Vacation rentals in Chipley

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Top-rated vacation rentals in Chipley

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Guest favorite

Home in Graceville

4.9 out of 5 average rating, 51 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

Jun 20 – 27

R1,925 ZAR per night

Guest favorite

Guesthouse in Chipley

4.96 out of 5 average rating, 187 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, two twin bunk beds, and a queen size sleeper sofa, all of which can accommodate a total of 6 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 guests.

Nov 8 – 15

R1,562 ZAR per night

Guest favorite

Home in Vernon

4.91 out of 5 average rating, 102 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

Oct 16 – 23

R3,430 ZAR per night

Guest favorite

Home in Dothan

4.98 out of 5 average rating, 122 reviews

Comfy 3 bedroom house with hot tub and game room.

Relax and unwind in this space, or even come to work or play. You will have the entire 3 bedroom, 2 full bath house to yourselves. Equipped with washer/dryer, kitchen, hot tub, work space, Wi-Fi, and even a little bar with ping pong table & dartboard. This is our house we have been remodeling and use as our own little getaway on date night, it’s far from upscale fancy, but it is cozy and with a soak in the hot tub can even be romantic. Welcome gift provided, message with any special requests.

Jul 13 – 20

R2,533 ZAR per night

Guest favorite

Guest suite in Enterprise

4.98 out of 5 average rating, 466 reviews

BEST VALUE - No Cleaning Fee

"Relaxing, calm, quiet, peaceful"--all used to describe the 1,200 sq. feet of guest space attached to our home--Read a complete description under "The Space." The private guest suite includes a family room, two bedrooms and bath on our micro-farm just 4 minutes from Fort Rucker and Enterprise. Southern hospitality at its best--Read our reviews! Ammenities include personal-size fridge, coffee, microwave, pool table, WiFi, TV, DVD, Wii, games and toys; laundry room; Handicap/ADA accessible;

R1,121 ZAR per night

Guest favorite

Home in Donalsonville

4.98 out of 5 average rating, 129 reviews

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.

Aug 17 – 24

R2,835 ZAR per night

Guest favorite

Apartment in Enterprise

4.99 out of 5 average rating, 159 reviews

"The Clubhouse", Pvt Apt w/Master BR & Kids Loft

I spent 2 years custom building this apartment to be used exclusively as an Airbnb rental. It was handcrafted using tongue and groove pine milled here in Alabama. All of the oak and pine trim were milled in Virginia using my stepfather's personal sawmill with lumber harvested both from my property here in Alabama, and my families property in Virginia. Even the door\drawer pulls and switch plates were hand forged in PA by an Amish guy at his home forge in his basement.

Jul 12 – 19

R1,374 ZAR per night

Guest favorite

Home in Chipley

5.0 out of 5 average rating, 31 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.

Mar 30 – Apr 6

R3,085 ZAR per night

Guest favorite

Cottage in Dothan

4.99 out of 5 average rating, 137 reviews

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.

May 16 – 23

R2,583 ZAR per night

Guest favorite

Farm stay in Chipley

4.88 out of 5 average rating, 51 reviews

Nice Cozy Rural RV

This is a country escape. The RV offers a king-size foam bed with fresh linens, a washer and dryer for your convenience, and a spacious closet. The kitchenette has a full-size fridge and gas stove. Couch pulls out into a bed that offers extra sleeping space for 2(foam top provided to add extra comfort). Everything you need to enjoy a night or week in the country. WiFi,local chanels, roku TV Towels ,basic essentials,dishes, utensils. Kuerig (pods and creamer)

Jun 15 – 22

R1,809 ZAR per night

Guest favorite

Tiny home in Marianna

4.9 out of 5 average rating, 393 reviews

Live Simply Entire Tiny House/Shed conversion

***Extra Care Taken To Protect You!**** Live Simply- This 12 x 24 Tiny House/shed conversion is a perfectly private, quaint little space for your business traveling needs or your weekend getaways offering A/C, heat, refrigerator, microwave, small kitchenette for meal prep with a hot plate and microwave. Two comfy recliners to relax and have some popcorn while watching your Netflix, Prime or Hulu favorites. Also available for longer stays, just ask!

Feb 20 – 27

R1,822 ZAR per night

Guest favorite

Home in Marianna

4.93 out of 5 average rating, 45 reviews

"The Marianna"- Cute Cottage in Historic Downtown

Our cottage is centrally located in downtown Marianna. You will be walking distance to restaurants and shopping. The cottage is uniquely decorated and has all of the amenities you need. There is a large front porch and also a back yard area for enjoying your morning coffee or afternoon sunset. Smart TV's are in the living room and both bedrooms. The bedroom both have queen beds.

Dec 24 – 31

R2,411 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chipley vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Chipley

Guest favorite

Cottage in Marianna

5.0 out of 5 average rating, 85 reviews

Quiet, cozy 1 bdrm cottage near Caverns & Bear Paw

Aug 24 – 31

R2,379 ZAR per night

Guest favorite

Cottage in Cottonwood

4.96 out of 5 average rating, 28 reviews

Cozy Cottage in the Pines

Jan 13 – 20

R1,975 ZAR per night

Guest favorite

Barn in Slocomb

4.92 out of 5 average rating, 12 reviews

Zeke’s House: Bed & Barn Bliss

Aug 19 – 26

R1,349 ZAR per night

Guest favorite

Home in Chipley

4.95 out of 5 average rating, 42 reviews

Latitude Adjustment

Oct 12 – 19

R3,073 ZAR per night

Guest favorite

Home in Chipley

4.87 out of 5 average rating, 38 reviews

Laceys Way Country house for peace and serenity

May 8 – 15

R2,711 ZAR per night

Guest favorite

Farm stay in Slocomb

4.91 out of 5 average rating, 33 reviews

Quiet 2 bedroom home in a country setting.

Jun 17 – 24

R1,938 ZAR per night

Guest favorite

Cottage in Chipley

5.0 out of 5 average rating, 21 reviews

The Fifth Promise - A Crystal Lake Retreat

Apr 22 – 29

R5,912 ZAR per night

Guest favorite

Home in Geneva

4.88 out of 5 average rating, 8 reviews

Haven of Rest

Sep 10 – 17

R1,793 ZAR per night

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Quick stats about vacation rentals in Chipley

Total rentals
10 properties
Local attractions
Walmart Supercenter, Skins & Bubbas BBQ, and Cancun's Mexican Grill
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Total number of reviews
260 reviews
Nightly prices starting at
R950 ZAR before taxes and fees

Vacation rentals in Chipley

Top-rated vacation rentals in Chipley

Home in Graceville

Guesthouse in Chipley

Home in Vernon

Home in Dothan

Guest suite in Enterprise

Home in Donalsonville

Apartment in Enterprise

Home in Chipley

Cottage in Dothan

Farm stay in Chipley

Tiny home in Marianna

Home in Marianna

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Chipley vacation rentals

Other great vacation rentals in Chipley

Cottage in Marianna

Cottage in Cottonwood

Barn in Slocomb

Home in Chipley

Home in Chipley

Farm stay in Slocomb

Cottage in Chipley

Home in Geneva

Quick stats about vacation rentals in Chipley

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore