Discover Your Perfect Callicoon Vacation Homes

Callicoon Pet Friendly Vacation Rentals

See More Pet-Friendly Vacation Rentals in Callicoon on PetFriendly.io

Why Choose Rent By Owner for your Callicoon 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 Callicoon

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here ensures you can fully enjoy the region's natural beauty and local charm, making your stay in Callicoon, New York, an unforgettable experience.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, you can enjoy the region's lush landscapes and outdoor activities, making it an ideal time for exploring this destination's natural beauty.

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

Autumn brings vibrant foliage and pleasant weather, perfect for experiencing the scenic views and outdoor adventures in this area during peak season.

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

Off-Season Highlights

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Late Winter (February to March)

The late winter period offers a quieter atmosphere for those seeking tranquility and picturesque snowy landscapes in the region.

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

As the region transitions into spring, you’ll find fewer visitors and mild temperatures, ideal for exploring this destination’s scenic charms at a relaxed pace.

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

Weekly Weather Forecast for Callicoon

How to Book Your Callicoon 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 Callicoon

More Top-Rated Vacation Rentals in Callicoon 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 grilling with a supplied barbecue grill, perfect for hosting gatherings in the area’s scenic settings.
  • Relax on spacious private decks or patios that offer stunning views of the surrounding landscape.
  • Take advantage of a bonfire pit for cozy evenings under the stars, ideal for unwinding after exploring here.
  • Make use of outdoor dining areas to savor meals while surrounded by nature’s tranquility.
  • Explore nearby hiking trails and access outdoor adventure equipment available at many properties.
  • Experience outdoor sports amenities such as volleyball courts or basketball hoops, great for active guests.
  • Utilize private yards or gardens for peaceful retreats in the fresh mountain air of this destination.

Top Attractions Around Callicoon

What attractions are nearby?

In this charming destination, you can explore scenic outdoor activities, enjoy local arts and crafts, and experience the tranquil beauty that makes the region a perfect getaway for relaxation and adventure.

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Family Activities

  • Calkill Falls Trail: Embark on a family-friendly hike along this scenic trail to enjoy picturesque waterfalls and lush woodland views in the region.
  • Western Sullivan County Recreation Park: Spend a fun-filled day at this park, featuring playgrounds, sports fields, and picnic areas perfect for outdoor family activities.
  • The River Access Points: Explore the area's beautiful rivers with safe access points for swimming, fishing, or simply relaxing by the water with your loved ones.
  • Local Farmers Markets: Visit nearby markets to experience fresh local produce and artisanal goods, offering a delightful outing for the entire family to enjoy.
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Adult Activities

  • Hiking and Nature Walks: Explore the scenic trails in the area to enjoy the natural beauty and tranquility of this outdoor paradise.
  • Fishing Experiences: Spend a relaxing day casting your line at local lakes and rivers that are renowned for their freshwater fishing opportunities.
  • Visit Local Wineries: Discover the region's thriving wine scene by taking tasting tours at nearby wineries set amidst picturesque landscapes.
  • Enjoy Cultural Events and Festivals: Immerse yourself in the area's vibrant community through seasonal events, live music, and arts festivals held throughout the year.

Other Places to Stay in Callicoon, NY

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More Places to Stay Near Callicoon

Callicoon Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local outdoor activities: Take advantage of the region’s scenic landscapes by engaging in hiking, fishing, or kayaking to fully immerse yourself in the natural beauty here.
  • Visit nearby attractions: Discover the area's hidden gems and cultural spots to enrich your stay and create memorable experiences during your visit.
  • Plan your meals wisely: Sample the locally sourced cuisine at nearby eateries or prepare delicious home-cooked meals using fresh ingredients available close by.
  • Connect with the community: Engage with locals or participate in community events to gain authentic insights and make your trip here more meaningful.

Transportation Options

  • Car Rental Services: Renting a car gives you the flexibility to explore the scenic region around Callicoon at your own pace, especially when staying in one of the area’s charming vacation rentals.
  • Public Transit: Local bus services connect you to nearby towns and attractions, offering an affordable way to navigate this part of upstate New York without the need for a personal vehicle.
  • Taxi and Rideshare: Taxis and rideshare options provide convenient transportation within the area, making it easy to reach local dining, shops, or outdoor activities from your rental property.
  • Private Shuttle Services: Specialized shuttle providers operate in the region, offering direct routes to key points of interest and transportation hubs, ideal for stress-free travel here.

Local Customs Options

  • Local Craftsmanship: Here, you'll notice a deep appreciation for handmade crafts and locally sourced goods that reflect the area's rich cultural heritage.
  • Seasonal Festivals: This destination hosts vibrant seasonal celebrations where community traditions are celebrated through music, food, and local art.
  • Respect for Nature: In this region, residents hold outdoor preservation in high regard, making eco-friendly practices a common part of everyday life.
  • Farm-to-Table Cuisine: You can enjoy meals that showcase fresh, regional ingredients prepared with authentic culinary techniques rooted in local customs.

Frequently Asked Questions About Callicoon?

1. What are the top vacation rentals in Callicoon?

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

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 63 in the Callicoon 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 Callicoon. 

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

Cancellation policies vary depending on the individual property owner. It’s recommended that you review the specific listing details or contact the host directly to understand the terms and any applicable fees.

5. How do I check the availability of a vacation rental in this destination?

You can verify current availability by viewing the property's online calendar or contacting the owner directly through the booking platform for up-to-date information.

6. Are there any additional fees I should expect when booking a rental here?

Additional fees such as cleaning charges, service fees, or taxes are typically outlined in the listing details. Be sure to review these before confirming your reservation.

7. What amenities are commonly available in vacation rentals here?

Most properties offer essential amenities like Wi-Fi, parking, and fully equipped kitchens. Specific features are listed on each property page, so it’s best to review individual listings for precise details.

8. What is the process for checking in and out of a rental in this region?

Check-in and check-out procedures vary by property. Details are usually provided by the host prior to your stay, and some may offer contactless check-in options for added convenience.