Discover Your Perfect Hillsdale Vacation Homes

Hillsdale Large Vacation Homes

10.0 (4 Reviews)
House
Country Karma -Quiet Wooded Getaway
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
View Availability
See More Family Vacation Rentals in Hillsdale on FVR

Why Choose Rent By Owner for your Hillsdale 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 Hillsdale

When should you plan your Vacation Rentals stay?

Choosing the optimal time to plan your trip here ensures you experience the best of what this destination has to offer, as the region's seasonal changes greatly influence the weather and local activities available for your stay.

Peak Season Highlights

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Summer (June to August)

During the peak summer months, you can enjoy warm weather ideal for outdoor activities and exploring the scenic beauty of this region. It’s the most popular time for visitors seeking a lively atmosphere and sunshine-filled days.

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

The fall season offers vibrant foliage and crisp air, making it a favorite among travelers looking for picturesque landscapes and seasonal serenity. This period is perfect for experiencing the area's natural splendor at its best.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Winter (December to February)

Visiting during winter allows you to enjoy quieter surroundings and cooler temperatures, which are ideal if you prefer a peaceful retreat away from the crowds. It’s an excellent time for cozy accommodations and scenic winter views.

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

In spring, the area begins to blossom, offering mild weather and fewer visitors. It’s an inviting time to explore the natural beauty while avoiding peak tourist influx, making your stay more relaxing.

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

Weekly Weather Forecast for Hillsdale

How to Book Your Hillsdale 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 Hillsdale

More Top-Rated Vacation Rentals in Hillsdale 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

  • You can enjoy outdoor seating areas perfect for relaxing and taking in the scenery of the region.
  • Many properties feature spacious decks or patios ideal for dining al fresco after exploring the area.
  • Expect well-maintained gardens or landscaped yards that enhance your outdoor experience.
  • Look for properties with access to private or shared outdoor fire pits for cozy evenings outdoors.
  • Many vacation rentals offer either a swimming pool or hot tub to unwind after a day of adventure.
  • Outdoor grills are commonly available, allowing you to prepare meals while enjoying the fresh mountain air.
  • Some options include direct access to hiking trails or natural scenic spots just outside your door.

Top Attractions Around Hillsdale

What attractions are nearby?

In this charming region, you can enjoy a variety of outdoor activities such as hiking, biking, and exploring scenic nature trails just minutes from your vacation rental in Hillsdale, New York.

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Family Activities

  • Hillsdale Historical Society Museum: Explore local history and engage your family with educational exhibits in this welcoming museum located in the heart of the region.
  • Catamount Aerial Adventure Park: Challenge your family with outdoor fun as you navigate through treetop courses and zip lines amid the scenic views of the surrounding landscape.
  • Millbrook Golf Course: Enjoy a family-friendly round of golf at this scenic course, perfect for both beginners and experienced players seeking a relaxing outdoor activity.
  • Hillsdale Community Park: Spend quality time outdoors with picnicking, playgrounds, and open spaces for games, ideal for families looking to unwind in the area.
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Adult Activities

  • Hiking at Bash Bish Falls State Park: Explore the scenic trails along the border of this destination, offering breathtaking views and a peaceful retreat into nature.
  • Visiting Local Art Galleries: Discover the region's vibrant arts scene by browsing unique exhibitions that showcase local talent and creative expressions.
  • Wine Tasting Tours: Enjoy the region's distinguished wineries with guided tastings that highlight the area's renowned viticultural offerings.
  • Golfing in the Area: Tee off on beautifully maintained courses surrounded by the region's natural beauty for a relaxing day on the links.

Other Places to Stay in Hillsdale, NY

Columbia County
Columbia County Vacation Rentals
Catamount Aerial Adventure Park
Catamount Aerial Adventure Park Vacation Rentals
Town of Copake
Town of Copake Vacation Rentals
Copake Lake
Copake Lake Vacation Rentals
More Places to Stay Near Hillsdale

Hillsdale Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Outdoor Activities: Take advantage of the region's natural beauty by engaging in outdoor pursuits such as hiking or cycling through scenic trails around the area.
  • Visit Nearby Cultural Spots: Discover local art galleries and historical sites to immerse yourself in the area's rich heritage and vibrant community vibe.
  • Plan Your Dining Experiences: Sample regional cuisine at nearby eateries to enjoy authentic flavors that highlight the unique character of this destination.
  • Pack Thoughtfully for the Climate: Be sure to bring appropriate clothing for the area's seasonal weather to maximize your comfort during your stay.

Transportation Options

  • Car Rentals: Renting a car provides the flexibility to explore the scenic region surrounding Hillsdale at your own pace.
  • Local Taxi Services: Reliable taxi services in the area can conveniently transport you from your vacation rentals to nearby attractions and amenities.
  • Public Transportation: Regional bus services connect this destination with neighboring towns, making day trips accessible without a personal vehicle.
  • Shuttle Services: Airport and event shuttles offer seamless transfers for travelers arriving via regional airports or attending local events in the region.

Local Customs Options

  • Local Agricultural Traditions: You will notice that farming and local produce are integral to the area's heritage, reflecting in community events and markets.
  • Historic Preservation Practices: Respect for the region’s history is evident through the preservation of buildings and landmarks important to this destination's identity.
  • Community Gatherings and Festivals: Participating in seasonal festivals showcases the region's cultural pride and offers authentic experiences for visitors.
  • Natural Conservation Etiquette: Visitors are encouraged to follow eco-friendly practices and respect the natural landscapes during outdoor activities here.

Frequently Asked Questions About Hillsdale?

1. What are the top vacation rentals in Hillsdale?

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

2. How many vacation rentals have private pools in Hillsdale?

There are 4 vacation rentals with private pools near Hillsdale. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Hillsdale are best for families?

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

4. How many Rentbyowner vacation rentals are available in Hillsdale?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 147 in the Hillsdale 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 Hillsdale. 

5. What is the cancellation policy for vacation rentals in Hillsdale, New York?

Cancellation policies vary by property, so it is important to review the specific listing details or contact the owner directly to understand the terms and potential fees associated with canceling your reservation.

6. How do I inquire about availability and rates for a vacation rental in Hillsdale?

You can check the availability and rates by visiting the listing and using the booking platform’s inquiry feature or contacting the property owner directly for more detailed information.

7. Are there any additional fees or deposits required when booking a vacation rental in this area?

Additional fees such as cleaning fees, security deposits, or service charges are often listed on the property detail page. Confirm these details with the owner before completing your reservation to avoid surprises.

8. What amenities are typically included in vacation rentals within the region?

Most vacation rentals here offer amenities like Wi-Fi, fully equipped kitchens, and outdoor spaces, but it’s best to review each listing’s amenities section or ask the owner for specifics related to your stay.

9. How do I ensure my booking in Hillsdale meets my needs and preferences?

Carefully read the property descriptions, view photos, and review guest reviews on the listing. If you have special requests, contact the owner directly to confirm that the property can accommodate your needs.