Ashland Vacation Packages

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Top Holiday Package Deals in Ashland

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

Silverado Resort

4 out of 5
Price was CA $1,430, price is now CA $935 per person
CA $935
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
8.8/10 Excellent! (1,029 reviews)
I did not like the stacked parking. My car got blocked in by another guests car when I parked.

Reviewed on Aug. 27, 2025

Vino Bello Resort

Vino Bello Resort

4 out of 5
Soscol Gateway South
Price was CA $1,628, price is now CA $1,025 per person
CA $1,025
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
8.4/10 Very Good! (1,002 reviews)
Beautiful property. Spacious and clean.

Reviewed on Jul. 28, 2025

Solage, Auberge Resorts Collection

Solage, Auberge Resorts Collection

5 out of 5
Price was CA $3,175, price is now CA $2,081 per person
CA $2,081
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
9.6/10 Exceptional! (667 reviews)
Can’t wait to come back.

Reviewed on Aug. 19, 2025

Alila Napa Valley, a Hyatt Luxury Resort

Alila Napa Valley, a Hyatt Luxury Resort

5 out of 5
Price was CA $5,354, price is now CA $3,532 per person
CA $3,532
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
9.4/10 Exceptional! (107 reviews)
Great Vineyard view and staff was very accommodating!

Reviewed on Mar. 20, 2025

Hotel Yountville

Hotel Yountville

4 out of 5
Price was CA $2,663, price is now CA $1,779 per person
CA $1,779
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
9.6/10 Exceptional! (1,007 reviews)
Great hotel, highly recommend

Reviewed on Aug. 28, 2025

Where to stay in Ashland

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

2 out of top 10 points of interest in this area
3/5(9 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.

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 $160 per night from Sep 1 to Sep 2
CA $160
CA $245 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (6,707 reviews)
"water pressure is pretty low."

Reviewed on Aug. 25, 2025

Hotel Riu Plaza Fisherman's Wharf
Hyatt Regency San Francisco

Hyatt Regency San Francisco

4 out of 5
5 Embarcadero Center, San Francisco, CA
Fully refundableReserve now, pay when you stay
The price is CA $234 per night from Aug 31 to Sep 1
CA $234
CA $341 total
Aug 31 - Sep 1
includes taxes & fees
9.2/10 Wonderful! (1,820 reviews)
"beautiful clean great location"

Reviewed on Aug. 24, 2025

Hyatt Regency San Francisco
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 refundable
The price is CA $186 per night from Sep 8 to Sep 9
CA $186
CA $219 total
Sep 8 - Sep 9
includes taxes & fees
8.8/10 Excellent! (4,457 reviews)
"Breakfast buffet iver lriced but iverall a good experience"

Reviewed on Aug. 25, 2025

Holiday Inn Golden Gateway by IHG
See all 4,792 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
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Family Vacations
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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 $935. 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-Alameda County Coliseum

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.

Oakland-Alameda County Coliseum

Things to do

San Francisco: Airplane Bay Tour

San Francisco: Airplane Private Bay Tour

CA $398
per adult
100% of travellers recommend
San Francisco: Airplane Private Bay Tour
Napa Valley: Airplane Napa Valley Tour

Napa Valley: Airplane Napa Valley Tour

CA $439
per adult
Napa Valley: Airplane Napa Valley Tour
Two Flight Indoor Skydiving Experience

Two Flight Indoor Skydiving Experience

CA $164
per traveller
Two Flight Indoor Skydiving Experience
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.