area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Philipstown. 

3. What is the cancellation policy for accommodations in Philipstown, New York?

Cancellation policies vary depending on the property listing. It is recommended to review the specific cancellation terms provided in the listing details or contact the host directly for clarification.

4. Are there any amenities I should expect when booking here?

Amenities differ by property; please refer to each listing for a comprehensive list of included features such as Wi-Fi, kitchen facilities, parking, and other comforts. Contact the host if you have specific requirements.

5. How do I ensure my booking is secure in this region?

Secure bookings are facilitated through verified listings with trusted payment options. Always read the host's reviews and ensure your booking is made through the official platform for added peace of mind.

6. What are the check-in and check-out procedures for accommodations here?

Check-in and check-out times are specified by each host within the listing. For specific instructions or early/late arrangements, it’s best to communicate directly with the property owner prior to your arrival.

7. Is there a minimum stay requirement for reservations?

Minimum stay requirements can vary between listings. Details are provided in each property's description; if not specified, contacting the host directly will help clarify any length-of-stay restrictions.