Oak Shores Vacations from $552

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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.
Blufftop Inn & Suites - Wharf/Restaurant District

Blufftop Inn & Suites - Wharf/Restaurant District

2 out of 5
Downtown Morro Bay
Save 100% on your flight
Price was $908, price is now $552 per person
$552
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Luis Obispo (SBP)
18.4/10 Exceptional! (966 reviews)
The room was nice, the cleaning staff on point! The only critique would be office hours are limited, and though only a block, the hill from the hotel to the warf is extremely steep to walk. Great stay, great room.

Reviewed on Nov 8, 2025

Garden Street Inn, A Kirkwood Collection Hotel

Garden Street Inn, A Kirkwood Collection Hotel

4 out of 5
Downtown San Luis Obispo
Save 100% on your flight
Price was $1,360, price is now $967 per person
$967
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Luis Obispo (SBP)
18.4/10 Exceptional! (712 reviews)
Everything was perfect! Very quaint building and comfortable room. Enjoyed the breakfasts and the staff was super friendly. Loved the personal touch here that you normally don't get in big hotels. Location is perfect for exploring downtown San Luis Obispo by foot. Very enjoyable experience all around!

Reviewed on Nov 16, 2025

Wine Country Estate w/ Pool, Hot Tub The Residence at Truss Wines by Avantstay

Wine Country Estate w/ Pool, Hot Tub The Residence at Truss Wines by Avantstay

3 out of 5
Save 100% on your flight
Price was $8,931, price is now $6,489 per person
$6,489
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to San Luis Obispo (SBP)
No reviews
Bellasera Hotel & Suites Paso Robles, Tapestry by Hilton

Bellasera Hotel & Suites Paso Robles, Tapestry by Hilton

4 out of 5
Save 100% on your flight
Price was $1,006, price is now $762 per person
$762
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Luis Obispo (SBP)
17.6/10 Exceptional! (1,000 reviews)
The staff were great. Very helpful

Reviewed on Nov 7, 2025

Vinyl Vineyards

Vinyl Vineyards

2 out of 5
Save 100% on your flight
Price was $1,192, price is now $903 per person
$903
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Luis Obispo (SBP)
20/10 Exceptional! (1 review)
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Discover the most popular places to visit in Oak Shores

Camp Roberts

4/5(9 reviews)

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

Lake San Antonio

4/5(8 reviews)

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 Historical Museum

You can browse the exhibits at Camp Roberts Historical Museum, a museum with a story of its own, during your travels to Bradley. Discover the lively bars and lively festivals in this walkable area.

Camp Roberts Historical Museum

Oak Shores Hotel Deals

Cavalier Oceanfront Resort

Cavalier Oceanfront Resort

3.5 out of 5
9415 Hearst Drive San Simeon CA
$125 nightly
The price is $141 total per night from Nov 30 to Dec 1
$141 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (1,751 reviews)
Terrific views right on the ocean bluff. Friendly staff, spacious rooms that were clean and full of amenities such as mini bar, fridge, sunken tub and fireplace. Romantic atmosphere. Great restaurant and welcoming grounds with fire pits and games. Very pet friendly.

Reviewed on Nov 12, 2025

Cavalier Oceanfront Resort
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 Dec 1 to Dec 2
$96 total
Dec 1 - Dec 2
Total with taxes and fees
9.2/10 Wonderful! (2,008 reviews)
👍

Reviewed on Nov 15, 2025

Adelaide Inn
Fireside Inn on Moonstone Beach

Fireside Inn on Moonstone Beach

3 out of 5
6700 Moonstone Beach Drive Cambria CA
$137 nightly
The price is $155 total per night from Dec 2 to Dec 3
$155 total
Dec 2 - Dec 3
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
My wife and i had a wonderful stay at this hotel. Quick access to beach and great trails also. Definitely coming back here again!

Reviewed on Nov 10, 2025

Fireside Inn on Moonstone Beach
See all 633 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 $552 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.