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Vacation rentals in Chipley

Vacation rentals in Chipley

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chipley

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

  • Hartford Art Studio and Loft
    SUPERHOSTFarm stay · 2 guests · 1 bed · 1 bathroom
    Hartford Art Studio and Loft

    This treasure is a stand alone art studio with a loft surrounded by beautiful lawn and gardens. There are agricultural fields on three sides and a scenic lake in the rear. The artist, Beverly Mayfield, is now deceased, but has filled the studio with masterful paintings.

    What guests are saying:

    “Randy's place is even more beautiful than the pictures show. You will love the lush garden view from the picture window while enjoying your morning coffee or relaxing while watching the sunset after dinner. Both Dothan and Enterprise are close by and offer many things to do. The botanical gardens are worth seeing and we really enjoyed the Folklore Brewery outside of Dothan. The studio/loft was very comfortable and cozy and Beverly's artwork is truly mesmerizing. Randy is a great host.”

  • Live Simply Entire Tiny House/Shed conversion
    SUPERHOSTTiny house · 3 guests · 2 beds · 1 bathroom
    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. A comfy sofa to relax and have some popcorn while watching your Netflix, Prime or Hulu favorites. Also available for longer stays, just ask! Check out our campground otw to the beach! Enjoy!

    What guests are saying:

    “This is such a remarkable place. There is plenty of breathing space. The decor feels homey with a nice touch of decorative lights outlining the room. The place smelled absolutely delightful upon entering and the decorative lights were on and along with candles. It felt like such a warm welcome when we arrived from a long 4-hour drive. Everything that we needed was in the room, comfy bed, quiet neighborhood, and a perfect place to relax and de-stress from the day.”

  • Artist Cottage
    SUPERHOSTEntire cottage · 2 guests · 1 bed · 1 bathroom
    Artist Cottage

    Our cozy "Artist Cottage" will accommodate two adults. It is nestled in the woods and provides peace, quiet and the sounds of nature. Disconnect from the TV and internet for a stress free visit. A short distance from Diving Springs and Kayaking. Close to Seacrest Wolf Preserve and area State Parks. Travel one exit west on interstate I10 for restaurant's and groceries. Thank you for understanding that children and pets are not accepted.

    What guests are saying:

    “I typically get hotels but this was the perfect place for a weekend vacation. Clean and has literally everything you need to have a weekend with your significant other. Close by to the springs. Easy access with plenty of amenities. Objectively 5/5 need to come back again. If you’re looking for a place to take your girlfriend she will love this place as it’s not crowded and the perfect atmosphere”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Chipley holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chipley

Cozy Guesthouse nestled on 3 acres.
SUPERHOSTEntire guest house
Cozy Guesthouse nestled on 3 acres.
Price:₹3,757 / night
A beautiful place
SUPERHOSTEntire cabin
A beautiful place
Price:₹11,161 / night
Ashton Place Apartment 1
SUPERHOSTEntire flat
Ashton Place Apartment 1
Price:₹3,720 / night
The Farm House
SUPERHOSTEntire house
The Farm House
Price:₹11,161 / night
A Lovely Log Cabin in the Woods  New Hope Florida
Entire cabin
A Lovely Log Cabin in the Woods New Hope Florida
Price:₹8,185 / night
Dothan's Cottage
SUPERHOSTEntire cottage
Dothan's Cottage
Price:₹7,106 / night
Latitude Adjustment
SUPERHOSTEntire house
Latitude Adjustment
Price:₹11,161 / night
★ Clean Air and Surfaces ★ Private Nature Retreat
Entire house
★ Clean Air and Surfaces ★ Private Nature Retreat
Price:₹5,667 / night
The Sleeping Porch - The Hinson House
SUPERHOSTPrivate room
The Sleeping Porch - The Hinson House
Price:₹8,358 / night
The Cabin
SUPERHOSTEntire house
The Cabin
Price:₹5,593 / night
Choctawhatchee river at its finest! Sleep up to 8
Campervan/Motorhome
Choctawhatchee river at its finest! Sleep up to 8
Price:₹6,696 / night
The Studio
Entire guest suite
The Studio
Price:₹3,720 / night
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