Oakland Hills Holidays

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Our guide on where to stay in Oakland Hills

Find the best Oakland Hills areas and neighborhoods for the activities you enjoy most. Learn more about Oakland Hills
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Pinehurst

When in Pinehurst, you can plan a visit to Don Pedro Island Beach and Stump Pass Beach State Park, some noteworthy sights in the nearby area.

Find hotel + flight trips in Pinehurst

Our pick of the best Oakland Hills Hotel Deals

Sunseeker Resort Charlotte Harbor
Sunseeker Resort Charlotte Harbor
4.5 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
The price is AU$394 per night from 4 Jan to 5 Jan
AU$394
includes taxes & fees
4 Jan - 5 Jan
9.2/10 Wonderful! (677 reviews)
"Sunseeker is a phenomenal destination. The facilities are 5 star and the dining choices are incredible. Not a ton to do off-property in the area, but enough to fill in when you don't want to do the pool all day every day. My family loved it!"

Reviewed on 30 Dec. 2024

Sunseeker Resort Charlotte Harbor
Days Inn by Wyndham Port Charlotte/Punta Gorda
Days Inn by Wyndham Port Charlotte/Punta Gorda
3 out of 5
1941 Tamiami Trl, Port Charlotte, FL
Fully refundableReserve now, pay when you stay
The price is AU$221 per night from 9 Jan to 10 Jan
AU$221
includes taxes & fees
9 Jan - 10 Jan
7.6/10 Good! (1,001 reviews)
Days Inn, Florida
"Nice clean room with minifridge and microwave. Recently remodeled, first floor, convenient parking. Great location with food and shopping. Nice big TV, plenty of pillows."

Reviewed on 1 Jan. 2025

Days Inn by Wyndham Port Charlotte/Punta Gorda
Country Inn & Suites by Radisson, Port Charlotte, FL
Country Inn & Suites by Radisson, Port Charlotte, FL
2.5 out of 5
24244 Corporate Ct, Port Charlotte, FL
Fully refundable
The price is AU$202 per night from 5 Jan to 6 Jan
AU$202
includes taxes & fees
5 Jan - 6 Jan
7.4/10 Good! (1,002 reviews)
"It served the purpose, and the price was reasonable!"

Reviewed on 1 Jan. 2025

Country Inn & Suites by Radisson, Port Charlotte, FL
See all 5,228 properties in Oakland Hills
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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does an Oakland Hills holiday package cost?
Perhaps much less than you think — from only , as a matter of fact! By bundling flights, hotels and car rentals into your own tailor-made travel package, your getaway to Oakland Hills is just clicks away.
How do I get a cheap travel package to Oakland Hills?
Bundle your bookings with Expedia to save on your next adventure. With over 550 air carriers and 1 000 000 properties across the globe, your Oakland Hills holiday package can be customized exactly to suit your travel style. With all those extra dollars, why not include some interesting tours and experiences? It’s an easy way to unlock even more discounts. Your dream holiday in Oakland Hills is much closer than you thought!
What are the top hotels in Oakland Hills?
Get your holiday off to a great start by reserving a room at Designer Home On Fresh Water Canal20x32 Heated Poolclose To Manasota Key Beach. It’s one of most popular properties in Oakland Hills. Another comfortable option is Water Front Boundary Holiday Home Villa Close To Beaches.
How far in advance should I book my Oakland Hills holiday?
It can be tricky to know exactly when the best time is to book your Oakland Hills holiday. But generally the earlier you book, the lower the prices. In some cases, you can reserve your flights and hotels nearly 12 months before departure. If you’re eager to escape on a last-minute getaway, no need to stress! There are terrific bargains advertised on Expedia all the time.
What does an Expedia Oakland Hills travel package include?
Expedia has everything you need to lock in Oakland Hills escape, but what goes into your package is your call. Pick from a combination of hotels, rental cars and flights. In search of some experiences or tours to fill in your time? Once you’ve made your booking, you can add them too. Whatever your budget, there’s a package to meet your needs.
What should I know before booking an Oakland Hills travel package?
A package can be more affordable than separately booking all you need for your trip. For example, bundle your hotels, flights and rental cars and save a tidy sum. Whatever type of holiday you have in mind, you’re sure to find a package within your budget.
Can I choose my airline with an Oakland Hills Expedia holiday package?
Yes, you’re in charge. Expedia has access to more than 550 airlines throughout the world, so you can customize your Oakland Hills escape according to your budget and style.
If I'm not able to travel, can I cancel my Oakland Hills holiday package?
It’s difficult to predict what tomorrow might bring, so it’s good to know that you can change or cancel your Oakland Hills holiday package. If you booked in the last 24 hours, you may be eligible for a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to learn more.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.