Oak Shores Vacations from $664

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Your Oak Shores Vacation

Excellent adventures await when you book a Oak Shores vacation package. Whether you're a foodie, art enthusiast or just a traveler who loves to experience new places, there's something for everyone in this vibrant city. Want to see the sights but don't know where to begin? Any trip to Oak Shores should include Oak Paradise Wakeboarding. Stop dreaming and start traveling. Check out the many options on Expedia today and finally put your Oak Shores vacation plans into motion!

The Latest Oak Shores vacation packages

Price found within the past 48 hours. Click for updated prices.
Paso Robles Inn

Paso Robles Inn

4 out of 5
Downtown Paso Robles
Price was $800, price is now $664 per person
$664
per person
Jan 8 - Jan 10
found 15 hours ago
Roundtrip flight included
Denver (DEN) to San Luis Obispo (SBP)
9.2/10 Wonderful! (1,004 reviews)
Very spacious and upgraded room, all amenities in the room are very nice. The property ground is beautiful and well kept. All staff we interacted with were very courteous and helpful.

Reviewed on Nov 8, 2026

San Luis Creek Lodge

San Luis Creek Lodge

3 out of 5
Price was $1,368, price is now $1,078 per person
$1,078
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Carlsbad (CLD) to San Luis Obispo (SBP)
9.4/10 Exceptional! (1,003 reviews)

Cayucos Sunset Inn B&B

Cayucos Sunset Inn B&B

3.5 out of 5
Price was $1,264, price is now $1,014 per person
$1,014
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Carlsbad (CLD) to San Luis Obispo (SBP)
9.8/10 Exceptional! (262 reviews)

La Lomita Ranch

La Lomita Ranch

3.5 out of 5
Price was $1,424, price is now $1,162 per person
$1,162
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Carlsbad (CLD) to San Luis Obispo (SBP)
9.8/10 Exceptional! (58 reviews)

Sunset Serenity by Avantstay Rooftop w/ Hot Tub & Fire Pit, 3 Blocks to Beach!

Sunset Serenity by Avantstay Rooftop w/ Hot Tub & Fire Pit, 3 Blocks to Beach!

3 out of 5
Price was $1,696, price is now $1,416 per person
$1,416
per person
Dec 9 - Dec 11
found 1 day ago
Roundtrip flight included
San Diego (SAN) to San Luis Obispo (SBP)
No reviews

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Oak Shores Hotel Deals

Adelaide Inn

Adelaide Inn

3 out of 5
1215 Ysabel Avenue Paso Robles CA
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $96 total per night from Nov 29 to Nov 30
$96 total
Nov 29 - Nov 30
Total with taxes and fees
9.4/10 Exceptional! (2,226 reviews)
"Really cute office and property. Friendly staff. The bed was comfortable and the room was cozy. I appreciate the space by the sink and closet. Great location as we needed the freeway nearby. Appears events happen nearby. Restaurants and gas close by. An area with things nearby and yet you felt safe. ..."

Reviewed on Nov 7, 2026

Adelaide Inn
Cavalier Oceanfront Resort

Cavalier Oceanfront Resort

3.5 out of 5
9415 Hearst Drive San Simeon CA
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $142 total per night from Nov 16 to Nov 17
$142 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (2,200 reviews)
"Great experienced! My wife and I had the best week staying at the resort. Peaceful, and the food is excellent! 10/10"

Reviewed on Nov 7, 2026

Cavalier Oceanfront Resort
Silver Surf Motel

Silver Surf Motel

2 out of 5
9390 Castillo Dr San Simeon CA
Fully refundableReserve now, pay when you stay
$56 nightly
The price is $63 total per night from Dec 9 to Dec 10
$63 total
Dec 9 - Dec 10
Total with taxes and fees
Silver Surf Motel
See all 692 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.

Find the Best Oak Shores Vacation Packages

Oak Shores Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
60ºF
Max Temp Summer
85ºF

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Frequently asked questions

How much does an Oak Shores vacation package cost?
You can grab a vacation package to this top destination from $664 on Expedia. However, how much your vacation 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?
You can typically find lower rates and better availability in January, October and December. Explore our cheap Oak Shores vacation packages and you could get some great off-season discounts.
How many days is enough for Oak Shores?
Typically, a handful of days is enough to visit the main sights during your Oak Shores vacation. But if you prefer to have time to rest or go on day trips, think about extending your itinerary.
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 vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels individually. Better still, you can customize 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 vacation 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.
Does Expedia offer Book Now, Pay Later Oak Shores vacation packages?
Your Oak Shores trip is meant to be an escape from your busy life, not a reason for money-related stress. So to give you a bit more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.