Holiday rentals in Chipley

A Taste of Farm Life

Have fun with the whole family at this stylish place. Our two-bedroom two bath home located in the country, surrounded by farm fields, barns and cow pasture. Great for vacations! Just an hour from the World's most beautiful beaches, 6 miles south of Graceville, FL, and 7 miles north of Chipley, Fl. There are two queen beds, and a pack-n-play. There is a highchair, children's table and chairs, dining table, bar, bar stools, couch, and loveseat. Washer and dryer provided. No pets or smoking.

Guesthouse & Pool

This family friendly home is less than 2 miles from Walmart and restaurants. Wifi, Netflix, Starz, Prime video are included with your stay. There is one queen bed, one full bed, a queen size sleeper sofa, & a twin. All of which can accommodate a total of 7 guests. Chipley is located off I-10. It is a 55-minute drive to the beach and a 45-minute drive to Dothan, AL. Falling Waters State Park is 3 miles away. Caverns park 15 miles. No pets & no smoking allowed. Home is sanitized between guests.

Relaxing Retreat | Pool, Spa, Art Studio, Brkfst

Welcome to Camelot’s Master Suite, an elegant countryside retreat designed for comfort and quiet escape. Enjoy complete privacy with a private exterior entrance and no access to the main residence. This spacious suite features a luxurious king bedroom, a separate queen bedroom, and views across 11 beautiful acres. Unwind in the indoor pool, soak in the hot tub, or relax by the fire pit beside the waterfall and pond. Wake up to homemade pancakes and farm-fresh eggs. A perfect relaxing getaway.

Lakefront Home+Private Beach+Firepit+Kayaks+Floats

Escape to this serene lakefront house, with your own private white sandy beach, Kayaks, and a firepit with firewood. It's perfect for families, groups of friends, or couples looking to unwind and enjoy nature. Just 30 minutes from gulf beaches & the international airport, and close to spring-fed creeks, recreation areas, horseback riding, fishing, and caves, this property offers a variety of outdoor activities for everyone. We hope you write your own amazing stories in our slice of heaven.

The Rodeo Inn

Relax with the whole family at this peaceful place to stay. The Rodeo Inn features all things rodeo and country. Nestled near the heart of Graceville and just 30 mins south of Dothan, AL, you are surrounded by a lot of farmland. Wake up to birds chirping and watch beautiful sunsets off the front porch at night. Tons of antique shops near by, as well as natural springs in every direction including The FL state Caverns (underground caves). If you need some quiet time & relaxation, this is it.

The Tiny House of Healing - Rustic Rural Edition

Let the honeybees restore what the locusts have taken! Peaceful ranch-style cottage with loft, full kitchen and bath. King bed on main level with WHITE bedding, queen in loft & recliner. Enjoy a swingset, tree swing, board games, and walking trail. Bring the kids and enjoy the outdoors! Between many springs 🐟 and caverns 🪨 Crisp well water straight from the tap believed to be the same water that flows into the springs! Come rest & recharge 🐎 horses 🦮 dogs & 🐈 cats welcome!

Cozy Cottage in the Pines

Enjoy a quiet stay just outside of town on a farm! Listen to the breeze whisper through the pines and relax in this peaceful country setting. The cottage is 2 miles north of Cottonwood and is just under 10 miles to The Ross Clark Circle in Dothan. Dothan has a lot to do…..shopping, dining, and entertainment. Also, the cottage is only a few miles from the Florida line and the Georgia line if you’re going there for something fun! WiFi is fast so working from the cottage is easy as well!

'The Fly In' Hangar House

Fly into your next adventure at this rustic 4-bedroom, 2.5-bath retreat on a private airstrip. Nestled on 4 serene acres, this haven blends cabin charm with aviation-inspired appeal. Perfect for nature lovers, pilots, and those seeking a unique getaway, this spacious home offers tranquility and endless possibilities. Whether you're unwinding or hosting a special gathering, this property is your ideal destination. Note: Nightly pricing excludes events—please message for event rates.

Cozy Barndominium

This quaint barndo leaves nothing to be desired with its charming, rustic interior and modern amenities. New appliances and all the comforts of home are sure to make your stay as pleasant as possible. This is a 1 bedroom 1 bathroom home with two additional twin beds in the loft. This is a smaller space but is very functional and comfortable. Only 50 minutes from Panama City's white sand beaches and 7 minutes from Chipley, it's conveniently located for those wanting to explore.

Shady Oaks Cabin on the Hill

Nestled in a serene country setting, this is our guest house up the hill from our country home. The Little White Cabin under the oaks is the perfect retreat for anyone seeking peace, charm, and simplicity. A newly painted facade in crisp white, the cabin’s mint-green door and cozy front porch complete with rocking chairs offer the ideal spot to sip your morning coffee or unwind at sunset. Close to local springs and a short 45 min drive to Panama City Beach.

Chipola Woods quiet & cozy near Caverns, Bear Paw

No cleaning fees! Our one & only peaceful, quiet golf cart friendly location conveniently between I-10/US90 yet the Caverns, Bear Paw river float, Merritts Mill Pond, Hinson Nature Preserve, Blue Springs and all shops, cinema, boat launches & restaurants within a 10 min drive. Golfing, beach, & airports within 1 hour. Modern cottage on a private 1/2 acre equipped with large smart TV's in both the living room and bedroom with Prime video.

Cabin close to FL Caverns Pool, WI-FI & Hot Tub

Handcrafted, owner-built cabin in a peaceful rural setting near Marianna, Cottondale, and Chipley. Ideal for guests who enjoy nature-forward stays rather than hotel-style luxury. Relax in the stock tank pool, gather around the outdoor fire area, and explore the local springs and Florida Caverns State Park just 14 minutes away. Located near Hwy 90, guests may occasionally hear light road noise consistent with a rural highway setting.