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Chipley Vacation Rentals

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Our top choices for Chipley vacation rentals

1. 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
10.0 out of 10, Exceptional, (1 review)
"Very nice place to stay. Host was very helpful and accommodating. Enjoyed being way out in the country."
United States
Gwen S.
The price is CA $119
CA $203 total
includes taxes & fees
Nov 17 - Nov 18
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

2. The Cozy Farmhouse Retreat

The Cozy Farmhouse Retreat
Chipley
The price is CA $363
CA $824 total
includes taxes & fees
Dec 6 - Dec 7
The Cozy Farmhouse Retreat

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

Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
Chipley
9.6 out of 10, Exceptional, (7 reviews)
"Great place to stay!"
United States
Carrie P.
The price is CA $170
CA $321 total
includes taxes & fees
Nov 7 - Nov 8
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

4. 4-bedroom Lake House 45 Minutes from the Beach!

4-bedroom Lake House 45 Minutes from the Beach!
Chipley
10.0 out of 10, Exceptional, (10 reviews)
"This house served as a great getaway for our family reunion. The views of the lake were beautiful. The lake water was also clear, and we enjoyed fishing off the dock during our stay. The host responded quickly to messages."
United States
Jennifer M.
The price is CA $430
CA $928 total
includes taxes & fees
Nov 7 - Nov 8
4-bedroom Lake House 45 Minutes from the Beach!

5. Charming In-town Bungalow

Charming In-town Bungalow
Marianna
10.0 out of 10, Exceptional, (13 reviews)
"The home was so beautiful and cozy. The kitchen was well equipped and the home was impeccably decorated. The owners texted often to make sure we were comfortable and enjoying our stay."
United States
Jennifer
The price is CA $138
CA $439 total
includes taxes & fees
Nov 9 - Nov 10
Charming In-town Bungalow

6. 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, (36 reviews)
"Amazing place"
United States
Alex R.
The price is CA $224
CA $382 total
includes taxes & fees
Nov 8 - Nov 9
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

7. Private - Waterfront Cottage - Panama City, FL

Private - Waterfront Cottage - Panama City, FL
Panama City
10.0 out of 10, Exceptional, (24 reviews)
"Doedy seems like a best friend type of person, who goes out of her way to connect and create a comfortable stay. The property is super cute and we loved the quietness behind another property location. 10 stars, hoping to be able to stay again soon."
United States
celeste n.
The price is CA $182
CA $434 total
includes taxes & fees
Nov 9 - Nov 10
Private - Waterfront Cottage - Panama City, FL

8. Origin At Seahaven

Origin At Seahaven
3.5 star property
Panama City Beach
7.0 out of 10, Good, (2,223 reviews)
"Great place to stay! Room was clean and spacious! Will stay again."
United States
Gerald
The price is CA $89
CA $308 total
includes taxes & fees
Nov 12 - Nov 13
Origin At Seahaven

9. Calypso Tower 3 by Panhandle Getaways

Calypso Tower 3 by Panhandle Getaways
3.5 star property
Panama City Beach
9.2 out of 10, Wonderful, (42 reviews)
"The property was very clean and in an excellent location . We weren’t on the beach , but we had a great view of the ocean and the pools I would highly recommend"
United States
Thomas
The price is CA $169
CA $832 total
includes taxes & fees
Nov 8 - Nov 9
Calypso Tower 3 by Panhandle Getaways

10. Polynesian #104 Ground Level

Polynesian #104 Ground Level
Panama City Beach
8.4 out of 10, Very good, (68 reviews)
"Great location and view! "
United States
kerri m.
The price is CA $70
CA $270 total
includes taxes & fees
Nov 28 - Nov 29
Polynesian #104 Ground Level

11. Calypso Beach Resort Tower 2 by Panhandle Getaways

Calypso Beach Resort Tower 2 by Panhandle Getaways
3.5 star property
Panama City Beach
8.8 out of 10, Excellent, (198 reviews)
"The room and view were absolutely amazing!"
United States
Brittany
The price is CA $205
CA $888 total
includes taxes & fees
Nov 8 - Nov 9
Calypso Beach Resort Tower 2 by Panhandle Getaways

12. Octa Collection on Front Beach

Octa Collection on Front Beach
4.5 star property
Long Beach
The price is CA $182
CA $467 total
includes taxes & fees
Nov 18 - Nov 19
Octa Collection on Front Beach

13. 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, (32 reviews)
"Overall good place to stay and very close to the beach and other activities"
United States
TsTzero5
The price is CA $124
CA $514 total
includes taxes & fees
Nov 7 - Nov 8
Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!

14. Splash Resort 605E•Best in PCB•Beach Chairs•Crib•Fireplace

Splash Resort 605E•Best in PCB•Beach Chairs•Crib•Fireplace
Panama City Beach
9.8 out of 10, Exceptional, (49 reviews)
"Great place to bring the kids to enjoy the beach."
United States
Eloise S.
The price is CA $129
CA $541 total
includes taxes & fees
Dec 1 - Dec 2
Splash Resort 605E•Best in PCB•Beach Chairs•Crib•Fireplace

15. 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 $111
CA $413 total
includes taxes & fees
Nov 17 - Nov 18
Origin 0538- Studio - Breath Taking Gulf Views

16. Coastal Breeze Perfect Family Getaway/ Sleep 9

Coastal Breeze Perfect Family Getaway/ Sleep 9
Laguna Beach
9.4 out of 10, Exceptional, (79 reviews)
"Property was easy to find. Very spacious. Plenty of room for our family. Great location in proximity to the beach, food, and shopping."
United States
Brittany K.
The price is CA $137
CA $461 total
includes taxes & fees
Dec 1 - Dec 2
Coastal Breeze Perfect Family Getaway/ Sleep 9

17. Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
4.5 star property
Panama City Beach
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful view. convenient location"
United States
Tien
The price is CA $201
CA $801 total
includes taxes & fees
Nov 8 - Nov 9
Calypso Beach Resort Tower 1

18. Sea Glass Villa! Gulf front! Pool! Dog friendly! Near Pier Park! Beach loungers!

Sea Glass Villa! Gulf front! Pool! Dog friendly! Near Pier Park! Beach loungers!
Panama City Beach
9.8 out of 10, Exceptional, (167 reviews)
"We loved our stay and Jeff and Jill are great to work with!"
United States
Cody D.
The price is CA $118
CA $313 total
includes taxes & fees
Nov 8 - Nov 9
Sea Glass Villa! Gulf front! Pool! Dog friendly! Near Pier Park! Beach loungers!

19. Ocean view from the 13th Floor. Owner Operated.

Ocean view from the 13th Floor. Owner Operated.
Panama City Beach
9.8 out of 10, Exceptional, (278 reviews)
"Had an incredible time. It was the perfect place to stay with my family."
United States
Kelli
The price is CA $119
CA $399 total
includes taxes & fees
Nov 9 - Nov 10
Ocean view from the 13th Floor. Owner Operated.

20. Lovely 1 bedroom beach front studio, amazing beach access and location in PCB

Lovely 1 bedroom beach front studio, amazing beach access and location in PCB
Panama City Beach
9.8 out of 10, Exceptional, (24 reviews)
"A great stay for couples"
United States
Kyla M.
The price is CA $99
CA $320 total
includes taxes & fees
Nov 9 - Nov 10
Lovely 1 bedroom beach front studio, amazing beach access and location in PCB
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?

Beach House - Sunset Paradise by PHG: You might want to consider this Chipley vacation home rental for your stay. It is located by the ocean and offers a private balcony, air-conditioning, and Netflix to help you feel perfectly comfortable in your new surroundings. Amenities like a coffee maker and free parking are also available for your convenience.

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 Pal's Park are a couple of lovely local spots to get outside and enjoy nature. Lucas Lake 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.