San Luis Obispo Wine Country Vacations from ￥252,062

Book a Hotel + Flight or Car together to unlock savings

Photo by Anthony Hilario

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 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

The Latest San Luis Obispo Wine Country Vacation Packages

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

Sierra Inn

2.5 out of 5
Price was ￥328,622, price is now ￥252,062 per person
￥252,062
per person
Dec 29 - Jan 4
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Los Angeles (LAX)
7.6/10 Good! (33 reviews)
Ok

Reviewed on Sep 8, 2026

SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
South of Wilshire
Save 100% on your flight
Price was ￥520,212, price is now ￥298,484 per person
￥298,484
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Los Angeles (LAX)
8.2/10 Very Good! (1,005 reviews)

The Pierside Santa Monica

The Pierside Santa Monica

4 out of 5
Downtown Santa Monica
Price was ￥462,300, price is now ￥324,056 per person
￥324,056
per person
Dec 27 - Jan 1
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Los Angeles (LAX)
9/10 Wonderful! (1,484 reviews)
Great location, great staff and great restaurant

Reviewed on Oct 26, 2026

The Dixie Hollywood

The Dixie Hollywood

3 out of 5
Hollywood
Price was ￥388,044, price is now ￥283,846 per person
￥283,846
per person
Dec 29 - Jan 4
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Los Angeles (LAX)
7.6/10 Good! (1,005 reviews)

The Huntley Hotel

The Huntley Hotel

4.5 out of 5
Wilshire Montana
Price was ￥514,582, price is now ￥379,647 per person
￥379,647
per person
Dec 27 - Jan 1
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Los Angeles (LAX)
9.4/10 Exceptional! (2,740 reviews)
Perfect classy retreat

Reviewed on Oct 27, 2026

Where to stay in San Luis Obispo Wine Country

Find the best San Luis Obispo Wine Country areas and neighborhoods for the activities you enjoy most. Learn more about San Luis Obispo Wine Country
A coastal landscape with rocky outcrops in the water, a distant mountain range, and a clear sky.

Shell Beach

Visitors to Shell Beach enjoy its beaches, and if you want to do some exploring, Eldwayen Ocean Park is worth a stop.

Find hotels in Shell Beach

Find the Best San Luis Obispo Wine Country Vacation Packages

San Luis Obispo Wine Country Hotel Deals

Apple Farm

Apple Farm

3.5 out of 5
2015 Monterey St San Luis Obispo CA
Fully refundableReserve now, pay when you stay
The price is ￥16,801 per night from Nov 1 to Nov 2
￥16,801
￥20,887 total
Nov 1 - Nov 2
includes taxes & fees
9/10 Wonderful! (1,671 reviews)
"Very friendly accommodating staff. Hotel has undergone some recent renovations, some items such as bathroom sinks and fixtures still need updating. Sinks are old and too shallow, splashing water on counters and floors. Caulking with mold exists from years of attempting to revitalize sinks and the ..."

Reviewed on Oct 27, 2026

Apple Farm
Madonna Inn

Madonna Inn

3.5 out of 5
100 Madonna Road San Luis Obispo CA
The price is ￥21,823 per night from Oct 29 to Oct 30
￥21,823
￥30,132 total
Oct 29 - Oct 30
includes taxes & fees
Madonna Inn
Spyglass Inn

Spyglass Inn

3 out of 5
2705 Spyglass Dr Pismo Beach CA
Fully refundableReserve now, pay when you stay
The price is ￥20,221 per night from Nov 16 to Nov 17
￥20,221
￥23,193 total
Nov 16 - Nov 17
includes taxes & fees
Spyglass Inn
See all 1,938 properties in San Luis Obispo Wine Country
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.

Stay near popular San Luis Obispo Wine Country attractions

A modern architectural building with curved surfaces and palm trees in the foreground.

California Polytechnic State University, San Luis Obispo

9.4/10 (2,266 reviews)
Explore the campus of California Polytechnic State University, San Luis Obispo during your visit to San Luis Obispo. Stroll along the area's seaside, or simply savor its top-notch restaurants.
See properties

Frequently asked questions

How much does a San Luis Obispo Wine Country vacation package cost?
Create unforgettable memories with our San Luis Obispo Wine Country vacation packages, which start from a low ￥252,062. Choose the flights and hotels that match your travel plans. Then, add on some sightseeing activities to cap off your unique adventure.
How do I get a cheap travel package to San Luis Obispo Wine Country?
If you love bargains, bundle your bookings into a San Luis Obispo Wine Country vacation package. Whether you need hotels, flights, rental cars or day tours, you can book everything in one place. You'll have lots of choice at your fingertips too. Expedia has over 550 airlines and 1,000,000 hotels all over the world to take your pick of. Fly with who you want, stay in a place you like and save some cash — now that's the ideal getaway!
What are the top hotels in San Luis Obispo Wine Country?
If you're headed to Avila Beach, you won't do better than Pismo View Inn and Oxford Suites Pismo Beach. Both are comfortable bases for exploring this exciting San Luis Obispo Wine Country city.
How far in advance should I book my San Luis Obispo Wine Country vacation?
Search Expedia to compare international airfares as early as possible. You can generally purchase a seat up to a year before departure. If you can't see your preferred carrier, or you've left things to the last moment, don't worry. Cheap fares to San Luis Obispo Wine Country sometimes occur within weeks of departure.
What does an Expedia San Luis Obispo Wine Country travel package include?
Expedia has all you need to plan your San Luis Obispo Wine Country escape, but how you structure your package is up to you. Choose from a combination of flights, rental cars and hotels. Looking for some experiences or tours to fill in your time? Once you've made your booking, you can add them on too. Whatever your budget or style, there's a deal to suit your needs.
What should I know before booking a San Luis Obispo Wine Country travel package?
Bundling your bookings into a San Luis Obispo Wine Country vacation package is the easiest way to organize your trip. Not only that, you'll save big just for combining your hotels, flights and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a San Luis Obispo Wine Country Expedia vacation package?
Expedia offers access to more than 550 airline partners globally, so you definitely can. Just pick your preferred air carrier and put together your ideal San Luis Obispo Wine Country getaway.
If I'm not able to travel, can I cancel my San Luis Obispo Wine Country vacation package?
Don't stress if you're rethinking your San Luis Obispo Wine Country vacation package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We realize life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.

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.