Oak Shores Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Oak Shores Holiday

Our pick of the best Oak Shores Hotel Deals

Cavalier Oceanfront Resort

Cavalier Oceanfront Resort

3.5 out of 5
9415 Hearst Drive San Simeon CA
Fully refundableReserve now, pay when you stay
The price is NZ$359 per night from 22 July to 23 July
NZ$359
22 July - 23 July
includes taxes & fees
8.8/10 Excellent! (2,003 reviews)
"Staff is very friendly and helpful. We had a view to the ocean. The room are clean. A Happy Place for Dogs. Just a short walk to the beach."

Reviewed on 3 July 2026

Cavalier Oceanfront Resort
Adelaide Inn

Adelaide Inn

3 out of 5
1215 Ysabel Avenue Paso Robles CA
The price is NZ$190 per night from 6 July to 7 July
NZ$190
6 July - 7 July
includes taxes & fees
9.4/10 Exceptional! (2,094 reviews)
"Room was spacious and clean. Was only there for an overnighter but was an enjoyable stay."

Reviewed on 3 July 2026

Adelaide Inn
Silver Surf Motel

Silver Surf Motel

2 out of 5
9390 Castillo Dr San Simeon CA
Fully refundableReserve now, pay when you stay
The price is NZ$151 per night from 4 Aug to 5 Aug
NZ$151
4 Aug - 5 Aug
includes taxes & fees
8.4/10 Very good! (1,457 reviews)
"Just what I needed, a good night sleep."

Reviewed on 4 July 2026

Silver Surf Motel
See all 628 properties in Oak Shores
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 Oak Shores holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday to Oak Shores costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Oak Shores?
Travel in the low season and you're likely to get cheap Oak Shores holiday packages. Keep in mind that public holidays and local events and festivals can impact prices, so do some research before booking.
How many days is enough for Oak Shores?
Usually, a handful of days is enough to go to the main attractions during your Oak Shores holiday. But if you want to have time to relax or take day tours, consider extending your trip.
How to find the best Oak Shores package deals?
Begin your search for an Oak Shores package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Oak Shores package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Oak Shores adventure off to a flying start.
Is it cheaper to book an Oak Shores holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking flights and hotels individually. Better still, you can customise your Oak Shores trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a holiday package to Oak Shores?
Land incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Oak Shores adventure.
How to plan a trip to Oak Shores?

  1. Choose when to travel: Check your diary and get your bags packed. Your preferred season and the activities on offer will also help you decide when to holiday in Oak Shores.
  2. Calculate your budget: Ensure you have enough money to pay for everything from meals and transportation to activities and airfares. Your accommodation will probably be the biggest expense during your trip to Oak Shores.
  3. Work out your trip length: Think about how long you want to spend exploring Oak Shores. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick an Oak Shores holiday package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.