Ashland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave 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.
Kenwood Inn and Spa
CA $2,987
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Oakland (OAK)
9.6/10 Exceptional! (788 reviews)
Very cute boutique hotel that would be great for couples or adult travelers. Quiet, relaxing pool, outdoor fireplace seating areas, courtyard breakfast, and wine hour were great! Only downside is it’s not walkable to anything and the freeway noise can be heard from the property - although not a problem for us at night. We will definitely stay here again if we are Sonoma! Highly recommend!
Reviewed on Aug 18, 2026
SENZA Hotel
CA $2,152
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Oakland (OAK)
9.4/10 Exceptional! (1,007 reviews)
The hotel is cute and cozy. Spacious bed rooms. The pool wasn’t too crowded. It was the perfect size with nice cabanas to relax. The outside areas have a lot of options to hang out. The hot tub has aggressive jets. Only feedback is that it is a short walk away from the pool. The library restaurant delivery was fast.
Reviewed on Aug 24, 2026
Carneros Resort and Spa
CA $3,922
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Oakland (OAK)
9.2/10 Wonderful! (383 reviews)
We had the best time at Carneros. The rooms were beautiful and well taken care of. It was easy to walk around the property and the view from the pool was gorgeous. If you visit, be sure to have dinner at Farm, relax by the pool, and spend time at the Spa. We look forward to going back!
Reviewed on Aug 22, 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
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.
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.
Piedmont
You'll enjoy the lake views and architecture in Piedmont. You might want to make time for a stop at Piedmont Sports Field or Davie Tennis Stadium.
Albany
The seaside views and shopping are a few reasons travelers visit Albany. Want to see more of the surrounding area? Golden Gate Fields and Berkeley Marina are a few top sights nearby.
South Berkeley
While you're in South Berkeley, take in top sights like Telegraph Avenue and jump on the metro at Ashby Station to see more of the city.
Ashland Hotel Deals
Holiday Inn Golden Gateway by IHG
1500 Van Ness Ave San Francisco CA
Fully refundableReserve now, pay when you stay
CA $205
CA $241 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (6,237 reviews)
"Everything"
Reviewed on Aug 24, 2026
Hotel Riu Plaza Fisherman's Wharf
2500 Mason St San Francisco CA
Fully refundableReserve now, pay when you stay
CA $181
CA $270 total
Aug 31 - Sep 1
includes taxes & fees
Handlery Union Square Hotel
351 Geary St San Francisco CA
Fully refundableReserve now, pay when you stay
CA $220
CA $259 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (3,480 reviews)
"Clean room and facilities! Quiet. Checking in a breeze. Staff wonderful! Close to Union Square, Chinatown, Trolly, shopping. Many restaurants near by."
Reviewed on Aug 24, 2026
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.
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 $1,442. 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
Two Flight Indoor Skydiving Experience
CA $176
per traveller
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.