Places to stay in Chipley

5 out of 5 average rating, 137 reviews

Cottage in Marianna

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 1/2 acre equipped with large smart TV's in both the living room and bedroom with Prime video. Queen pullout sofa w/mattress topper for extra comfort *on request

4.95 out of 5 average rating, 339 reviews

An outdoor seating area is highlighted by a vibrant floral-patterned rug. A low table is centered between a cozy couch and two armchairs, offering a relaxing space under a shaded gazebo. Red and orange cushions add color to the neutral furniture.

Guesthouse in Chipley

Guesthouse & Pool

This family friendly home is less than 2 miles from Walmart and restaurants. Wifi, Netflix, and Prime video are included with your stay. There is one queen bed, one full bed, a queen size sleeper sofa, and 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 and no smoking allowed. Home is sanitized between guest.

4.93 out of 5 average rating, 29 reviews

A serene swimming area features crystal-clear water surrounded by lush greenery. Individuals of various ages are engaged in recreational activities, while a wooden dock is visible on the left side. Sunlight reflects on the water, creating a calming atmosphere.

Tiny home in Graceville

The Tiny House of Healing - Rustic Rural Edition

Let the honey bees restore what the locusts destroyed in your life! Take a step back in time, when there was no wifi, everyone had well water, gardens at everyone's house and God was held in reverence. Put the phone down and get to know each other again or finish writing that book in the quiet. Board games, a swing and walking trail provided. No wifi but usually 1-2 bars of service (so it is possible to use a mobile hotspot) Fully equipped kitchen. King bed, recliner and queen bed in loft

4.92 out of 5 average rating, 154 reviews

Home in Vernon

Entire home with lakefront access

Looking for a tranquil getaway? Come relax in this beautifully remodeled lakeside home, set amidst the peaceful rural surroundings. Whether you enjoy canoeing, kayaking or fishing, the beautiful Hicks Lake awaits you. And if you're craving a day at the beach, Panama City Beach is just a short 45-minute drive away! But that's not all - you're also just minutes away from several breathtaking natural springs, including Cypress Springs, Vortex Springs, Wiliford Springs, and spring-fed Ecofina Creek

5 out of 5 average rating, 145 reviews

The calm waters of Lake Seminole reflect the soft hues of dawn, creating a serene atmosphere. Mist gently rises from the surface, while silhouettes of trees and structures line the shore, offering a peaceful view of the early morning landscape.

Home in Donalsonville

Peaceful & Beautiful Lake Cabin, Boat House/Dock

Located on beautiful Lake Seminole, a short distance from the hosts main house. Includes use of boat house & dock (you'll need your own boat). 2 boat landings within a mile. Across the lake from Lake Seminole State Park. Within 2 miles of gas station, Dollar General & restaurant. 45min to FL ST Caverns. Free wifi. Full Kitchen is equipped with dishes, pots pans, full size oven/range, refrigerator, microwave, coffee maker. Large flat screen TV, screened in porch and back deck near fire pit

4.91 out of 5 average rating, 32 reviews

A spacious single-story home is shown, featuring a gray exterior with white trim. The front porch is accessible by steps, and large windows allow natural light to fill the interior. Lush green grass and young trees surround the property.

Home in Graceville

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 and bar stools, couch, loveseat and rocker. Washer and dryer provided. No pets

Apartment in Ponce de Leon

Tranquil waters reflect the tall, slender trunks of trees, creating a mirrored effect. The lush greenery in the background offers a serene natural setting. The calm surface of the water enhances the peaceful atmosphere of the surroundings.

4.93 out of 5 average rating, 152 reviews

Backyard Bungalow

Bring the whole family to this great place with lots of room to spread out. Less than 5 minutes from Ponce de Leon Spring State park. Only 10 minutes to get to Vortex Springs or Morrison Springs. Drive 45 minutes to the beautiful white sand beaches in Panama City beach, or Grayton beach in Santa Rosa. Make yourself at home and rest and reset in a country atmosphere. We look forward to hosting you. PET FEE is $25. NO CLEANING FEE. This Airbnb is behind our home, where we live.

4.98 out of 5 average rating, 187 reviews

A wooden dock extends into a calm lake, bordered by lush greenery and reflective water. Two fishing structures are visible to the left and right, with a clear sky filled with clouds overhead. Reeds and aquatic plants surround the shoreline.

Home in Donalsonville

The R & R Lake House on Lake Seminole

Fish, Hunt, Grill, or Chill with direct access to the big lake in just 8 minutes by boat.. Lake Seminole contains 37,500 acres of water, and a shoreline of 376 miles. Bass-Masters annual event attracts anglers from all 50 states. The fish include largemouth bass, crappie, chain pickerel, catfish, striped bass and others. Home is nicely decorated with a lake theme. Awesome Sunsets and views of the lake from the screened-in porch, backyard, 80ft dock, and boat house.

4.99 out of 5 average rating, 195 reviews

A screened porch features a cozy seating area with a cushioned sofa, offering views of a serene pond surrounded by greenery. Large windows provide an unobstructed view of the tranquil landscape, reflecting the calm water and tree line.

Cottage in Dothan

Juju’s Pond House on Smith Pond

Take it easy at this unique and tranquil getaway located on 100 acres and nestled quietly on a private pond. The house was originally built in 1921 and in 2018 we had the house moved down to the pond and did a full renovation while preserving as much original character as we could. Enjoy your morning coffee and watch the sunrise from the screen porch swing or one of the docks at the pond. The property has nature trails to explore, fishing, and plenty of wildlife.

5 out of 5 average rating, 4 reviews

An indoor pool area features bright blue walls with white trim, creating a refreshing atmosphere. Large windows allow natural light to fill the space, while a seating area with two couches is visible in the background. Two poolside ladders provide access to the inviting water.

Guesthouse in Chipley

Romantic Country Escape Pool Hot Tub Breakfast

Come and enjoy this beautiful, cozy, and tranquil getaway. Suite has 1 queen bed, kitchenette, bathroom with shower, smart tv. So many things to do on the property like enjoy the indoor pool, outdoor hot tub, 2 fire pits, goldfish pond with sitting area, chicken coop and vegetable garden , outdoor swing, outdoor movie nights, breakfast, and cottage bakery on property. All situated on a beautiful and peaceful country estate. Come and enjoy yourselves!

4.99 out of 5 average rating, 127 reviews

Home in Altha

Wandering Waters Cabin

FISH-HUNT-BIKE-SWIM-KAYAK-GLAMP Come stay on the beautiful Chipola River in the Florida Panhandle. This inviting cabin overlooks the river with a spacious dock that can be used for a variety of water activities. The house is centrally located approximately one hour from Tallahassee, Dothan, and Panama City Beach-the World's Most Beautiful Beaches.

4.92 out of 5 average rating, 192 reviews

A screened porch reveals a serene view of the lush greenery surrounding a wooden deck. The floor displays natural wood planks, while a red table and grill provide a space for outdoor cooking. A gently flowing stream is visible through the mesh railing.

Cabin in Marianna

A beautiful place

Located on the Chipola River in historic Marianna, Fl. 2 canoes available for your use. Large deck you can fish from. Dock on the river for swimming or launching canoes. Home of the World famous Florida Caverns State Park. Also one of Florida's biggest blue holes "Blue Springs". Only 1 hour from Panama City Beach.

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Popular amenities for Chipley places to stay

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Other great vacation rentals in Chipley

4.89 out of 5 average rating, 87 reviews

A bathroom with turquoise walls features a white toilet and a small sink with a decorative faucet. A mirror is mounted above the sink, reflecting the room's brightness. A window with light blue curtains allows natural light to enter, enhancing the open feel.

Cottage in Bonifay

#2 Cozy cottage in small town USA close to city

SusanRating, 5 stars2 weeks ago

Cottage was great! Roomy, homey, and at a great price! Super clean and had everything we needed. Convenient location close to the main road for us to travel to each of our destinations. 10/10 would stay here again!

4.96 out of 5 average rating, 89 reviews

A peaceful rural landscape is depicted, featuring a herd of cows grazing in a green field. Behind the cows, trees provide a natural backdrop, while a water trough is visible in the foreground, adding to the serene atmosphere of the countryside.

Tiny home in Ashford

Barndo“mini”um

Melissa & JohnRating, 5 stars1 week ago

OMG 🤩 another great stay. A perfect place to get your Zen on. Comfortable and cozy place to unwind from the hustle and bustle.

4.75 out of 5 average rating, 24 reviews

A shimmering swimming pool is set within a fenced area, bordered by a spacious deck. Lush green grass and trees are visible in the background under a clear blue sky.

Home in Graceville

Little Blue Farm: 50+ Acres

Carlos AlbertoRating, 5 stars1 month ago

great house and quiet neighborhood, the pool wasn't available to use at the time of our stay.

4.89 out of 5 average rating, 61 reviews

A charming porch features a small round table and two white chairs, surrounded by potted plants. The entrance, framed by wood beams, leads to a door with a window above it, providing a welcoming access point to the barn unit.

Barn in Slocomb

Zeke’s House: Bed & Barn Bliss

LeighRating, 5 stars1 week ago

Beautiful and peaceful place and Debbie is very kind and communicative. Also enjoyed seeing host interact with her animals - horses, dogs, & the sweetest cow - extraordinary experience in all ways.

4.98 out of 5 average rating, 206 reviews

An airy interior showcases a vibrant yellow door, leading to a bright space with wooden ceilings and a loft area. A compact kitchen features a refrigerator and modern appliances. A ladder provides access to the loft, while a small table and light green seating create functional areas.

Cottage in Lynn Haven

Pace e Amore - Adorable 1 Bedroom Cottage

SamarahRating, 5 starstoday

This little home was great for my Fiancé & I for 5 days. The host were very kind & super quick to respond to messages. We appreciated how clean & comfortable everything was as well!! The photos definitely do this little home justice, it’s just as described and looks exactly like the photos. Our favorite part about it was how big the shower was, and the fact there are 2 air conditioners in the house to make sure it’s kept cool downstairs, and up in the loft where you sleep. Thanks so much for sharing with us, we will be back!😊

5 out of 5 average rating, 49 reviews

An open living space features a modern kitchenette with a granite countertop and two stools. A large flat-screen television is mounted on the wall opposite a spacious bed. Natural light filters through a window, illuminating the soft blue walls and light-colored wood ceiling.

Tiny home in Southport

Tropical Tiny House

LizzieRating, 5 stars1 week ago

The Tiny House was perfect for us!! Just the right size. We spent the daylight hours in PCB and the evening hours in a nice cool spot.

5 out of 5 average rating, 75 reviews

A screened-in Florida room features a spacious dining table surrounded by comfortable seating, illuminated by string lights. Large windows provide views of the surrounding nature, while plants add a touch of greenery to the space. Soft decor enhances the area’s inviting ambiance.

Home in DeFuniak Springs

The Cove on Juniper

RayRating, 5 stars3 days ago

This stay was nothing short of perfect. Beginning with the home, everything about it was HOME. We ended up not using the downstairs bedroom. The living room was very spacious and the couch and loveseat were extremely comfortable. The blankets in the living room had quite a strong odor, but nothing that wasn’t solved with a trip through the washer. The screened in back porch was the highlight of the trip for my wife and I. Morning coffee and meal time took place out there and it was so peaceful and perfect. The upstairs king bedroom was great with the additional air unit up there to help keep things cool. We fought the fitted sheet every night, though. It didn’t fit quite right, but the bed was very comfortable. The upstairs double full bedroom was very accommodating for our two boys. The downstairs bathroom was wonderful, minus the inside shower curtain being a few sizes too small. We had to be sure and be conscious of water getting out. But overall, this home was PERFECT for us.