Cold Spring, NY Ski Chalet Rentals

Cold Spring Ski Chalets

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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Hotel

Countryside Motel

6.2

Good

(50 Reviews)

3 Baths 381.04 ft²

US $150/Night 7 Nights - US $1,050

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Hotel

Countryside Motel

7.2

Very Good

(273 Reviews)

1 Bath

US $103/Night 7 Nights - US $721

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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

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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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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Cold Spring Getaway | Saltwater Pool & Views

Price Dropped

House

Cold Spring Getaway | Saltwater Pool & Views

8.0

Excellent

(1 Review)

4 Bedrooms 2 Baths 8 Guests 1666 ft²

US $694/Night 7 Nights - US $4,860

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House

1780 Hudson Valley Farmhouse

4 Bedrooms 2 Baths 6 Guests 2000 ft²

US $829/Night 7 Nights - US $5,803

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House

Charming Cold Spring escape on 2.75 acres

4 Bedrooms 2 Baths 11 Guests

US $645/Night 7 Nights - US $4,518

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New

Apartment

Beautifully Appointed Apartment in Gothic Victorian in the Heart of Cold Spring

1 Bedroom 1 Bath 2 Guests 1500 ft²

US $199/Night 7 Nights - US $1,391

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House

Hudson Valley Carriage House - Private Pearl

10.0

Exceptional

(8 Reviews)

5 Bedrooms 4 Baths 6 Guests 2400 ft²

US $1,533/Night 7 Nights - US $10,731

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More Top-Rated Ski Chalets in Cold Spring Area

Why Choose Rent By Owner for your Cold Spring Ski Chalets?

What makes our Ski Chalets 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 Cold Spring

When should you plan your Ski Chalets stay?

Finding the ideal time to vacation here ensures you experience the best of the region's winter charm, allowing you to enjoy your ski chalets when the conditions are perfect for a memorable getaway in Cold Spring, New York.

Peak Season Highlights

Winter (December to February)

During the winter months, this area transforms into an ideal destination for enjoying snow-covered landscapes and winter sports. You can expect lively atmospheres and excellent conditions for your ski chalets.

Average Temperature Daytime: Around 25°F to 35°F - Nighttime: Between 10°F and 20°F

Spring Break (March to April)

As the region transitions into spring, it attracts visitors seeking late-season skiing and scenic mountain views. The longer daylight hours provide more time to enjoy your stay in cozy ski chalets.

Average Temperature Daytime: Approximately 40°F to 55°F - Nighttime: Near 25°F to 35°F

Off-Season Highlights

Early Fall (September to October)

In early fall, the area offers cooler temperatures with fewer crowds, making it a peaceful time to book your ski chalets and experience the changing foliage. It’s a quiet period for those wanting a serene escape.

Average Temperature Daytime: Between 60°F and 70°F - Nighttime: About 45°F to 50°F

Late Spring (May to June)

As the snow melts away, this season provides a tranquil atmosphere perfect for off-season visits. It’s an excellent opportunity to explore the area’s natural beauty without the winter rush.

Average Temperature Daytime: From 65°F to 75°F - Nighttime: Roughly 50°F to 55°F

Weekly Weather Forecast for Cold Spring

How to Book Your Cold Spring Ski Chalets

What's our booking process?

Our platform allows you to browse a curated selection of ski chalets. 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 Cold Spring

More Top-Rated Ski Chalets in Cold Spring Area

Common Ski Chalets Amenities

What amenities can you expect?

Our Ski Chalets 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 space with a patio or deck, perfect for relaxing after a day on the slopes in the region.
Take advantage of outdoor dining areas to savor meals amidst the scenic mountain views typical of this destination.
Look for outdoor fire pits or fireplaces to gather around and unwind during chilly evenings in this area.
Many rentals feature spacious yards or gardens, ideal for outdoor activities or simply soaking in the fresh mountain air.
Access to private balconies or verandas offers panoramic vistas of the surrounding natural beauty here.
Some properties include outdoor hot tubs or plunge pools, providing luxurious relaxation after winter adventures.
Explore nearby hiking trails or nature paths directly from your rental, allowing you to immerse yourself in the region's outdoors.

Top Attractions Around Cold Spring

What attractions are nearby?

While staying in your cozy ski chalet, you can explore a variety of outdoor activities nearby, including scenic hiking trails and charming local shops that showcase the area's natural beauty and small-town charm, making it an ideal destination for those seeking adventure and relaxation in this picturesque region.

Family Activities

Visit the Hudson Highlands State Park Preserve: Enjoy a family-friendly hike with scenic views and outdoor adventures in this beautiful park nearby.
Explore Cold Spring's Antique Shops: Discover unique treasures and handcrafted items that offer a memorable shopping experience for all ages.
Take a Riverboat Tour on the Hudson River: Experience the area's natural beauty and fascinating history aboard a leisurely boat trip suitable for families.
Attend Local Festivals and Events: Participate in seasonal festivals and community gatherings that showcase the region's vibrant culture and traditions.

Adult Activities

Hiking along the Hudson Highlands State Park Preserve: Enjoy scenic trail walks with breathtaking views of the river and lush landscape, perfect for experiencing the area’s natural beauty.
Exploring local art galleries and studios: Discover the region's vibrant arts scene by visiting unique galleries showcasing local talent, ideal for a cultural escape.
Dining at farm-to-table restaurants: Savor fresh, locally sourced cuisine at some of the area's acclaimed eateries, making each meal memorable during your stay.
Taking a historic walking tour: Immerse yourself in the region’s rich history through guided or self-guided tours of charming streets and historic landmarks.

Other Places to Stay in Cold Spring, NY

Cold Spring Travel Tips

How Can You Make the Most of Your Stay?

Plan Ahead for Local Events: Check the area's event calendar to align your stay with seasonal festivals or markets that add to your experience in this scenic region.
Explore Nearby Nature Trails: Take advantage of the numerous outdoor trails to enjoy the natural beauty surrounding your ski chalet, enhancing your outdoor adventure here.
Book Your Ski Equipment Early: Secure your gear ahead of time to ensure availability and a smooth start to your winter activities in this popular ski destination.
Utilize Local Dining Options: Discover cozy eateries nearby to indulge in local flavors after a day on the slopes, making your stay more memorable and convenient.

Transportation Options

Personal Vehicles: Renting or driving your own car offers the most flexibility for exploring the area and reaching nearby ski resorts comfortably.
Public Transit: Local bus services provide an affordable and convenient way to navigate the region without the hassle of parking or traffic delays.
Shuttle Services: Private or shared shuttles operate between popular destinations, making it easy to get to ski slopes and accommodations without worry.
Taxi and Rideshare: Taxis and rideshare options like Uber or Lyft are readily available here, providing quick transportation options especially during snowy conditions.

Local Customs Options

Dutchess County Fair This regional event showcases local agriculture and crafts, offering a glimpse into the area's rich rural traditions.
Hudson Valley Cuisine Dining here often involves traditional recipes passed down through generations, emphasizing farm-to-table freshness and seasonal ingredients.
Historic Preservation Practices Locals take pride in maintaining their historic architecture and landmarks, reflecting the region’s appreciation for its cultural heritage.
Community Festivals Throughout the year, residents celebrate with lively festivals that highlight local music, art, and seasonal customs, fostering a welcoming atmosphere for visitors.

Cold Spring Ski Chalets Frequently Asked Questions

1. What are the top Ski Chalets in Cold Spring?

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

2. How many Ski Chalets are available in Cold Spring?

Currently, the total number of properties listed by RBO in 2026 is over 35 in the Cold Spring area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Cold Spring. 

3. What is the cancellation policy for booking a ski chalet in this area?

Cancellation policies vary by listing, so it's essential to review the specific terms provided on the property’s page. For detailed information about refunds and cancellation deadlines, please contact the property owner directly.

4. Are there any additional fees or charges I should be aware of when booking a ski chalet here?

Additional fees such as cleaning, resort taxes, or service charges may apply depending on the property. Check the listing details carefully or reach out to the owner to clarify all costs before completing your reservation.

5. What amenities can I expect at a ski chalet in this destination?

Amenities typically include fully equipped kitchens, fireplaces, Wi-Fi, and outdoor spaces. For specific features available at each property, refer to the individual listing or contact the host directly.

6. Is there a minimum stay requirement for booking a ski chalet in this region?

Many properties have minimum night requirements, especially during peak seasons. Confirm the stay duration with the owner or review the booking policy on the listing for accurate details.

7. How do I ensure my booking is secure and reliable for a stay in this destination?

All bookings are handled through a trusted platform that offers secure payment options and verified listings. For peace of mind, always communicate through the official site and review the host's profile before finalizing your reservation.