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.
The price is CA $155
CA $230 total
includes taxes & fees
Jun 14 - Jun 15
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, (4 reviews)
"Easy check in. Breakfast was delicious. Quite county setting. "
United States
Deborah H.
The price is CA $168
CA $332 total
includes taxes & fees
Jun 1 - Jun 2
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
The price is CA $156
CA $253 total
includes taxes & fees
Jun 2 - Jun 3
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, (27 reviews)
"Amazing place"
United States
Alex R.
The price is CA $207
CA $360 total
includes taxes & fees
Jun 2 - Jun 3
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

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
The price is CA $131
CA $258 total
includes taxes & fees
Jun 8 - Jun 9
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, (182 reviews)
"Nice view. Good communication with escala host"
United States
Lori V.
The price is CA $135
CA $791 total
includes taxes & fees
Jun 1 - Jun 2
Bring your Pet! Amazing 3rd floor unit! Outstanding Views and Amenities!

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 CA $149
CA $676 total
includes taxes & fees
Jun 7 - Jun 8
3BR Canal-front Home w/ Wifi & Boat Dock

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.
The price is CA $124
CA $408 total
includes taxes & fees
Jun 2 - Jun 3
Origin 0538- Studio - Breath Taking Gulf Views

Splash Beach Resort by Panhandle Getaways

Splash Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
7.4 out of 10, Good, (210 reviews)
"View was excellent. "
United States
Ronald
The price is CA $167
CA $735 total
includes taxes & fees
Jun 2 - Jun 3
Splash Beach Resort by Panhandle Getaways

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, (252 reviews)
"Great stay while in town for baseball. "
United States
Jessica T.
The price is CA $192
CA $504 total
includes taxes & fees
Jun 7 - Jun 8
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

Ocean-front Master Bedroom with Spectacular View!!!

Ocean-front Master Bedroom with Spectacular View!!!
Panama City Beach
9.4 out of 10, Exceptional, (146 reviews)
"Excellent stay, great view. "
United States
Richard T.
The price is CA $163
CA $463 total
includes taxes & fees
Jun 1 - Jun 2
Ocean-front Master Bedroom with Spectacular View!!!

Origin At Seahaven

Origin At Seahaven
3.5 star property
Panama City Beach
7.0 out of 10, Good, (2,186 reviews)
"It was a nice stay. Room was really nice. "
United States
Paul
The price is CA $145
CA $375 total
includes taxes & fees
Jun 1 - Jun 2
Origin At Seahaven

Fountain of Youth Edgewater Villa 955-Tranquil Pond Views! Free Beach Tram! Remodeled Condo!

Fountain of Youth Edgewater Villa 955-Tranquil Pond Views! Free Beach Tram! Remodeled Condo!
Panama City Beach
10.0 out of 10, Exceptional, (10 reviews)
"Great place"
United States
Benjamin C.
The price is CA $256
CA $860 total
includes taxes & fees
Jun 1 - Jun 2
Fountain of Youth Edgewater Villa 955-Tranquil Pond Views! Free Beach Tram! Remodeled Condo!

Beach getaway just 100 yards from the beach.

Beach getaway just 100 yards from the beach.
Laguna Beach
10.0 out of 10, Exceptional, (100 reviews)
"Would stay again, nice place"
United States
Leigh
The price is CA $234
CA $532 total
includes taxes & fees
Jun 6 - Jun 7
Beach getaway just 100 yards from the beach.

Lovely Townhouse Steps From Beach w/Free WiFi, Breathtaking Views, & Central AC

Lovely Townhouse Steps From Beach w/Free WiFi, Breathtaking Views, & Central AC
Sunnyside
9.6 out of 10, Exceptional, (26 reviews)
"Perfect location for a family vacation! "
United States
Lorrie G.
The price is CA $296
CA $721 total
includes taxes & fees
Jun 28 - Jun 29
Lovely Townhouse Steps From Beach w/Free WiFi, Breathtaking Views, & Central AC

Dog-Friendly Poolside Retreat Near the Beach with Room for the Family

Dog-Friendly Poolside Retreat Near the Beach with Room for the Family
Panama City Beach
9.4 out of 10, Exceptional, (33 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.
The price is CA $243
CA $916 total
includes taxes & fees
Jun 1 - Jun 2
Dog-Friendly Poolside Retreat Near the Beach with Room for the Family

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
The price is CA $149
CA $588 total
includes taxes & fees
Jun 3 - Jun 4
Beautiful PCB Townhome: Balcony & Resort Amenities

Magnificent View of the Gulf of America Near Pier Park. BOOK YOUR VACATION NOW!

Magnificent View of the Gulf of America Near Pier Park. BOOK YOUR VACATION NOW!
Panama City Beach
9.8 out of 10, Exceptional, (133 reviews)
"Very nice smaller condo right near the beach, convenient to everything."
United States
David H.
The price is CA $222
CA $677 total
includes taxes & fees
Jun 1 - Jun 2
Magnificent View of the Gulf of America Near Pier Park. BOOK YOUR VACATION NOW!

Grand Panama Beach Resort by Panhandle Getaways

Grand Panama Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
8.4 out of 10, Very good, (106 reviews)
"Our room had a beach front view. The room was very clean and spacious. The bed slept great! We would definitely stay again. "
United States
Leslie
The price is CA $330
CA $1,117 total
includes taxes & fees
Jun 6 - Jun 7
Grand Panama Beach Resort by Panhandle Getaways

Beachfront!! Free Beach Chairs!! Over 297 Five Star Reviews!

Beachfront!! Free Beach Chairs!! Over 297 Five Star Reviews!
Miramar Beach
10.0 out of 10, Exceptional, (298 reviews)
"Very nice condo right on Panama City Beach. Property was clean and nice and having two pool options was a real plus. The beach was beautiful and not too crowded at any point of the trip. I would recommend this rental for sure."
United States
Tom
The price is CA $233
CA $689 total
includes taxes & fees
Jun 1 - Jun 2
Beachfront!! Free Beach Chairs!! Over 297 Five Star Reviews!
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chipley. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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: Visitors like this Chipley vacation home rental. It 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.