We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals in Chipley

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chipley

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

0 of 0 items showing

1 of 3 pages

Cottage in Marianna

5 out of 5 average rating, 116 reviews

Chipola Woods quiet & cozy near Caverns, Bear Paw

No cleaning fees! Our one and only peaceful, quiet golf cart friendly location 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 including HBO Max & Prime. Queen pull out sofa w/mattress topper for extra comfort (on request)

Guesthouse in Chipley

4.96 out of 5 average rating, 273 reviews

Guesthouse & Heated 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 suite in Enterprise

4.98 out of 5 average rating, 524 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;

Cottage in Dothan

4.96 out of 5 average rating, 247 reviews

The Oak Nest Garden District

Our cozy cottage home is 900 square feet and it is located behind our home in the beautiful garden district-a quiet, peaceful neighborhood. This adorable cottage has a full, spacious kitchen(sink, refrigerator,stove/oven, microwave, dishwasher basic cooking needs),living room, dining room, bar seating,bedroom with a queen-sized bed, walk-in closet, and stack unit washer/dryer. We are convenient to ACOM and 30 minutes to Fort Rucker. There are 2 nearby parks as well as hospitals.

Home in Donalsonville

4.98 out of 5 average rating, 160 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.

Cottage in Dothan

4.99 out of 5 average rating, 171 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.

Rental unit in Ponce de Leon

4.92 out of 5 average rating, 107 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 springs state park. Takes about 10-15 minutes to get to Vortex Springs or Morrison Springs. We are only 45 minutes to the beautiful white sand beaches in Panama City beach. Make yourself at home and rest and reset in a country atmosphere. We look forward to hosting you. NO CLEANING FEE. This Airbnb is behind our home, where we live.

Rental unit in Dothan

4.92 out of 5 average rating, 400 reviews

Claire’s Cottage with privacy gate

Everything you need in a quaint, modern space located on 7 secluded acres with a privacy gate only minutes from the Ross Clark Circle and downtown, Wi-Fi, Smart TV with YouTube TV subscription included (over 70 channels), brand new fridge, spacious rooms. Washer and dryer available. We allow pets on a case by case basis and charge a one time $10 fee per pet upon guests arrival. We also offer EV level 2 charging (40 amp) for a flat $10 fee.

Cabin in Opp

4.96 out of 5 average rating, 249 reviews

Boothe Pond Cabin on East Fork Creek

Beautiful pond cabin on a secluded dirt road along the popular route to 30A beaches. Fishing available from shore and the property includes a small boat launch, fire pit, porch swing, rocking chairs, grill, and picnic tables. A full kitchen and cabin amenities in a picturesque setting. This is a great place for family to get away or to stop by and rest while traveling south the the beaches.

Tiny home in Slocomb

4.98 out of 5 average rating, 129 reviews

Comfortable Tiny House In Wicksburg

Comfortable tiny home in Wicksburg, Alabama offers a loft with a queen size bed. The downstairs has another sleeping area that includes a twin size sleeper sofa. The spacious kitchen has new appliances. There is a scenic view for a peaceful stay, but only about 1 hours drive from places like Panama City Beach Florida. Also, Dothan is 14 miles and Ft Rucker is 12 miles away.

Home in Altha

4.99 out of 5 average rating, 107 reviews

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.

Cabin in Marianna

4.92 out of 5 average rating, 183 reviews

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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Chipley vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Chipley

Barn in Slocomb

4.92 out of 5 average rating, 39 reviews

Zeke’s House: Bed & Barn Bliss

Cabin in Sneads

5 out of 5 average rating, 35 reviews

LouLouBell's Getaway

Home in Dothan

4.95 out of 5 average rating, 59 reviews

Cozy Cottage

Farm stay in Slocomb

4.92 out of 5 average rating, 38 reviews

Quiet 2 bedroom home in a country setting.

Home in Geneva

4.92 out of 5 average rating, 25 reviews

Haven of Rest

Home in Chipley

5 out of 5 average rating, 13 reviews

Making Memories Lucas Lake

Cabin in Panama City

4.93 out of 5 average rating, 80 reviews

Cabin on Private Beach with Tiki Bar & Cabana

Home in Bonifay

4.89 out of 5 average rating, 18 reviews

Entire Home - Peaceful Pines - Near Springs

Frequently Asked Questions

How much does it cost to stay in house rentals in Chipley?
Experience the best of Chipley with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Chipley?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Chipley have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Chipley. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chipley have free parking?
Absolutely! We offer over 10 house rentals with free parking in Chipley. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore