Chipley Vacation Rentals

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Our top choices for Chipley vacation rentals

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.
$153 nightly
The price is $166
May 10 - May 11
Total with taxes and fees
Cozy Lakefront Airstream

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, (3 reviews)
"Easy check in. Breakfast was delicious. Quite county setting. "
United States
Deborah H.
$215 nightly
The price is $235
May 8 - May 9
Total with taxes and fees
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

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
$163 nightly
The price is $178
May 11 - May 12
Total with taxes and fees
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

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

Charming waterfront barndominium on the beautiful spring-fed Chipola River.
Altha
9.6 out of 10, Exceptional, (25 reviews)
"Amazing place"
United States
Alex R.
$241 nightly
The price is $257
May 8 - May 9
Total with taxes and fees
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

Private Cozy bedroom with on suite living room

Private Cozy bedroom with on suite living room
Panama City
9.8 out of 10, Exceptional, (29 reviews)
"Overall great experience and would definitely stay again😊"
United States
Mary B.
$130 nightly
The price is $138
May 8 - May 9
Total with taxes and fees
Private Cozy bedroom with on suite living room

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
$175 nightly
The price is $186
May 9 - May 10
Total with taxes and fees
Pelican's Nest - The Hideaway in Panama City

Bring your Pet! Amazing 3rd floor unit! Outstanding Views and Amenities!

Bring your Pet! Amazing 3rd floor unit! Outstanding Views and Amenities!
Panama City Beach
9.4 out of 10, Exceptional, (181 reviews)
"Nice view. Good communication with escala host"
United States
Lori V.
$484 nightly
The price is $540
May 11 - May 12
Total with taxes and fees
Bring your Pet! Amazing 3rd floor unit! Outstanding Views and Amenities!

#101 Somerset PETS WELCOMED

#101 Somerset PETS WELCOMED
Bahama Beach
8.4 out of 10, Very Good, (21 reviews)
"Very clean and a great price for the location!"
United States
Matthew
$246 nightly
The price is $274
May 10 - May 11
Total with taxes and fees
#101 Somerset PETS WELCOMED

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

3BR Canal-front Home w/ Wifi & Boat Dock
3.0 star property
Bayside Park
$450 nightly
The price is $479
May 17 - May 18
Total with taxes and fees
3BR Canal-front Home w/ Wifi & Boat Dock

🐾🏖️Summer Deals!! Free Activities for Summer ! DOG Friendly🏖️🐾

🐾🏖️Summer Deals!! Free Activities for Summer ! DOG Friendly🏖️🐾
Panama City Beach
9.4 out of 10, Exceptional, (32 reviews)
"The location was great. The access to the pool was awesome. Everything was in walking distance. The couch and chairs needs to be replaced and it had dog hair everywhere. "
United States
Bianca S.
$552 nightly
The price is $600
May 8 - May 9
Total with taxes and fees
🐾🏖️Summer Deals!! Free Activities for Summer ! DOG Friendly🏖️🐾

Polynesian #104 Ground Level

Polynesian #104 Ground Level
Panama City Beach
8.8 out of 10, Excellent, (56 reviews)
"Our stay was exactly what we expected. A nice place to stay close to everything yet far enough away for the beech to no be too crowded. "
United States
heather h.
$208 nightly
The price is $232
May 10 - May 11
Total with taxes and fees
Polynesian #104 Ground Level

gulf view! only 30 steps to the HEATED pool and hot tub!!

gulf view! only 30 steps to the HEATED pool and hot tub!!
Panama City Beach
10.0 out of 10, Exceptional, (66 reviews)
"Perfect week away for my wife and i.....pool and hot.tub are steps away !!!"
United States
JEFF K.
$310 nightly
The price is $346
May 11 - May 12
Total with taxes and fees
gulf view! only 30 steps to the HEATED pool and hot tub!!

Pier Serenity **Beachfront Corner End Balcony** Sleeps 2

Pier Serenity **Beachfront Corner End Balcony** Sleeps 2
Panama City Beach
9.4 out of 10, Exceptional, (119 reviews)
"The views were Amazing ..My quate little condo was just the right size for myself n my guests .. definitely will recommend for a little getaway for 2"
United States
Deanna
$213 nightly
The price is $224
May 26 - May 27
Total with taxes and fees
Pier Serenity **Beachfront Corner End Balcony** Sleeps 2

Origin 0538- Studio - Breath Taking Gulf Views

Origin 0538- Studio - Breath Taking Gulf Views
Panama City Beach
9.2 out of 10, Wonderful, (32 reviews)
"great place to stay, will definately be staying there again"
United States
John L.
$256 nightly
The price is $286
May 10 - May 11
Total with taxes and fees
Origin 0538- Studio - Breath Taking Gulf Views

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, (176 reviews)
"Great stay"
United States
John
$532 nightly
The price is $602
May 12 - May 13
Total with taxes and fees
Calypso Beach Resort by Panhandle Getaways

Book Now!! Balcony is right on the beachside. Great view of the Emerald Water!

Book Now!! Balcony is right on the beachside. Great view of the Emerald Water!
Panama City Beach
9.8 out of 10, Exceptional, (264 reviews)
"Great stay!"
United States
Kathy E.
$287 nightly
The price is $320
May 12 - May 13
Total with taxes and fees
Book Now!! Balcony is right on the beachside. Great view of the Emerald Water!

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, (248 reviews)
"Great stay while in town for baseball. "
United States
Jessica T.
$273 nightly
The price is $304
May 11 - May 12
Total with taxes and fees
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

Calypso Tower 3 by Panhandle Getaways

Calypso Tower 3 by Panhandle Getaways
3.5 star property
Panama City Beach
8.8 out of 10, Excellent, (22 reviews)
"excellent location - very clean and fun pool area "
United States
Dave
$536 nightly
The price is $606
May 9 - May 10
Total with taxes and fees
Calypso Tower 3 by Panhandle Getaways

Beautiful PCB Townhome: Balcony & Resort Amenities

Beautiful PCB Townhome: Balcony & Resort Amenities
4.0 star property
Panama City Beach
10.0 out of 10, Exceptional, (2 reviews)
"Yes, everything was good and I like how the places to shop and eat were also close by."
United States
Ketline
$408 nightly
The price is $458
Jun 3 - Jun 4
Total with taxes and fees
Beautiful PCB Townhome: Balcony & Resort Amenities

Studio Home Just a Minute Walk from the Beach! Book before gone!

Studio Home Just a Minute Walk from the Beach! Book before gone!
Panama City Beach
9.2 out of 10, Wonderful, (19 reviews)
"Just a nice place to stay while in Pcb."
United States
Benjamin P.
$295 nightly
The price is $329
May 26 - May 27
Total with taxes and fees
Studio Home Just a Minute Walk from the Beach! Book before gone!
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.
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Top Chipley Hotel Reviews

Find out more about Chipley

Everything you need to know about Chipley vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chipley vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chipley vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chipley vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chipley. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chipley in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $287 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chipley rentals

At Expedia, we put the best Chipley vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chipley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chipley vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chipley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

❃ Walkable to Food & Fun ❃ Beach-Front Pool ❃ Canal-Side Home ❃ No Pet Fee: You might want to consider this vacation rental near Chipley, which is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Chipley?

Choose from 6 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. In the larger area, you’ll find Pal's Park and Moss Hill Methodist Church.

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.