Oakland Hills Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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 hotels in Pinehurst

Top hotels in Oakland Hills

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 S$127 per night from 15 Dec to 16 Dec
S$127
includes taxes & fees
15 Dec - 16 Dec
7.6/10 Good! (1,003 reviews)
"Clean"

Reviewed on 20 Nov,2024

Days Inn by Wyndham Port Charlotte/Punta Gorda
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 S$276 per night from 26 Nov to 27 Nov
S$276
includes taxes & fees
26 Nov - 27 Nov
9.2/10 Wonderful! (622 reviews)
"Not much to say. Wish we could have parked out car ourselves and didn’t have to use valet everytime. Also the parking fee nightly was insane. $25 for self park and $32 for valet which we had to do."

Reviewed on 19 Nov,2024

Sunseeker Resort Charlotte Harbor
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 S$118 per night from 8 Dec to 9 Dec
S$118
includes taxes & fees
8 Dec - 9 Dec
7.6/10 Good! (1,008 reviews)
"Nice staff rooms clenef good breakfast"

Reviewed on 21 Nov,2024

Country Inn & Suites by Radisson, Port Charlotte, FL
See all 5,137 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.

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.
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.