Vacation rentals in Chipley

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Top-rated vacation rentals in Chipley

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Guest favorite

A wooden deck is surrounded by tall trees, providing a natural backdrop. A small round table is set with a few plant pots and decorative items. Metal chairs are positioned around the table, inviting moments of relaxation in a serene outdoor setting.

Home in Graceville

4.91 out of 5 average rating, 86 reviews

Cozy & quiet House in the country

Relax with the whole family at this peaceful place. Please note there is NO WI-FI at this location. Feel free to Bring your dog and enjoy a fenced in back yard. We are happy to assist with directions and recommendations! •2 miles from the silos wedding venue . • 14 miles from Falling waters state park ( biggest waterfall in FL) • 29 miles from Florida caverns state park • 33 miles from Ponce de Leon State park • 38 miles from Econfina Creek ( Natural Springs ) • 27miles from Cypress Springs

Guest favorite

An outdoor pool area is enclosed by a white fence, featuring a large blue swimming pool complemented by a spa. Comfortable lounge chairs are arranged around the deck, and a gazebo provides shaded seating. Tall trees and clear blue skies create a serene backdrop.

Guesthouse in Chipley

4.95 out of 5 average rating, 366 reviews

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.

Guest favorite

The exterior of a single-story remodeled home is shown, with a light-colored facade and dark shutters. A welcoming front porch is visible, framed by a spacious lawn surrounded by trees, offering a peaceful rural setting.

Home in Vernon

4.91 out of 5 average rating, 168 reviews

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

Guest favorite

A cozy sleeping area features a spacious bed dressed in white bedding, complemented by a decorative pillow that reads 'Happy.' Natural light enters from a skylight above. Two small nightstands provide storage, and decorative flowers are placed on one of them.

Farm stay in Graceville

4.88 out of 5 average rating, 16 reviews

Let’s Camp - Florida Edition!

Come to a place of grace in Graceville! Enjoy nature and the drink the well water that taps into the natural spring reservoir! We have 5 acres for you to explore with a trail into a majestic forest! Plenty of space for kids to run in a safe location! We are in a central location to Ponce De Leon Springs, Morrison Springs, Florida Cavern State Park and so much more! No pet fee for pets staying outside. Too rural for WiFi, so you can get off your devices and enjoy each other! Happy camping!

Top guest favorite

A wooden dock extends into clear water, featuring a red umbrella that provides shade. A ladder is positioned at the edge of the dock, leading into the lake. The landscape is characterized by lush greenery in the background under a bright blue sky.

Home in Marianna

5 out of 5 average rating, 58 reviews

Lake House near Marianna & Panama City FL

Enjoy a beautiful, serene, restful atmosphere inside & out at this fully equipped lake front home. Amenities include a fully equipped home with linens, towels, kitchen equipment, washer, dryer, a private dock reaching into deep water, kayaks and water toys for your enjoyment. Perfect for family or a group of friends. Excellent fishing & swimming. No gas motors allowed, allowing the spring fed lake to stay pollutant free. RV hook ups & dump station with plenty of parking also available for fee.

Top guest favorite

A welcoming porch is featured at the front of a single-story house, flanked by tall trees and lush greenery. The home has a sloped metal roof and is set against a serene natural backdrop, creating a peaceful atmosphere.

Cottage in DeFuniak Springs

4.89 out of 5 average rating, 107 reviews

Beautiful cottage nestled in the country

Relax with the whole family at this peaceful and serene place to stay. Surrounded by mature trees and beautiful foliage. Quiet and majestic, spend the days at the beach or springs and the nights listening to nature as you star gaze away from the bright lights of the city. Take a nice nature walk down the trails or relax reading a book. A country escape to recharge and just a few miles from town and close to the beach, so you can have the best of both worlds. Your little piece of heaven awaits!

Top guest favorite

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

4.93 out of 5 average rating, 41 reviews

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

Top guest favorite

A charming outdoor porch features two wicker chairs adorned with decorative pillows, positioned around a small blue table. The backdrop displays a vast green field under a clear sky, with trees lining the horizon, creating a peaceful rural setting.

Home in Graceville

4.89 out of 5 average rating, 66 reviews

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.

Guest favorite

The exterior of the house is shown, featuring a porch with a railing and steps leading up to the front door. The house is elevated on pillars, and a black trash bin is placed beside it. Green grass and a sandy area are visible in the surroundings.

Home in Chipley

4.89 out of 5 average rating, 57 reviews

Laceys Way Country house for peace and serenity

Relax with the whole family at this peaceful place to stay. Watch the rabbits and occasionally a deer or two in the front yard. A fenced in area for your pets will give your pets and children some security and safety. This area is a neighborhood but also near the woods. There are neighbor dogs running loose and also the occasional wild animals including eagles, hawks, Osprey, turkey, deer, and coyotes. It's always best to be on the safe side when it comes to your family and furbabies.

Guest favorite

A spacious kitchen area features a large wooden island with seating for three. Modern appliances, including a refrigerator and microwave, are visible against white cabinetry. The high ceiling is enhanced by a gentle fan, and natural light streams in from the nearby door and window.

Barn in Chipley

4.83 out of 5 average rating, 24 reviews

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.

Guest favorite

A spacious living area features a large sectional couch in muted tones, complemented by a rustic wooden coffee table. Large windows allow natural light to fill the room, while a flat-screen television is positioned on a light-colored media console. The entrance door opens to the outside.

Home in Chipley

4.97 out of 5 average rating, 65 reviews

Peaceful Pines

This country home sits on 5 acres with 2 spring fed ponds. Enjoy the great outdoors under the pavilion with picnic tables, a porch swing & grill. There are cards, games & puzzles available for some screen-free time. Since we’re away from the city lights, the night sky is absolutely breathtaking. If you’re looking for privacy and quietness, this is the place to be. * Simple check-out instructions. We just ask that you run the dishwasher & put your trash in the bin.

Guest favorite

An indoor pool is centered in a spacious room with bright blue walls and large windows, allowing natural light to fill the space. Comfortable seating areas are visible on either side, creating a welcoming setting for relaxation or entertainment.

Guesthouse in Chipley

4.9 out of 5 average rating, 21 reviews

Peaceful Romantic Escape, Pool, Spa, 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, 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!