Discover Your Perfect Chipley Vacation Homes

Why Choose Rent By Owner for your Chipley 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 Chipley

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit ensures you can fully enjoy your stay in this charming destination, as the region offers different experiences depending on the season and climate conditions here in Florida.

Peak Season Highlights

spring
Spring (March to May)

During spring, you can enjoy milder temperatures and pleasant weather, making it an ideal time to explore the natural beauty of this destination.

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

In fall, the area experiences cooler temperatures with fewer crowds, providing a peaceful setting for your stay.

Average Temperature Daytime: 78°F - Nighttime: 58°F

Off-Season Highlights

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Summer (June to August)

Summer months tend to be hotter and more humid, but they also offer longer daylight hours perfect for outdoor activities.

Average Temperature Daytime: 90°F - Nighttime: 70°F
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Winter (December to February)

In winter, the region sees cooler temperatures and less tourist activity, which may allow for more relaxed and budget-friendly accommodations.

Average Temperature Daytime: 60°F - Nighttime: 40°F

Weekly Weather Forecast for Chipley

How to Book Your Chipley 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 Chipley

More Top-Rated Vacation Rentals in Chipley 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 fully equipped barbecue area for gatherings in the region.
  • Relax by a private or shared swimming pool, perfect for cooling off during warm Florida days.
  • Take advantage of spacious patios or decks to enjoy the scenic views and the pleasant climate.
  • Explore nearby walking trails or nature paths that provide opportunities for outdoor recreation.
  • Make use of covered porches or verandas to unwind while soaking in the fresh air and local scenery.
  • Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
  • Access well-maintained gardens or landscaped yards ideal for outdoor activities and relaxation.

Top Attractions Around Chipley

What attractions are nearby?

Explore nearby outdoor activities and local attractions that allow you to enjoy the natural beauty and charm of this destination during your stay in Chipley, Florida, USA.

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Family Activities

  • Florida Caverns State Park: Explore the stunning underground limestone caves and enjoy family-friendly hiking trails in this natural wonder of the region.
  • Washington-Holmes Historic Library Museum: Discover local history and participate in engaging educational activities perfect for curious young minds visiting here.
  • Campbellton Landing: Enjoy picnicking, fishing, and relaxing by the waterfront at this scenic spot ideal for family outings in the area.
  • Falling Waters State Park: Experience a unique waterfall, beautiful nature trails, and scenic picnic areas that make for memorable family adventures nearby.
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Adult Activities

  • Washington County Public Library: Dive into local history and enjoy a peaceful environment for reading and relaxing within the region.
  • Old McDonald's Farm: Experience a charming farm visit nearby, perfect for engaging with local agricultural traditions and wildlife.
  • Sunny Hills Golf Course: Play a round of golf in this scenic course, offering an enjoyable challenge amid picturesque surroundings.
  • Chipley Historic District: Stroll through the historic district to explore the area's rich heritage and well-preserved architecture.

Other Places to Stay in Chipley, FL

Sunny Hills
Sunny Hills Vacation Rentals
Lucas Lake
Lucas Lake Vacation Rentals
Wausau
Wausau Vacation Rentals
Northwest Florida Community Hospital
Northwest Florida Community Hospital Vacation Rentals
Washington County
Washington County Vacation Rentals
Falling Waters State Park
Falling Waters State Park Vacation Rentals
More Places to Stay Near Chipley

Chipley Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local natural spots: Take advantage of the region's scenic outdoor areas to enjoy peaceful walks or picnics during your stay.
  • Connect with the community: Engage with local events or markets to experience authentic regional culture and hospitality.
  • Plan your activities in advance: Book tours or outdoor adventures early to maximize your time and ensure availability in this quiet destination.
  • Choose a well-located vacation rental: Select a property that offers easy access to the area's attractions and amenities for a more convenient stay.

Transportation Options

  • Chipley Transit System: This local bus service offers convenient transportation options within the area, making it easy for you to explore nearby attractions and amenities.
  • Regional Airports: The closest commercial airports provide accessible air travel options, connecting you smoothly to major cities both nationally and internationally.
  • Rental Cars: Several car rental agencies operate here, giving you the flexibility to discover the region at your own pace with reliable transportation options.
  • Taxis and Ride-Sharing Services: Available in this destination, these services offer convenient point-to-point transportation, ideal for quick trips around the area.

Local Customs Options

  • Southern Hospitality:** You’ll find that the locals here pride themselves on friendliness and welcoming attitudes, which add warmth to your stay in this charming region.
  • Community Events:** Participating in local festivals and gatherings offers a glimpse into the area's traditions and helps you connect with residents in this welcoming destination.
  • Respect for Nature:** The region values conservation, so be mindful of the environment when exploring outdoor spaces around your vacation rental.
  • Local Cuisine Appreciation:** Enjoy trying regional dishes and supporting small eateries, as food plays a key role in the area's cultural identity.

Frequently Asked Questions About Chipley?

1. What are the top vacation rentals in Chipley?

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

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 32 in the Chipley 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 Chipley. 

4. What is the cancellation policy for vacation rentals in Chipley, Florida?

Cancellation policies vary depending on the property listing. You should review the specific terms listed on the rental page or contact the host directly to understand the refund eligibility and any applicable deadlines.

5. Are there any additional fees I should be aware of when booking a vacation rental in this area?

Additional fees such as cleaning, service charges, or local taxes are typically detailed in the listing. Be sure to check the full fee breakdown before completing your reservation to avoid surprises.

6. How do I confirm the availability of a vacation rental in Chipley, Florida?

Availability details are often updated in real-time on the property listing. If you have specific dates in mind, you can usually send an inquiry to the owner or book directly through the platform’s secure system.

7. What amenities are generally included in vacation rentals here?

Most rentals in this region offer amenities like Wi-Fi, air conditioning, fully equipped kitchens, and outdoor spaces. Specific features are outlined in each listing, so review those details to find a property that meets your needs.

8. Who do I contact if I encounter issues during my stay in these vacation rentals?

For any concerns during your stay, contact the property owner or the support team associated with your booking platform. Contact information is typically provided in your reservation details for prompt assistance.