Ashland Vacation Packages 2026 from $158

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The Latest Ashland Vacation Packages

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

Dream catcher

West Oakland

Save 100% on your flight

$158

per person

Dec 3 - Dec 6

found 2 hours ago

Roundtrip flight included

San Diego (SAN) to Oakland (OAK)

5.4/10 (109 reviews)

My room was great. Super cute and clean. No complaints there. The problem I do have is I was not provided with check-in instructions. It smelled of dog piss quite intensely upon walking up to the property. The real kicker for me was how dirty the shared bathroom was. Toilet was gross, dried urine on the floor, the tub fills with water when showering. Sink covered in little hairs, toilet seat was always left wide open, garbage not emptied once.

Reviewed on Sep 17, 2026

Sonesta Essential Vacaville - Napa Valley

Save 100% on your flight

$449

per person

Dec 16 - Dec 23

found 1 day ago

Roundtrip flight included

Los Angeles (QLA) to Oakland (OAK)

8.8/10 Excellent! (1,006 reviews)

Breakfast was amazing didn’t get a chance to use the other amenities.

Reviewed on Oct 1, 2026

RiverPointe Napa Valley Resort

Stonehouse

Save 100% on your flight

$344

per person

Dec 10 - Dec 13

found 2 hours ago

Roundtrip flight included

Los Angeles (LAX) to Oakland (OAK)

8.8/10 Excellent! (1,498 reviews)

Great location, clean, loved having our car close, easy check in, friendly staff.....we will be coming back.

Reviewed on Sep 30, 2026

Calistoga Inn Restaurant and Brewery

Save 100% on your flight

$323

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Oakland (OAK)

8.4/10 Very Good! (812 reviews)

Definitely check in by 9pm for a smooth checkin process.

Reviewed on Sep 29, 2026

Fairmont Sonoma Mission Inn & Spa

Boyes Hot Springs

Save 100% on your flight

$661

per person

Dec 27 - Dec 30

found 1 day ago

Roundtrip flight included

Burbank (BUR) to Oakland (OAK)

8.8/10 Excellent! (1,002 reviews)

Lovely property

Reviewed on Oct 1, 2026

Where to stay in Ashland

Find the best Ashland areas and neighborhoods for the activities you enjoy most. Learn more about Ashland

A serene lake with a gazebo, a tall tree, and a church tower.

Downtown Oakland

2 out of top 10 points of interest in this area

Central business district with a mix of residential, retail, and office spaces, Downtown Oakland offers an Entertainment District, historic theaters, Oakland Museum, and outdoor retail mall. Easily accessible via BART and AC Transit.

Downtown Berkeley

Take time in Downtown Berkeley to visit attractions like Historic Berkeley and UC Theatre Taube Family Music Hall. You might also appreciate the abundant dining options, and you can hop on the metro at Downtown Berkeley Station to see more of the city.

An aerial view of a coastal city with a large bay, a peninsula with sparse vegetation, and a distant urban skyline.

Albany

The seaside views and shopping are a few reasons travelers visit Albany. Want to see more of the surrounding area? Berkeley Marina and UC Theatre Taube Family Music Hall are a few top sights nearby.

A harbor with a large ship, a marina, and a cityscape in the background.

West Oakland

Major West Coast port and trade center, this bustling area boasts the busiest port in Northern California, surrounded by a picturesque landscape of coastal terrace prairie, oak woodland, and north coastal scrub.

A vibrant mural under a bridge with diverse artistic styles and a cityscape.

Piedmont

Forested hills, lakes and leafy parks surround an upscale city, whose impressive villas provide stunning views of the countryside.

Ashland Hotel Deals

Holiday Inn Golden Gateway by IHG

1500 Van Ness Ave San Francisco CA

Fully refundableReserve now, pay when you stay

$152 nightly

$179 total

Oct 25 - Oct 26

Total with taxes and fees

9/10 Wonderful! (6,358 reviews)

"Parking fee is expensive"

Reviewed on Oct 1, 2026

Hotel Riu Plaza Fisherman's Wharf

2500 Mason St San Francisco CA

Fully refundableReserve now, pay when you stay

$167 nightly

$196 total

Oct 30 - Oct 31

Total with taxes and fees

9/10 Wonderful! (7,664 reviews)

"Exceptional breakfast !!! Very clean! Friendly and helpful staff. Would not hesitate to visit and stay here again! 5 stars!!"

Reviewed on Oct 1, 2026

Handlery Union Square Hotel

351 Geary St San Francisco CA

Fully refundableReserve now, pay when you stay

$148 nightly

$174 total

Nov 1 - Nov 2

Total with taxes and fees

See all 4,111 properties in Ashland

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.