Happy Hill Vacations from $413

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Your Happy Hill Vacation

With a vacation package to Happy Hill, say goodbye to endless planning and hello to hassle-free adventure. Every detail of your getaway has been taken care of before you go, so you can spend more time discovering this lively city. Make your trip to Happy Hill even more fun and exciting by including some sightseeing. Nitt Witt Ridge, Moonstone Beach Park and Fiscalini Ranch Preserve are some of the popular attractions you'll want to explore. Browse Expedia's wide range of travel options and begin planning your perfect vacation to Happy Hill today.

The Latest Happy Hill vacation packages

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

Spyglass Inn

3 out of 5
Price was $481, price is now $413 per person
$413
per person
Dec 9 - Dec 11
found 8 hours ago
Roundtrip flight included
San Diego (SAN) to San Luis Obispo (SBP)
8.8/10 Excellent! (1,900 reviews)

The Inn at Zaca Creek

The Inn at Zaca Creek

3.5 out of 5
Save 100% on your flight
Price was $964, price is now $809 per person
$809
per person
Dec 11 - Dec 15
found 18 hours ago
Roundtrip flight included
San Diego (SAN) to San Luis Obispo (SBP)
9.6/10 Exceptional! (160 reviews)
Had an amazing stay! Would definitely stay again

Reviewed on Oct 2, 2026

Sandcastle Hotel on the Beach

Sandcastle Hotel on the Beach

3.5 out of 5
Downtown Pismo Beach
Price was $504, price is now $428 per person
$428
per person
Dec 9 - Dec 11
found 8 hours ago
Roundtrip flight included
San Diego (SAN) to San Luis Obispo (SBP)
9/10 Wonderful! (1,712 reviews)
It was a great stay. Right on the beach.

Reviewed on Oct 28, 2026

Pacific Point Resort

Pacific Point Resort

3 out of 5
Price was $530, price is now $463 per person
$463
per person
Dec 9 - Dec 11
found 8 hours ago
Roundtrip flight included
San Diego (SAN) to San Luis Obispo (SBP)
9/10 Wonderful! (1,335 reviews)
Home away from home Austin is amazing valet too

Reviewed on Oct 28, 2026

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 $1,598, price is now $1,403 per person
$1,403
per person
Dec 9 - Dec 11
found 8 hours ago
Roundtrip flight included
San Diego (SAN) to San Luis Obispo (SBP)
No reviews

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Happy Hill Hotel Deals

Enjoy Fabulous Views at This Rental on Happy Hill! Pet-Friendly Too!

Enjoy Fabulous Views at This Rental on Happy Hill! Pet-Friendly Too!

Cambria CA
9/10 Wonderful! (219 reviews)
"The view was beautiful and the house was very clean and had everything we needed. The only complaint I have is the amount of stairs. I didn't realize that the house was actually a tri level. Having someone in the group with mobility issues and a baby, made it a little difficult"

Reviewed on Oct 7, 2026

Get rates
Enjoy Fabulous Views at This Rental on Happy Hill! Pet-Friendly Too!
Lovely Cottage just above Moonstone Beach in the Pines and Oak Trees.

Lovely Cottage just above Moonstone Beach in the Pines and Oak Trees.

Cambria CA
9.4/10 Exceptional! (138 reviews)
""Beautiful place, clean and very comfortable! The location was perfect, with a fantastic beach just a short distance away. We recommend this rental and would definitely stay here again.""

Reviewed on Oct 26, 2026

Get rates
Lovely Cottage just above Moonstone Beach in the Pines and Oak Trees.
Cavalier Oceanfront Resort

Cavalier Oceanfront Resort

3.5 out of 5
9415 Hearst Drive San Simeon CA
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $152 total per night from Nov 15 to Nov 16
$152 total
Nov 15 - Nov 16
Total with taxes and fees
9/10 Wonderful! (2,191 reviews)
"A decent experience with a beach experience. Wish they had provided water to drink."

Reviewed on Oct 29, 2026

Cavalier Oceanfront Resort
See all 614 properties in Happy Hill
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 Happy Hill Vacation Packages

Happy Hill Essential Information

Language
English
Currency
U.S dollars
Top Sights
Moonstone Beach Park, Fiscalini Ranch Preserve and Santa Rosa Creek Nature Preserve

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Frequently asked questions

How much does a Happy Hill vacation package cost?
You can pick up a vacation package to this destination from $413 on Expedia. However, how much your vacation to Happy Hill costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Happy Hill?
You can usually find reduced prices and greater availability in October, November and December. Take a look at our cheap Happy Hill vacation packages and you could land some excellent off-season deals.
How many days is enough for Happy Hill?
The ideal duration of your Happy Hill vacation depends on what you'd like to do. Generally, a handful of days to a week will give you time to hit all the main sights and explore some hidden treasures along the way.
How to find the best Happy Hill package deals?
Finding a cheap Happy Hill package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, add a few filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Happy Hill package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Happy Hill vacation as a package?
You can enjoy significant savings on your Happy Hill escape by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to view some great airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Happy Hill?
If you're planning a spontaneous Happy Hill vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Happy Hill vacation packages?
Secure your dream trip to Happy Hill with our Book Now, Pay Later vacations. There's no need to scrimp and save or hold off until your next paycheck — we've partnered with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stay on budget and snap up travel deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.