Charter Oaks Packages (Flight + Hotel)
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ฿27,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Where to stay in Charter Oaks
Find the best Charter Oaks areas and neighborhoods for the activities you enjoy most. Learn more about Charter Oaks
Pass-a-Grille
1 out of top 10 points of interest in this area
As you view this neighborhood’s iconic pink hotel it feels as if you’ve crossed into the past. Find beautiful beaches and serene enjoyment here.
Downtown St. Petersburg
1 out of top 10 points of interest in this area
Come here for the beaches and sunshine and discover much more in this Florida city with something for all ages and tastes.
Sand Key
1 out of top 10 points of interest in this area
If you're spending some time in Sand Key, Belleair Beach and Sand Key Park are top sights worth seeing.
Sunset Beach
Sunset Beach is noteworthy for its beaches, and you can make a stop at top attractions like Sunset Beach and St. Petersburg Municipal Beach at Treasure Island.
Don Cesar
Don Cesar might not have many top sights, but Splash Island Water Park and Pass-a-Grille Beach are two attractions nearby that you can check out.
Top hotels in Charter Oaks
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
฿6,315
฿8,429 total
27 Aug - 28 Aug
includes taxes & fees
The Westin Tampa Bay
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
฿4,704
฿5,339 total
3 Sept - 4 Sept
includes taxes & fees
Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
฿5,331
฿7,316 total
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very good! (2,955 reviews)
"Staff were amazing and service was excellent. Building itself showing some wear and tear and the pool was very dirty. Loved the ocean access, cabana rentals and the beach booze wagon!"
Reviewed on 22 Aug 2026
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.
Frequently asked questions
How much does a Charter Oaks holiday package cost?
Custom make your Charter Oaks package from as little as . Choose from any combination of rental cars, flights and hotels to pull together the getaway you've been dreaming of. Remember to add on a few experiences or activities!
How do I get a cheap travel package to Charter Oaks?
By bundling. Hotels, rental cars and flights — combine whatever you need into a Charter Oaks holiday package to save a ton of cash. Score even more discounts when you include extras such as tours or experiences to your booking. But that's not the only good part. You have the freedom to customize your trip your own way. We offer more than 550 airlines and 1,000,000 hotels worldwide, so that everyone has an opportunity to travel and live out those holiday dreams.
Where should I stay in Charter Oaks?
A holiday in Charter Oaks isn't complete without stopping by Eddie C. Moore Softball Complex, Westfield Countryside Mall and Bright House Field. Spend your evenings close to these popular attractions and make sightseeing a breeze.
How far in advance should I book my Charter Oaks holiday?
Your safest bet is to book early. Air carriers generally advertise flight tickets around a year ahead of departure, and this is an excellent opportunity to pick up some of the cheapest prices. Boss just told you to take some holiday time in a few weeks? That's alright! Expedia are never short of fantastic bargains to whisk you away on the getaway of your dreams, at a price you can afford.
What does an Expedia Charter Oaks travel package include?
Flights, hotels and rental cars, or any combination of the three — the choice is all yours! Whether you're visiting Charter Oaks with the kids or travelling solo, there's a bundle to fit every style and budget. Once you've made your booking, why not add on a few tours or activities?
What should I know before booking a Charter Oaks travel package?
When you book your flights, hotels and car rentals together, you'll score incredible discounts. Whether you're organising a mountain getaway in a cabin or prefer to stay in a comfortable hotel in the city, Expedia can help make it happen.
Can I choose my airline with a Charter Oaks Expedia holiday package?
Yes — that's one of the best things about an Expedia package. You can pick and choose your flights, hotels and more. We have access to more than 550 partner airlines worldwide, so you have options galore when organising your Charter Oaks adventure.
If I'm not able to travel, can I cancel my Charter Oaks holiday package?
Don't stress if you're rethinking your Charter Oaks holiday package — it's possible to cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We totally understand your circumstances can suddenly change, so head to our Customer Service Portal if that happens. When you're ready to make changes, we're ready to help.
Things to do
Starlite Infinity Evening Yacht Cruise Clearwater
฿1,214
per adult
90% of travellers recommend
Clearwater Beach: Dolphin & Island Sandbar Cruise
฿927
per adult
94% of travellers recommend
Calypso Breeze Tropical Party Buffet Cruise
฿2,382
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.