Vacation rentals in Chipley

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Top-rated vacation rentals in Chipley

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Graceville

4.92 out of 5 average rating, 48 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

Jul 15 – 22

ﺩ.ﺇ409 per night
Guest favorite

Guesthouse in Chipley

4.96 out of 5 average rating, 178 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.

Aug 11 – 18

ﺩ.ﺇ471 per night
Guest favorite

Guest suite in Enterprise

4.98 out of 5 average rating, 458 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;

Apr 18 – 25

ﺩ.ﺇ223 per night

Popular amenities for Chipley vacation rentals

Other great vacation rentals in Chipley

Guest favorite

Cottage in Marianna

5.0 out of 5 average rating, 82 reviews

Quiet, cozy 1 bdrm cottage near Caverns & Bear Paw

Jul 16 – 23

ﺩ.ﺇ460 per night
Guest favorite

Home in Marianna

4.92 out of 5 average rating, 39 reviews

"The Marianna"- Cute Cottage in Historic Downtown

Sep 24 – Oct 1

ﺩ.ﺇ466 per night
Guest favorite

Cottage in Vernon

5.0 out of 5 average rating, 40 reviews

Cozy cottage near springs & beach

Sep 5 – 12

ﺩ.ﺇ462 per night
Guest favorite

Cottage in Chipley

5.0 out of 5 average rating, 20 reviews

The Fifth Promise - A Crystal Lake Retreat

May 13 – 20

ﺩ.ﺇ1,141 per night
Guest favorite

Home in Chipley

4.95 out of 5 average rating, 42 reviews

Latitude Adjustment

Aug 15 – 22

ﺩ.ﺇ586 per night
Guest favorite

Cottage in Cottonwood

4.96 out of 5 average rating, 25 reviews

Cozy Cottage in the Pines

Nov 15 – 22

ﺩ.ﺇ382 per night
Guest favorite

Farm stay in Chipley

4.88 out of 5 average rating, 50 reviews

Nice Cozy Rural RV

Jun 9 – 16

ﺩ.ﺇ351 per night
Guest favorite

Home in Vernon

4.91 out of 5 average rating, 98 reviews

Remodeled lakefront home with lake access.

Oct 2 – 9

ﺩ.ﺇ683 per night
Superhost

Barn in Slocomb

4.89 out of 5 average rating, 9 reviews

Zeke’s House: Bed & Barn Bliss

Oct 20 – 27

ﺩ.ﺇ261 per night
Superhost

Home in Chipley

5.0 out of 5 average rating, 7 reviews

2 bedroom house to yourself, in town- but private

May 16 – 23

ﺩ.ﺇ647 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.

May 30 – Jun 6

ﺩ.ﺇ388 per night
Guest favorite

Home in Altha

4.99 out of 5 average rating, 79 reviews

Wandering Waters Cabin

Aug 17 – 24

ﺩ.ﺇ572 per night

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

180 reviews

Nightly prices starting at

ﺩ.ﺇ184 before taxes and fees

Destinations to explore

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  2. United States
  3. Florida
  4. Washington County
  5. Chipley