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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chipley holiday rentals

An indoor swimming pool with a long, narrow shape, surrounded by walls with large windows.

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 £113
includes taxes & fees
10 Nov - 11 Nov
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery
A living room with a brown sofa, a white sofa, and a coffee table. There is a door leading outside.

2. The Cozy Farmhouse Retreat

The Cozy Farmhouse Retreat
Chipley
The price is £453
includes taxes & fees
19 Nov - 20 Nov
The Cozy Farmhouse Retreat
An indoor swimming pool with a view of the outside.

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 £176
includes taxes & fees
10 Nov - 11 Nov
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
A wooden boardwalk leading to a lake with trees and a gazebo.

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 £495
includes taxes & fees
10 Nov - 11 Nov
4-bedroom Lake House 45 Minutes from the Beach!
A single-story building with a gabled roof, a front porch with a bench, and a large planter with flowers.

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 £245
includes taxes & fees
10 Nov - 11 Nov
Charming In-town Bungalow
A wooden staircase leading to a house with a deck, surrounded by trees and a lawn.

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 £207
includes taxes & fees
10 Nov - 11 Nov
Charming waterfront barndominium on the beautiful spring-fed Chipola River.
A high-rise hotel with a beach view, multiple balconies, and a pool area.

7. 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 £438
includes taxes & fees
11 Nov - 12 Nov
Calypso Tower 3 by Panhandle Getaways
A covered porch with a table and chairs, a ceiling fan, and a view of the outdoors.

8. 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 £222
includes taxes & fees
10 Nov - 11 Nov
Private - Waterfront Cottage - Panama City, FL
A beach view with a pier extending into the ocean, clear skies, and a balcony overlooking the scene.

9. 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 £459
includes taxes & fees
11 Nov - 12 Nov
Calypso Beach Resort Tower 2 by Panhandle Getaways
A living room with a TV, wooden coffee table, and a sofa. It has a balcony with a view of the ocean.

10. 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 £165
includes taxes & fees
12 Nov - 13 Nov
Origin At Seahaven
A balcony with a view of the ocean and beach, wooden furniture, and a yellow awning.

11. Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
4.5 star property
Panama City Beach
9.0 out of 10, Wonderful, (16 reviews)
"Beautiful view. convenient location"
United States
Tien
The price is £435
includes taxes & fees
11 Nov - 12 Nov
Calypso Beach Resort Tower 1
A balcony with a view of a beach, a palm tree, and a 'No Smoking' sign.

12. Newly renovated studio on the beach # 304

Newly renovated studio on the beach # 304
Panama City Beach
9.4 out of 10, Exceptional, (25 reviews)
"The room was clean and had everything we needed for our stay. The view from the front door of the beach was beautiful! I would stay with them again!"
United States
Whitney F.
The price is £219
includes taxes & fees
10 Nov - 11 Nov
Newly renovated studio on the beach # 304
A modern living room with a sofa, a coffee table, and a dining area with chairs.

13. Octa Collection on Front Beach

Octa Collection on Front Beach
4.5 star property
Long Beach
The price is £248
includes taxes & fees
18 Nov - 19 Nov
Octa Collection on Front Beach
A deck with two chairs, a table with a fruit plate, drinks, and a view of the ocean.

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 £282
includes taxes & fees
1 Dec - 2 Dec
Splash Resort 605E•Best in PCB•Beach Chairs•Crib•Fireplace
A modern living room with a sofa, a coffee table, and a large sliding glass door leading to a balcony with a view of the ocean.

15. 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 £147
includes taxes & fees
28 Nov - 29 Nov
Polynesian #104 Ground Level
A hotel room with a bed, a dining table with chairs, a ceiling fan, and a view of the ocean.

16. 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 £216
includes taxes & fees
15 Nov - 16 Nov
Origin 0538- Studio - Breath Taking Gulf Views
A balcony with a view of the ocean, a glass door, and a seating area with chairs and a table.

17. Tidewater - Breathtaking first-line ocean views! Walking distance to Pier Park

Tidewater - Breathtaking first-line ocean views! Walking distance to Pier Park
Panama City Beach
9.6 out of 10, Exceptional, (28 reviews)
"The room was very clean and well taken care of! Would stay there again!"
United States
Kiley S.
The price is £276
includes taxes & fees
10 Nov - 11 Nov
Tidewater - Breathtaking first-line ocean views! Walking distance to Pier Park
A swimming pool with lounge chairs and palm trees, surrounded by a building with multiple floors and balconies.

18. 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, (279 reviews)
"Had an incredible time. It was the perfect place to stay with my family."
United States
Kelli
The price is £217
includes taxes & fees
10 Nov - 11 Nov
Ocean view from the 13th Floor. Owner Operated.
An indoor swimming pool with clear glass walls, a tiled floor, and a view of palm trees outside.

19. Aqua Beach Resort by Panhandle Getaways

Aqua Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
9.4 out of 10, Exceptional, (15 reviews)
"Great stay"
United States
Justin
The price is £438
includes taxes & fees
10 Nov - 11 Nov
Aqua Beach Resort by Panhandle Getaways
A bedroom with a bed, a dresser, a nightstand, a lamp, a painting, and a window with curtains.

20. 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 £232
includes taxes & fees
2 Dec - 3 Dec
Coastal Breeze Perfect Family Getaway/ Sleep 9
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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Find holiday rentals that suit your style

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Top Chipley Hotel Reviews

A spacious living area with a fireplace, seating, and a high ceiling with fans.
Magnolia Creek Lodge

Magnolia Creek Lodge

Magnolia Creek Lodge
Cottonwood

10/10 Excellent

There is a buffet breakfast and drinks, but no restaurant, but it doesn’t matter, this is a lovely place to stay. The staff are incredibly nice and the rooms lovely. There are plenty of nice restaurants close by, a definite yes to this one.
United Kingdom
Anonymous traveller
Reviewed May 13, 2019
Magnolia Creek Lodge

Find out more about Chipley

Everything you need to know about Chipley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chipley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chipley holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chipley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chipley holiday rentals we have selected for you start as low as £112 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chipley rentals

At Expedia, we put the best Chipley holiday 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 holiday.

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 holiday rentals in Chipley?

Yes, there are holiday rentals close to the most popular sights in Chipley, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Chipley has to offer?

Beach House - Sunset Paradise by PHG: This holiday home rental outside Chipley 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 such as a coffee maker and free parking are also available for your convenience.

How many holiday rentals are there in Chipley?

Choose from 6 Expedia holiday rentals in Chipley for a memorable holiday.

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 holiday rentals like in Chipley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chipley. Holiday rentals feature extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.