Ashland Vacations from $543
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 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 Ashland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
WorldMark Windsor
Save 100% on your flight
Price was $787, price is now $543 per person
$543
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Oakland (OAK)
9/10 Wonderful! (333 reviews)
Very nice and quiet location. It’s close to stores and all of the wineries. Will be back.
Reviewed on Sep 27, 2025
River Terrace Inn - A Noble House Hotel
Downtown Napa
Save 100% on your flight
Price was $808, price is now $574 per person
$574
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Oakland (OAK)
9/10 Wonderful! (1,005 reviews)
Charge for having your own wine on property and $6. For a coke is crazy after what they charge for the stay and food
Reviewed on Oct 8, 2025
Stanly Ranch, Auberge Collection
Save 100% on your flight
Price was $2,311, price is now $1,676 per person
$1,676
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Oakland (OAK)
9.4/10 Exceptional! (152 reviews)
Great stay! We’ll definitely be back.
Reviewed on Sep 23, 2025
RiverPointe Napa Valley Resort
Stonehouse
Price was $1,123, price is now $837 per person
$837
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Miami (MIA) to Oakland (OAK)
8.8/10 Excellent! (1,315 reviews)
Staff was just above average in friendly and helpful and I mean everyone from front desk to maintenance! Cute, fun place to stay.
Reviewed on Oct 11, 2025
Where to stay in Ashland
Find the best Ashland areas and neighborhoods for the activities you enjoy most. Learn more about Ashland
Downtown Oakland
2 out of top 10 points of interest in this area
3.5/5(342 area reviews)
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.
Ashland Hotel Deals
Holiday Inn Golden Gateway by IHG
1500 Van Ness Ave, San Francisco, CA
Fully refundable
$124 nightly
The price is $146 total per night from Nov 9 to Nov 10
$146 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (4,681 reviews)
"The room was cleaned well. Parking was a plus. We enjoyed our stay. The hotel was close to Pier 39. We felt safe too."
Reviewed on Oct 11, 2025
Hilton San Francisco Financial District
750 Kearny St, San Francisco, CA
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $151 total per night from Oct 19 to Oct 20
$151 total
Oct 19 - Oct 20
Total with taxes and fees
8.6/10 Excellent! (1,874 reviews)
"Room was clean but not the best lighting. Bathroom is a little outdated. Prices for the room + parking in the garage were up there which wasn’t surprising but overall I would stay there again because it’s walkable to many cafes/restaurants etc"
Reviewed on Oct 11, 2025
Hotel Riu Plaza Fisherman's Wharf
2500 Mason St, San Francisco, CA
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $170 total per night from Nov 11 to Nov 12
$170 total
Nov 11 - Nov 12
Total with taxes and fees
8.8/10 Excellent! (6,967 reviews)
"Excellent breakfast and great on site parking"
Reviewed on Oct 11, 2025
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.
Discover the most popular places to visit in Ashland
Jack London Square
Shop, dine and stroll to your heart’s content in this waterside square, named after the novelist who spent his childhood here.
University of California, Berkeley
Enjoy the collegiate vibe when you visit University of California, Berkeley, during your trip to Berkeley. Attend a sporting event or discover the beautiful sunsets in this vibrant area.
Oakland-Alameda County Coliseum
Catch an event at Oakland-Alameda County Coliseum during your trip to Oakland. Experience the entertainment choices and acclaimed theater scene in this walkable area.
Things to do
San Francisco Bridge to Bridge Cruise (90-minutes)
$48
per adult
92% of travellers recommend
California Sunset Cruise (2-hours)
$58
per adult
94% of travellers recommend
San Francisco Big Bus Panoramic Sunset Tour
$42
per adult
82% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.