Oak Shores Vacations from $366

Book a Hotel + Flight or Car together to unlock savings

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.
Spyglass Inn

Spyglass Inn

3 out of 5
Price was $509, price is now $366 per person
$366
per person
Nov 11 - Nov 14
found 23 hours ago
Roundtrip non-stop flight included
Portland (PDX) to San Luis Obispo (SBP)
9/10 Wonderful! (1,233 reviews)
The view of the ocean and gardens were beautiful. We were disappointed in the room. Furniture was outdated and bed was so-so. The price of the room was too high. The check in went smoothly and was efficient.

Reviewed on Oct 1, 2025

Beach House Inn & Suites

Beach House Inn & Suites

3 out of 5
Downtown Pismo Beach
Save 100% on your flight
Price was $549, price is now $369 per person
$369
per person
Nov 11 - Nov 14
found 23 hours ago
Roundtrip non-stop flight included
Portland (PDX) to San Luis Obispo (SBP)
9.2/10 Wonderful! (461 reviews)
We have stayed in this room 3 times and have been really pleased each time. This time, however, the 2 tv's worked sporadically. There seems to be a problem with the wifi. The king bed is wonderful. The last time we stayed in this room the owner had put a new bed in the room that was uncomfortably firm. Felt like sleeping on the floor. Since then, they put a new mattress in there that is super comfy. Thank you!!!

Reviewed on Sep 19, 2025

Blufftop Inn & Suites - Wharf/Restaurant District

Blufftop Inn & Suites - Wharf/Restaurant District

2 out of 5
Price was $685, price is now $499 per person
$499
per person
Nov 22 - Nov 26
found 22 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to San Luis Obispo (SBP)
9.2/10 Wonderful! (929 reviews)
The room was super cute and updated. The staff was really nice. The only downside was the super thin walls. It sounded like a grizzly bear in cement shoes was in the room above us. Not only loud clomping feer back and forth but the snoring sounded like he was in the same room with us.

Reviewed on Sep 19, 2025

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
Save 100% on your flight
Price was $2,088, price is now $1,529 per person
$1,529
per person
Nov 11 - Nov 14
found 23 hours ago
Roundtrip non-stop flight included
Portland (PDX) to San Luis Obispo (SBP)
No reviews
Garden Street Inn, A Kirkwood Collection Hotel

Garden Street Inn, A Kirkwood Collection Hotel

4 out of 5
Downtown San Luis Obispo
Price was $528, price is now $400 per person
$400
per person
Nov 11 - Nov 14
found 1 hour ago
Roundtrip non-stop flight included
Portland (PDX) to San Luis Obispo (SBP)
9.2/10 Wonderful! (693 reviews)
We thoroughly enjoyed our stay here. The location was convenient and the house was beautiful. The breakfast was delicious. I highly recommend this property and would stay here again.

Reviewed on Sep 21, 2025

Don't see what you're looking for?
See all available trips from Columbus to Oak Shores
View all trips

Discover the most popular places to visit in Oak Shores

Lake San Antonio

Commune with nature and explore the great outdoors at Lake San Antonio during your travels in Bradley. Amble around the area's beaches or experience its museums.

Lake San Antonio

Camp Roberts

Learn about the local history of Bradley when you take a trip to Camp Roberts. Discover the wineries and lively festivals in this walkable area.

Camp Roberts

Oak Paradise Wakeboarding

Enjoy an outing to Oak Paradise Wakeboarding during your stay in Bradley. While you're in the area, stroll along the seaside.

Oak Paradise Wakeboarding

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
$104 nightly
The price is $119 total per night from Oct 5 to Oct 6
$119 total
Oct 5 - Oct 6
Total with taxes and fees
9.2/10 Wonderful! (2,019 reviews)
"Great front desk staff (and home-made cookies). Modern, clean, comfortable, all at a great rate."

Reviewed on Oct 1, 2025

Adelaide Inn
La Quinta Inn & Suites by Wyndham Paso Robles

La Quinta Inn & Suites by Wyndham Paso Robles

3 out of 5
2615 Buena Vista Drive, Paso Robles, CA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $149 total per night from Oct 28 to Oct 29
$149 total
Oct 28 - Oct 29
Total with taxes and fees
9.4/10 Exceptional! (1,973 reviews)
"Clean room and helpful staff."

Reviewed on Sep 25, 2025

La Quinta Inn & Suites by Wyndham Paso Robles
Cavalier Oceanfront Resort

Cavalier Oceanfront Resort

3.5 out of 5
9415 Hearst Drive, San Simeon, CA
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $171 total per night from Nov 2 to Nov 3
$171 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (1,753 reviews)
"My husband and I here stayed one night on a west coast roadtrip and we loved this place. You can tell its old but they keep it updated and in fantastic condition. We had a downstairs room with a porch facing the ocean. The wood burning fireplace was a nic esurprise as was rhe size of the room. There ..."

Reviewed on Sep 30, 2025

Cavalier Oceanfront Resort
See all 740 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.

Oak Shores Essential Information

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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Oak Shores vacation package cost?
You can grab a vacation package to this top destination from $366 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.