Ashland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

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 $3,297, price is now CA $1,574 per person
CA $1,574
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Oakland (OAK)
9/10 Wonderful! (1,049 reviews)

Lavender, A Four Sisters Inn

Lavender, A Four Sisters Inn

4 out of 5
Price was CA $2,504, price is now CA $1,824 per person
CA $1,824
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
8.8/10 Excellent! (447 reviews)
Everything was great, the outside sitting areas were delightful. The breakfast was great and the staff were the best.

Reviewed on Jun 9, 2026

Carneros Resort and Spa

Carneros Resort and Spa

5 out of 5
Price was CA $6,173, price is now CA $4,500 per person
CA $4,500
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Oakland (OAK)
9.2/10 Wonderful! (378 reviews)

Okaeri Calistoga

Okaeri Calistoga

4.5 out of 5
Price was CA $3,801, price is now CA $2,812 per person
CA $2,812
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Oakland (OAK)
10/10 Exceptional! (23 reviews)
This property is incredible. New, clean, fantastic breakfast, wonderful decor, and lovely staff. Just a few minutes from the main street in Calistoga. If you are looking for a small luxury bed and breakfast with excellent service and a wonderful breakfast, this is a must.

Reviewed on Jul 28, 2026

Chic Sonoma Oasis w/ Pool, Bocce, Hot Tub + Minutes to Downtown

Chic Sonoma Oasis w/ Pool, Bocce, Hot Tub + Minutes to Downtown

3 out of 5
Price was CA $8,699, price is now CA $6,443 per person
CA $6,443
per person
Sep 1 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Oakland (OAK)
No reviews

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.

Find hotels in Downtown Oakland

Ashland Hotel Deals

Holiday Inn Golden Gateway by IHG

Holiday Inn Golden Gateway by IHG

3.5 out of 5
1500 Van Ness Ave San Francisco CA
The price is CA $214 per night from Aug 23 to Aug 24
CA $214
CA $251 total
Aug 23 - Aug 24
includes taxes & fees
9/10 Wonderful! (6,089 reviews)
"Room and other furnitures are old and scratches"

Reviewed on Jul 30, 2026

Holiday Inn Golden Gateway by IHG
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 $233 per night from Aug 13 to Aug 14
CA $233
CA $332 total
Aug 13 - Aug 14
includes taxes & fees
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 $279 per night from Aug 2 to Aug 3
CA $279
CA $393 total
Aug 2 - Aug 3
includes taxes & fees
9.2/10 Wonderful! (2,383 reviews)
"So modern clean and friendly"

Reviewed on Jul 29, 2026

Hyatt Regency San Francisco
See all 4,236 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 $1,574. 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.

Things to do

Alamedas First Walking Food Tour

Alamedas First Walking Food Tour

CA $112
per adult
Alamedas First Walking Food Tour
Two Flight Indoor Skydiving Experience

Two Flight Indoor Skydiving Experience

CA $177
per traveller
80% of travellers recommend
Two Flight Indoor Skydiving Experience
Alameda Walking Tour Experience

Alameda Walking Tour Experience

CA $107
per adult
Alameda Walking Tour 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.