Happy Hill Vacation Packages

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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.

Top Happy Hill Vacation Deals

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

FogCatcher Inn

3 out of 5
Price was CA $2,830, price is now CA $2,515 per person
CA $2,515
per person
Jun 4 - Jun 8
found 3 hours ago
Roundtrip flight included
Winnipeg (YWG) to San Luis Obispo (SBP)
8.8/10 Excellent! (1,020 reviews)
Great location, quiet, would recommend!

Reviewed on Apr 25, 2026

Cavalier Oceanfront Resort

Cavalier Oceanfront Resort

3.5 out of 5
Price was CA $2,725, price is now CA $2,565 per person
CA $2,565
per person
Jun 4 - Jun 8
found 3 hours ago
Roundtrip flight included
Winnipeg (YWG) to San Luis Obispo (SBP)
8.8/10 Excellent! (1,898 reviews)
Very nice staff. Works to make your stay nice. Beautiful view.

Reviewed on Apr 26, 2026

Fireside Inn on Moonstone Beach

Fireside Inn on Moonstone Beach

3 out of 5
Price was CA $2,736, price is now CA $2,583 per person
CA $2,583
per person
Jun 4 - Jun 8
found 3 hours ago
Roundtrip flight included
Winnipeg (YWG) to San Luis Obispo (SBP)
8.8/10 Excellent! (1,019 reviews)
Beautiful hotel! We really enjoyed the pool and the fireplace. One downside was no coffee at breakfast. Overall amazing!

Reviewed on Apr 25, 2026

Pelican Inn & Suites

Pelican Inn & Suites

3 out of 5
Price was CA $2,665, price is now CA $2,535 per person
CA $2,535
per person
Jun 4 - Jun 8
found 3 hours ago
Roundtrip flight included
Winnipeg (YWG) to San Luis Obispo (SBP)
8.6/10 Excellent! (1,012 reviews)
The location of this property is fantastic. Right in the center of Moonstone Beach Drive. We booked an ocean view room which had plenty of room and the view was incredible. The hotel itself was just average. A little dated, in need of some work in the bathrooms. There was never staff at the front desk and we were never able to get housekeeping services mid-stay as was promised by the hotel.

Reviewed on Apr 21, 2026

The Rigdon House

The Rigdon House

3 out of 5
Price was CA $2,671, price is now CA $2,571 per person
CA $2,571
per person
Jun 4 - Jun 8
found 3 hours ago
Roundtrip flight included
Winnipeg (YWG) to San Luis Obispo (SBP)
9.6/10 Exceptional! (1,000 reviews)
Wonderful place .. truly a great getaway

Reviewed on Apr 18, 2026

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Happy Hill Hotel Deals

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! (110 reviews)
Quiet place with wild animals roaming around. Great place for vacation

Reviewed on Apr 10, 2026

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

Cambria Pines Lodge

3 out of 5
2905 Burton Dr Cambria CA
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from May 4 to May 5
CA $217
CA $244 total
May 4 - May 5
includes taxes & fees
9.2/10 Wonderful! (1,025 reviews)
Cambria Pines Lodge is a beautiful place. The property is huge and is located near the town and oceanfront. There’s plenty to do if you are looking for activity but it’s also a great place to just relax and enjoy nature. I love that the place is dog friendly but if you taking your pet, be mindful ...

Reviewed on Apr 26, 2026

Cambria Pines Lodge
Cavalier Oceanfront Resort

Cavalier Oceanfront Resort

3.5 out of 5
9415 Hearst Drive San Simeon CA
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from May 10 to May 11
CA $199
CA $224 total
May 10 - May 11
includes taxes & fees
8.8/10 Excellent! (1,901 reviews)
Staff were awesome! Have stayed there many of times.

Reviewed on Apr 26, 2026

Cavalier Oceanfront Resort
See all 595 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.
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Discover the most popular places to visit in Happy Hill

Moonstone Beach Park

Moonstone Beach Park

Spend a leisurely day on this rugged and wild stretch of beach, where the sand glitters with shiny round moonstones and the boardwalk promises staggering views.

Moonstone Beach Park
Fiscalini Ranch Preserve

Fiscalini Ranch Preserve

Follow the walking trails along rugged cliffs, over rolling prairies and under tall pine trees to explore this protected coastline.

Fiscalini Ranch Preserve

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.