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Chipley Vacation Rentals

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Vacation Rentals in Chipley

Calypso Beach Resort by Panhandle Getaways

3.5 star property
8.8 out of 10, Excellent, (164)
"Great place! Luxurious accommodations and beautiful view of ocean."
Calypso Beach Resort by Panhandle Getaways

Tidewater Beach Resort by Panhandle Getaways

3.5 star property
7.2 out of 10, Good, (170)
"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."
The price is CA $243
CA $841 total
includes taxes & fees
Aug 30 - Aug 31
Tidewater Beach Resort by Panhandle Getaways

Splash Beach Resort by Panhandle Getaways

3.5 star property
7.4 out of 10, Good, (198)
"Nice place to stay"
The price is CA $254
CA $888 total
includes taxes & fees
Sep 1 - Sep 2
Splash Beach Resort by Panhandle Getaways

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

3.5 star property
8.4 out of 10, Very good, (30)
"Great place.. near the pier "
Sterling Breeze by Panhandle Getaways

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

3.5 star property
7.6 out of 10, Good, (38)
"Balcony overlooking pool was amazing! Spacious, clean and perfect for our group!"
The price is CA $309
CA $1,304 total
includes taxes & fees
Sep 1 - Sep 2
Edgewater Beach & Golf Resort by Panhandle Getaways

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!

9.8 out of 10, Exceptional, (242)
"Look forward to staying again "
The price is CA $138
CA $402 total
includes taxes & fees
Sep 28 - Sep 29
Book Now!! Balcony is right on the beachside. Great view of the Emerald Water!

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

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

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

4.0 star property
9.0 out of 10, Wonderful, (69)
"Great place very convenient location "
The price is CA $134
CA $422 total
includes taxes & fees
Sep 7 - Sep 8
Origin at Seahaven

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!

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 CA $93
CA $380 total
includes taxes & fees
Sep 9 - Sep 10
Prime Gulf Highlands Property: 0.4 Mile to Private Beach & 11 Pools!

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

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

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.

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

8.0 out of 10, Very good, (9)
"It was a great place to stay for a week."
The price is CA $89
CA $287 total
includes taxes & fees
Sep 16 - Sep 17
#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.
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Top Chipley Hotel Reviews

Find out more about Chipley

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chipley vacation rentals we have selected for you start as low as CA $90 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 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?

Celadon Beach Resort: You might want to consider this vacation rental near Chipley, which is located on the beach and has an outdoor pool, a furnished balcony, and a barbecue grill 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 a hot tub.

How many vacation rentals are there in Chipley?

Choose from 9 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. Pal's Park and Moss Hill Methodist Church 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.