A waterfall cascading over a rocky cliff surrounded by lush green ferns and foliage.

Chipley Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Chipley vacation rentals

Indoor pool, a heated pool

Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
Chipley
10.0 out of 10, Exceptional, (5 reviews)
"Easy check in. Breakfast was delicious. Quite county setting. "
United States
Deborah H.
The price is ￥18,867
￥37,208 total
includes taxes & fees
Jul 23 - Jul 24
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
Property grounds

Cozy Lakefront Airstream

Cozy Lakefront Airstream
Chipley
9.8 out of 10, Exceptional, (14 reviews)
"We loved the property, enjoyed all the amenities and relaxed comfortably."
United States
Lesley H.
The price is ￥20,300
￥29,269 total
includes taxes & fees
Aug 19 - Aug 20
Cozy Lakefront Airstream
Pool

Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery
Chipley
The price is ￥18,689
￥30,187 total
includes taxes & fees
Jul 22 - Jul 23
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery
Condo, 3 Bedrooms, Sea View (2302W) | View from room

Calypso Beach Resort by Panhandle Getaways

Calypso Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
8.8 out of 10, Excellent, (183 reviews)
"We enjoyed our stay. The condo was a goos size and had a nice layout! Beautiful view of the gulf without all the noise!"
United States
Jacob
The price is ￥26,327
￥106,079 total
includes taxes & fees
Aug 21 - Aug 22
Calypso Beach Resort by Panhandle Getaways
2 Bedroom Gulf View | Living area | 50-inch flat-screen TV with cable channels, TV

Origin At Seahaven

Origin At Seahaven
3.5 star property
Panama City Beach
7.0 out of 10, Good, (2,194 reviews)
"Super nice!! Family friendly! Great location!"
United States
Kennedy
The price is ￥15,103
￥41,757 total
includes taxes & fees
Aug 16 - Aug 17
Origin At Seahaven
Property grounds

Charming waterfront barndominium on the beautiful spring-fed Chipola River.

Charming waterfront barndominium on the beautiful spring-fed Chipola River.
Altha
9.8 out of 10, Exceptional, (31 reviews)
The price is ￥24,360
￥42,408 total
includes taxes & fees
Jul 23 - Jul 24
Charming waterfront barndominium on the beautiful spring-fed Chipola River.
Condo, 3 Bedrooms, Ocean View (1708E) | View from room

Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
3.5 star property
Panama City Beach
10.0 out of 10, Exceptional, (1 review)
"Great place, we really enjoyed our trip and stay!"
United States
Brent
The price is ￥23,557
￥104,040 total
includes taxes & fees
Aug 13 - Aug 14
Calypso Beach Resort Tower 1
On the beach, white sand

Calypso Tower 3 by Panhandle Getaways

Calypso Tower 3 by Panhandle Getaways
3.5 star property
Panama City Beach
9.0 out of 10, Wonderful, (30 reviews)
"excellent location - very clean and fun pool area "
United States
Dave
The price is ￥22,068
￥108,062 total
includes taxes & fees
Aug 2 - Aug 3
Calypso Tower 3 by Panhandle Getaways
Condo, 2 Bedrooms, Balcony, Ocean View (602 E) | Balcony view

Calypso Resort and Towers by Book That Condo

Calypso Resort and Towers by Book That Condo
4.0 star property
Panama City Beach
9.4 out of 10, Exceptional, (8 reviews)
"Perfect location"
United States
Weylin
The price is ￥62,818
￥145,629 total
includes taxes & fees
Jul 29 - Jul 30
Calypso Resort and Towers by Book That Condo
House | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

Beach House - The Sanderling by PHG

Beach House - The Sanderling by PHG
4.0 star property
Sunnyside
Beach House - The Sanderling by PHG
Sun loungers

Private Pool, Walk to Beach 🏖️, Bright Sun Room, Quiet West End

Private Pool, Walk to Beach 🏖️, Bright Sun Room, Quiet West End
Sunnyside
9.6 out of 10, Exceptional, (128 reviews)
"Nice clean house close to the beach. "
United States
Eric M.
Private Pool, Walk to Beach 🏖️, Bright Sun Room, Quiet West End
Beach nearby

Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!

Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!
Laguna Beach
8.8 out of 10, Excellent, (23 reviews)
"Great place to stay especially if you have your puppy. It was a really great location "
United States
Christina
The price is ￥16,088
￥60,908 total
includes taxes & fees
Jul 26 - Jul 27
Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!
Beach nearby

Family-friendly Beach Retreat w/ Pools, Hot Tub & Tennis

Family-friendly Beach Retreat w/ Pools, Hot Tub & Tennis
3.5 star property
Panama City Beach
The price is ￥24,783
￥107,262 total
includes taxes & fees
Aug 9 - Aug 10
Family-friendly Beach Retreat w/ Pools, Hot Tub & Tennis
View from property

Tidewater Beach Resort by Panhandle Getaways

Tidewater Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
7.4 out of 10, Good, (188 reviews)
"My family and I absolutely loved it! The service was excellent, and the staff were very kind, friendly, and always helpful. From the moment you walk into the apartment, you can immediately notice how clean and well-organized everything is. The smell of cleanliness is very pleasant. The towels, bed linens, and the entire place were spotless and very well maintained. We stayed in apartment 310 on the 30th floor, and the view was absolutely spectacular. The location is also perfect—very central...
United States
Claudia
The price is ￥23,629
￥93,414 total
includes taxes & fees
Aug 9 - Aug 10
Tidewater Beach Resort by Panhandle Getaways
Outdoor dining

Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!
Panama City Beach
9.4 out of 10, Exceptional, (257 reviews)
"Great stay while in town for baseball. "
United States
Jessica T.
The price is ￥17,551
￥53,441 total
includes taxes & fees
Aug 2 - Aug 3
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!
TV

Gulf Front~Balcony~Fitness Room~2BR Tropic Winds 1104

Gulf Front~Balcony~Fitness Room~2BR Tropic Winds 1104
Panama City Beach
9.2 out of 10, Wonderful, (108 reviews)
"Unbelievable view, loved sitting on the balcony watching the waves and dolphins swim by. Quiet area of the beach which was perfect for us. Bed was comfortable, heat and a/c both worked well (there was a cold snap for part of our trip). Elevators were always available. The other reviews are real as far as parking- I wouldn’t want to try to park a large truck or SUV in the garage. We will definitely stay again next time we are in PCB. "
United States
Kathleen G.
Gulf Front~Balcony~Fitness Room~2BR Tropic Winds 1104
House (3 Bedrooms) | Interior

3BR Canal-front Home w/ Wifi & Boat Dock

3BR Canal-front Home w/ Wifi & Boat Dock
3.0 star property
Bayside Park
The price is ￥20,462
￥78,226 total
includes taxes & fees
Aug 9 - Aug 10
3BR Canal-front Home w/ Wifi & Boat Dock
Property grounds

On the Beach, Best Resort in PCB,Family Friendly,8 Floor, Beach Chairs Included

On the Beach, Best Resort in PCB,Family Friendly,8 Floor, Beach Chairs Included
Panama City Beach
9.2 out of 10, Wonderful, (326 reviews)
"Condo was such a fun experience for our family! Great location and easy access to everything we wanted to do! "
United States
Jennifer F.
The price is ￥30,714
￥67,197 total
includes taxes & fees
Jul 23 - Jul 24
On the Beach, Best Resort in PCB,Family Friendly,8 Floor, Beach Chairs Included
Condo, 2 Bedrooms (908-1) | View from room

Grand Panama Beach Resort by Book That Condo

Grand Panama Beach Resort by Book That Condo
4.0 star property
Panama City Beach
9.0 out of 10, Wonderful, (44 reviews)
"The cleanest place we have ever stayed. The condo was perfect. And the view from the balcony was breath taking."
United States
Heather
The price is ￥35,348
￥101,539 total
includes taxes & fees
Aug 15 - Aug 16
Grand Panama Beach Resort by Book That Condo
Exterior

Pelican's Nest - The Hideaway in Panama City

Pelican's Nest - The Hideaway in Panama City
Panama City
9.8 out of 10, Exceptional, (16 reviews)
"Great!"
United States
Richard
Pelican's Nest - The Hideaway in Panama City
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chipley Hotel Reviews

Radisson Beachfront Hotel - Panama City Beach

Radisson Beachfront Hotel - Panama City Beach

10/10 Excellent
"Stayed here for 3 nights with my young daughter and husband. It was pleasantly surprised by how great the location was and spacious the rooms were. Property is kept clean, the rooms were clean and located right on the beach. I have to say I slept well the beds seem to have been new and plush. The amenities need some up keep for example showers near pool need to be serviced button was broken and water pressure was off. Pool was nice and chairs seemed new. Pool definitely needs some TLC in terms of cleaniness (water), debris (in pool) and upkeep. Hot tub was very warm but the problem was it was not cleaned regularly tons of bugs and debris inside. Beach was amazing loved it and shore area was very clean and well kept. Overall experience was good and would recommend to friends."
Amanda 3-night trip
Posted 11 hours ago
Radisson Beachfront Hotel - Panama City Beach

Find out more about Chipley

Search for holiday rentals in Chipley on Expedia! You can easily find your home rentals, villas, holiday apartments in Chipley using one of the methods below:

  • View our selection of featured holiday rentals in Chipley
  • Use the map to find apartments and other holiday homes in the Chipley neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chipley while they last

Look no further and take a look at our great range of rental properties in Chipley!

Frequently asked questions

Can I find vacation rentals in Chipley?

Yes, there are vacation rentals close to popular points of interest in Chipley, or you can go with a secluded option if you'd like a relaxing place to stay. Chipley is known for its churches and lake views. Make sure you have time to check out the forests while you're in the area.

What's the top vacation rental that Chipley has to offer?

Elizabeth's Memories - Beach Front: Visitors like this Chipley vacation home rental. It is located on the beach and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, an oven, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Chipley?

Choose from 7 Expedia vacation rentals in Chipley for a memorable vacation.

What can I see and do in Chipley?

Falling Waters State Park and Lucas Lake are a couple of lovely local spots to get outside and enjoy nature. Pal's Park and River Lake are other places to visit while you're in town.

What are vacation rentals like in Chipley?

Vacation rentals are private accommodations you can book for a couple days or more in Chipley. Vacation rentals feature amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for families.