Charter Oaks Vacations

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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

Pass-a-Grille

5/5(26 area reviews)

Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.

Find hotels in Pass-a-Grille

Charter Oaks Hotel Deals

Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
The price is ￥27,718 per night from Aug 7 to Aug 8
￥27,718
￥37,211 total
Aug 7 - Aug 8
includes taxes & fees
8/10 Very Good! (2,020 reviews)
"Location is excellent , right on the beach and we had early check in which was awesome. So many extra charges when you get to the property . Did not like the valet parking ( makes each outing time consuming ) Room was very far located from the main lobby . But overall very pleasant experience and ..."

Reviewed on Jul 15, 2025

Hilton Clearwater Beach Resort & Spa
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
4860 West Kennedy Boulevard, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is ￥22,033 per night from Aug 17 to Aug 18
￥22,033
￥25,008 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,658 reviews)
"The property is beautiful and has so many amenities"

Reviewed on Jul 16, 2025

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
The price is ￥40,676 per night from Aug 5 to Aug 6
￥40,676
￥51,811 total
Aug 5 - Aug 6
includes taxes & fees
9.2/10 Wonderful! (2,376 reviews)
"Beautiful view"

Reviewed on Jul 16, 2025

Wyndham Grand Clearwater Beach
See all 14,620 properties in Charter Oaks
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 vacation 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 vacation 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 vacation dreams.
Where should I stay in Charter Oaks?
A vacation 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 vacation?
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 vacation 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 traveling 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 organizing 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 vacation 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 organizing your Charter Oaks adventure.
If I'm not able to travel, can I cancel my Charter Oaks vacation package?
Don't stress if you're rethinking your Charter Oaks vacation 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.

Discover the most popular places to visit in Charter Oaks

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4.5/5(1,625 reviews)

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the seaside in this family-friendly area, or check out its lively bars.

John's Pass Village & Boardwalk
Fort De Soto Park which includes a sandy beach

Fort De Soto Park

4.5/5(676 reviews)

Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.

Fort De Soto Park
Tropicana Field

Tropicana Field

4.5/5(591 reviews)

Catch an event at Tropicana Field during your trip to St. Petersburg. Attend a baseball game or simply enjoy the lively bars while you're in the area.

Tropicana Field

Things to do

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

￥4,698
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

￥5,424
per adult
94% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
Sea Screamer boat in Orlando

Day Trip to Clearwater Beach with Sea Screamer Ride

￥18,324
per adult
90% of travellers recommend
Day Trip to Clearwater Beach with Sea Screamer Ride
See all activities in St. Petersburg - Clearwater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.