Photo by Anthony Creamer

Chipley Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Sept - 14 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Holiday Rentals in Chipley

Calypso Beach Resort by Panhandle Getaways
View from room

Calypso Beach Resort by Panhandle Getaways

3.5 star property
8.8 out of 10, Excellent, (163)
"Great place! Luxurious accommodations and beautiful view of ocean."
Calypso Beach Resort by Panhandle Getaways
Tidewater Beach Resort by Panhandle Getaways
View from property

Tidewater Beach Resort by Panhandle Getaways

3.5 star property
7.2 out of 10, Good, (169)
"There was a little construction going on, but it wasn’t bad. Our stay was great. Communication was awesome. They got back to you in a short amount of time. There was a few issues, but nothing major."
Tidewater Beach Resort by Panhandle Getaways
Splash Beach Resort by Panhandle Getaways
3 outdoor pools

Splash Beach Resort by Panhandle Getaways

3.5 star property
7.4 out of 10, Good, (198)
"Nice place to stay"
Splash Beach Resort by Panhandle Getaways
Edgewater Beach and Golf Resort by Southern Vacation Rentals VI
Property amenity

Edgewater Beach and Golf Resort by Southern Vacation Rentals VI

4.0 star property
8.0 out of 10, Very good, (58)
"Good"
Edgewater Beach and Golf Resort by Southern Vacation Rentals VI
Sterling Breeze by Panhandle Getaways
View from room

Sterling Breeze by Panhandle Getaways

3.5 star property
8.4 out of 10, Very good, (29)
"Great place.. near the pier "
Sterling Breeze by Panhandle Getaways
Grand Panama Beach Resort by Panhandle Getaways
Aerial view

Grand Panama Beach Resort by Panhandle Getaways

3.5 star property
8.4 out of 10, Very good, (98)
"Definitely would stay again! Clean, nice, beautiful views! Would definitely recommend to others "
Grand Panama Beach Resort by Panhandle Getaways
Edgewater Beach & Golf Resort by Panhandle Getaways
Fitness facility

Edgewater Beach & Golf Resort by Panhandle Getaways

3.5 star property
7.6 out of 10, Good, (38)
"Balcony overlooking pool was amazing! Spacious, clean and perfect for our group!"
Edgewater Beach & Golf Resort by Panhandle Getaways
Emerald Isle Beach Resort by Panhandle Getaways
View from room

Emerald Isle Beach Resort by Panhandle Getaways

3.5 star property
9.2 out of 10, Wonderful, (42)
"Stayed in 1902 and it was very clean with an awesome view. Very nice condo facility with great parking for that unit. The facility is not new but well maintained for the amount of use it has had. Would definitely go again. "
Emerald Isle Beach Resort by Panhandle Getaways
Book Now!! Balcony is right on the beachside. Great view of the Emerald Water!
On the beach

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

9.8 out of 10, Exceptional, (242)
"Look forward to staying again "
The price is HK$774
HK$2,282 total
includes taxes & fees
1 Sept - 2 Sept
Book Now!! Balcony is right on the beachside. Great view of the Emerald Water!
Emerald Beach Resort by Southern Vacation Rentals
1 bedroom, individually decorated, individually furnished

Emerald Beach Resort by Southern Vacation Rentals

3.5 star property
7.6 out of 10, Good, (804)
"4th visit and was wonderful as always. Really enjoy staying here with my family."
Emerald Beach Resort by Southern Vacation Rentals
Margaritaville Beach Cottage Resort PCB
Exterior

Margaritaville Beach Cottage Resort PCB

4.0 star property
10.0 out of 10, Exceptional, (4)
"Absolutely relaxing and easy walk to beach and pool- accommodations just beautiful!"
Margaritaville Beach Cottage Resort PCB
Southwind Condo Rentals by Panhandle Getaways
Aerial view

Southwind Condo Rentals by Panhandle Getaways

3.5 star property
8.2 out of 10, Very good, (31)
"Wonderful location. Walk right across the street to the beach. Condo was clean will be back!"
Southwind Condo Rentals by Panhandle Getaways
Origin at Seahaven
Beach nearby

Origin at Seahaven

4.0 star property
9.0 out of 10, Wonderful, (69)
"Great place very convenient location "
The price is HK$761
HK$2,392 total
includes taxes & fees
28 Aug - 29 Aug
Origin at Seahaven
Edgewater Beach and Golf Resort by Southern Vacation Rentals
Pool

Edgewater Beach and Golf Resort by Southern Vacation Rentals

4.0 star property
7.4 out of 10, Good, (2199)
"Great place to stay"
Edgewater Beach and Golf Resort by Southern Vacation Rentals
Prime Gulf Highlands Property: 0.4 Mile to Private Beach & 11 Pools!
Outdoor pool, a heated pool

Prime Gulf Highlands Property: 0.4 Mile to Private Beach & 11 Pools!

9.4 out of 10, Exceptional, (15)
"Short trip down for a wedding. Wonderful stay. Very clean and cozy condo. The community at gulf highlands is also very friendly! We loved our stay. "
The price is HK$570
HK$2,205 total
includes taxes & fees
8 Sept - 9 Sept
Prime Gulf Highlands Property: 0.4 Mile to Private Beach & 11 Pools!
5-Bed Beach House with Private Pool
Property grounds

5-Bed Beach House with Private Pool

9.0 out of 10, Wonderful, (2)
"was in great location pool was alittle smaller than expected but all in all was a beautiful place."
5-Bed Beach House with Private Pool
"Tide Life" - Perfect Sized Family Beach House
Terrace/patio

"Tide Life" - Perfect Sized Family Beach House

10.0 out of 10, Exceptional, (22)
"Beautiful place. Couldn’t ask for a more beautiful View. Easy check in and out. "
"Tide Life" - Perfect Sized Family Beach House
Grand Panama Beach Resort by Southern Vacation Rentals
Pool

Grand Panama Beach Resort by Southern Vacation Rentals

3.5 star property
9.4 out of 10, Exceptional, (12)
"Perfect for a family vacation "
Grand Panama Beach Resort by Southern Vacation Rentals
Paradise for Kids and Parents, 2BR 2Bath Penthouse on the west side of the PCB.
Interior

Paradise for Kids and Parents, 2BR 2Bath Penthouse on the west side of the PCB.

9.8 out of 10, Exceptional, (7)
Paradise for Kids and Parents, 2BR 2Bath Penthouse on the west side of the PCB.
#A Gulf Highlands Cozy Condo-BEACH ACCESS
Private kitchen

#A Gulf Highlands Cozy Condo-BEACH ACCESS

8.0 out of 10, Very good, (9)
"It has everything we were looking for to enjoy our son's baseball tournament, restaurant fences, fun.!!!"
#A Gulf Highlands Cozy Condo-BEACH ACCESS
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.
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

Find out more about Chipley

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 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?

Celadon Beach Resort: This holiday home rental outside of Chipley is located on the beach, and has an outdoor pool, a furnished balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave and a coffee maker. Kick off your shoes and enjoy yourself with an outdoor tennis court and 1 hot tub.

How many holiday rentals are there in Chipley?

Choose from 9 Expedia holiday rentals in Chipley for a memorable holiday.

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 Moss Hill Methodist Church 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.