A panoramic view of a valley with a lake, surrounded by rolling hills and dense forests.

Ashland Vacations from $625

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The Latest Ashland Vacation Packages

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

Jan 13 - Jan 17
Holiday Inn & Suites Oakland Airport by IHG + Flight
Airport District
4 nights
3.0 star property
8.8/10 - Excellent (1,000 reviews)
Roundtrip • Dallas (DFW) - Oakland (OAK)
DAL - OAK • Nonstop OAK - DFW • 1 stop
~~$848~~
$625
per traveler
found 7 hours ago
Holiday Inn & Suites Oakland Airport by IHG
Jan 13 - Jan 17
Archer Hotel Napa + Flight
Downtown Napa
4 nights
4.5 star property
9.6/10 - Exceptional (1,414 reviews)
"The property was very centrally located for girls 2 night wine trip. The room was very clean and appreciated the extra pillows that we had requested. :). My friend also tried the extra pillows. She said she never slept so great and she’s gonna do that at home- (I do it due to medical reasons). The staff was wonderful, just very personable, and very accommodating (I always bring Sees candy and facial masks/cleansers for the front desk staff … some can’t have candy). I’ve been in the travel..."
Reviewed November 6, 2026
Roundtrip • Dallas (DFW) - Oakland (OAK)
DAL - OAK • Nonstop OAK - DFW • 1 stop
~~$1,174~~
$840
per traveler
found 1 day ago
Archer Hotel Napa
Jan 17 - Jan 20
Alila Napa Valley, a Hyatt Luxury Resort + Flight
Downtown St. Helena
3 nights
5.0 star property
9.2/10 - Wonderful (118 reviews)
"Amaizing"
Reviewed October 17, 2026
Roundtrip • Phoenix (PHX) - Oakland (OAK)
PHX - SFO • Nonstop SFO - PHX • 1 stop
Save 100% on your flight
~~$2,005~~
$1,436
per traveler
found 1 day ago
Alila Napa Valley, a Hyatt Luxury Resort
Jan 17 - Jan 20
Solage, Auberge Collection + Flight
Calistoga
3 nights
5.0 star property
9.6/10 - Exceptional (773 reviews)
Roundtrip • Phoenix (PHX) - Oakland (OAK)
PHX - SFO • Nonstop SFO - PHX • 1 stop
Save 100% on your flight
~~$1,417~~
$1,046
per traveler
found 1 day ago
Solage, Auberge Collection
Jan 15 - Jan 18
Casa Osito by Avantstay Pool, Hot Tub & Outdoor Dining Minutes From Sonoma Plaza + Flight
Sonoma
3 nights
3.0 star property
Roundtrip • Los Angeles (LAX) - Oakland (OAK)
LAX - OAK • Nonstop OAK - LAX • 1 stop
Save 100% on your flight
~~$2,144~~
$1,590
per traveler
found 16 hours ago
Casa Osito by Avantstay Pool, Hot Tub & Outdoor Dining Minutes From Sonoma Plaza

Where to stay in Ashland

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

A street scene with a prominent building featuring a large marquee sign reading "OAKLAND."

Downtown Oakland

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.

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The Art Museum Pacific Film Archive building with a modern design, located at the corner of a street with a traffic light and pedestrians nearby.

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.

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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.

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A cityscape with a prominent building featuring a spire and golden lights, set against a backdrop of a sunset sky and distant mountains.

Piedmont

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

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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.

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