Ashland Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Ashland

Price found within the past 48 hours. Click for updated prices.
Claremont Resort & Club

Claremont Resort & Club

5 out of 5
Claremont Hills
Price was CA $1,608, price is now CA $1,077 per person
CA $1,077
per person
Jul 3 - Jul 7
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Oakland (OAK)
9/10 Wonderful! (1,005 reviews)
If you are visiting your child at Cal, staying at the Claremont is a no-brainer if you are looking for a bit (or a lot) more than a typical hotel stay.

Reviewed on Apr 13, 2026

Solage, Auberge Collection

Solage, Auberge Collection

5 out of 5
Price was CA $3,792, price is now CA $2,506 per person
CA $2,506
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
9.6/10 Exceptional! (713 reviews)
Lovely…simply lovely!

Reviewed on Mar 29, 2026

Stanly Ranch, Auberge Collection

Stanly Ranch, Auberge Collection

5 out of 5
Price was CA $4,514, price is now CA $3,224 per person
CA $3,224
per person
Jun 4 - Jun 7
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Oakland (OAK)
9.4/10 Exceptional! (205 reviews)
Incredible stay!! Amazing staff!

Reviewed on Mar 29, 2026

the cottages of napa valley

the cottages of napa valley

4 out of 5
Price was CA $1,923, price is now CA $1,409 per person
CA $1,409
per person
Jun 4 - Jun 7
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Oakland (OAK)
10/10 Exceptional! (19 reviews)
Beautiful cottage and amenities. LOVED the morning delivery of baked goods, and the jacuzzi tub. Truly the best romantic getaway in Napa.

Reviewed on Apr 12, 2026

Bardessono Hotel and Spa

Bardessono Hotel and Spa

5 out of 5
Price was CA $2,837, price is now CA $2,078 per person
CA $2,078
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
9.8/10 Exceptional! (681 reviews)
It’s a wonderful place.

Reviewed on Feb 17, 2026

Where to stay in Ashland

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

Downtown Oakland

1 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.

Find hotels in Downtown Oakland

Ashland Hotel Deals

Hotel Riu Plaza Fisherman's Wharf

Hotel Riu Plaza Fisherman's Wharf

4 out of 5
2500 Mason St San Francisco CA
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from May 25 to May 26
CA $167
CA $252 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (7,404 reviews)
Hidden fee is too high

Reviewed on May 1, 2026

Hotel Riu Plaza Fisherman's Wharf
Holiday Inn Golden Gateway by IHG

Holiday Inn Golden Gateway by IHG

3.5 out of 5
1500 Van Ness Ave San Francisco CA
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from May 25 to May 26
CA $172
CA $202 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (5,650 reviews)
I think that a valet service would have been great. With parking at 49/night plus tax and an odd flow of traffic in and out of the front of the hotel it would has been very helpful

Reviewed on May 1, 2026

Holiday Inn Golden Gateway by IHG
Hilton San Francisco Financial District

Hilton San Francisco Financial District

4 out of 5
750 Kearny St San Francisco CA
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from May 25 to May 26
CA $158
CA $186 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (2,707 reviews)
Elevators could be renovated, nothing major

Reviewed on Apr 30, 2026

Hilton San Francisco Financial District
See all 4,349 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Ashland vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Ashland from just CA $1,077. And the more you bundle, the more cash you save. The vacation of your dreams has never been so affordable.
How do I get a cheap travel package to Ashland?
Creating your own Ashland vacation package with Expedia is a simple way to save. We offer more than 550 partner airlines and 1,000,000 hotels spread across the globe. With such an awesome range to select from, you'll have no difficulty pulling together your next dream vacation.
What are the top hotels in Ashland?
Whether you'll be staying for a night or a week in Ashland, you'll get a great night's sleep at Cozy Eclectic 1bedroom Island - Vibe Oasis In Hayward 1 Bedroom Apts. This place is the first choice for many travelers.
How far in advance should I book my Ashland vacation?
It can be tricky to know when is the ideal time to book your Ashland trip. But typically the earlier you book, the better the prices. Sometimes, you can secure your flights and hotels nearly 12 months prior to your departure date. If you're considering a last-minute getaway, no need to panic! There are terrific bargains posted on Expedia every day.
What does an Expedia Ashland travel package include?
Hotels, flights and a reliable car for all your road trip adventures. Simply choose your favorite bundle and get access to incredible deals. Once you've made your booking, add on some sightseeing tours and watch your savings grow. When it comes to organizing your Ashland trip, the choice is all yours!
What should I know before booking an Ashland travel package?
A travel package can be tailored to your budget and is a simple way to make your money go further. How little or much you include is up to you. Hotels, rental cars and flights — mix and match whatever combination suits your style.
Can I choose my airline with an Ashland Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines around the world. Our vacation packages give you the freedom to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Ashland vacation package?
We totally understand that life doesn't always go according to plan. If you've locked in an Ashland vacation package and need to cancel or change it, we can help. We recommend having a look at our Customer Service Portal first for information. But generally, if you've booked your package in the last 24 hours, you may be able to amend or cancel your itinerary for free. If it's been more than 24 hours, your airline, hotel or car rental company may impose a charge.

Discover the most popular places to visit in Ashland

Jack London Square

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.

Jack London Square
University of California, Berkeley

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.

University of California, Berkeley
Oakland Zoo

Oakland Zoo

Watch alligators being fed, ride a train through the Australian outback and see a herd of elephants on the African savannah at this animal park.

Oakland Zoo

Things to do

Bridge 2 Bridge Tour: Golden Gate Bridge to Bay Bridge

San Francisco Bridge to Bridge Cruise (90-minutes)

CA $66
per adult
94% of travellers recommend
San Francisco Bridge to Bridge Cruise (90-minutes)
Golden Gate Bridge at night

San Francisco Night Tour

CA $73
per adult
78% of travellers recommend
San Francisco Night Tour
Alcatraz Visit with Night Option and SF Bay Cruise

Alcatraz Visit with Night Option and SF Bay Cruise

CA $192
per adult
94% of travellers recommend
Alcatraz Visit with Night Option and SF Bay Cruise
See all activities in Oakland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.