Pleasanton Vacation Packages

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Your Pleasanton Vacation

When a fun city getaway is calling, answer it with a vacation package to Pleasanton. The neighborhood of Vineyards - Avalon, which is good for hiking, views and walking, makes a terrific base for your adventures. Fill your itinerary with tours of San Francisco Premium Outlets, Alameda County Fairgrounds and Tommy Ts Comedy House, some of the attractions you just have to see during your trip to Pleasanton. Whoever you're heading away with and whatever you want to spend, your ultimate Pleasanton vacation is just a few clicks away with Expedia.

Top Pleasanton Vacation Deals

Price found within the past 48 hours. Click for updated prices.
RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort

3 out of 5
Stonehouse
per person
Sep 15 - Sep 19
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
8.8/10 Excellent! (1,286 reviews)
Lovely and cute cabins with nice pool and hot tub. Staff was very friendly.

Reviewed on Aug. 3, 2025

Silverado Resort

Silverado Resort

4 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Oakland (OAK)
8.8/10 Excellent! (1,020 reviews)
Great place but the market meds to be better

Reviewed on Aug. 9, 2025

Vino Bello Resort

Vino Bello Resort

4 out of 5
Soscol Gateway South
per person
Sep 15 - Sep 19
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
8.4/10 Very Good! (1,001 reviews)
Beautiful property. Spacious and clean.

Reviewed on Jul. 28, 2025

Claremont Resort & Club

Claremont Resort & Club

5 out of 5
Claremont Hills
per person
Sep 27 - Oct 1
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Oakland (OAK)
8.8/10 Excellent! (1,008 reviews)
Incredible views! Very friendly staff Amazing amenities

Reviewed on Aug. 9, 2025

Hotel Yountville

Hotel Yountville

4 out of 5
per person
Sep 15 - Sep 19
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
9.6/10 Exceptional! (1,000 reviews)
Beautiful room. Great service. The pumps for the conditioner, shampoo and body wash don’t pump easily and the bottles were hard to read. The spa uses the room’s bath. I would rather bathe in a larger pool of hot mineral water. I could have set up my own bath.

Reviewed on Jul. 31, 2025

Ready to book your vacation to Pleasanton?

 

Choose your dates

Pleasanton Hotel Deals

Four Points by Sheraton Pleasanton

Four Points by Sheraton Pleasanton

3 out of 5
5115 Hopyard Rd, Pleasanton, CA
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Aug 14 to Aug 15
CA $144
CA $161 total
Aug 14 - Aug 15
includes taxes & fees
7.6/10 Good! (1,002 reviews)
Rude neighbor
"The only problem we had was the person next door was playing the TV very loud all night."

Reviewed on Aug. 8, 2025

Four Points by Sheraton Pleasanton
Sonesta Silicon Valley

Sonesta Silicon Valley

4 out of 5
1820 Barber Ln, Milpitas, CA
Fully refundable
The price is CA $137 per night from Sep 5 to Sep 6
CA $137
CA $157 total
Sep 5 - Sep 6
includes taxes & fees
9/10 Wonderful! (1,564 reviews)
"All the staff I interacted with were pleasant and professional, with a special shout-out to Premesh, who works in the restaurant."

Reviewed on Aug. 6, 2025

Sonesta Silicon Valley
Shashi Hotel Mountain View Palo Alto

Shashi Hotel Mountain View Palo Alto

5 out of 5
1625 N Shoreline Blvd, Mountain View, CA
The price is CA $183 per night from Aug 31 to Sep 1
CA $183
CA $202 total
Aug 31 - Sep 1
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"Would be 10/10 but not having a way to block out the street lights at night and morning sun really messed up our sleep. That’s the only flaw we found, we loved this hotel!"

Reviewed on Aug. 5, 2025

Shashi Hotel Mountain View Palo Alto
See all 2,514 properties in Pleasanton
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.
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Discover the most popular places to visit in Pleasanton

Stoneridge Shopping Center

During your trip to Pleasanton, you can enjoy retail therapy at Stoneridge Shopping Center. Attend a sporting event in this family-friendly area.

Stoneridge Shopping Center

Tommy T's Comedy House

You can enjoy a show at Tommy T's Comedy House during your stay in Pleasanton. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Tommy T's Comedy House

What to do in Pleasanton

San Francisco: Airplane Bay Tour

San Francisco: Airplane Private Bay Tour

CA $396
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 $437
per adult
Napa Valley: Airplane Napa Valley Tour
Wine tasting at 3 picturesque wineries, and includes a custom deli-style lunch!

4 Hour Livermore Valley Wine Tour

CA $137
per adult
4 Hour Livermore Valley Wine Tour
See all activities in Pleasanton

Frequently asked questions

How much does a Pleasanton vacation package cost?
Offering excellent value package deals from CA $788 on Expedia, you'll be thrilled with how little a vacation to Pleasanton costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Pleasanton?
If you're looking to book a cheap Pleasanton vacation package, consider visiting in January, February and March. You're likely to find lower prices on hotels and airfares during these months — ideal for budget-conscious travellers.
How many days is enough for Pleasanton?
Typically, a handful of days is enough to check out the top attractions during your Pleasanton vacation. However, if you prefer to have time to relax or go on day trips, think about extending your trip.
Is it worth booking a vacation package to Pleasanton?
Pleasanton offers everything you need for a wonderful escape. Begin your Pleasanton vacation on a high note by checking out popular attractions like Alameda County Fairgrounds.
How to find the best Pleasanton package deals?
Use Expedia's filter tool to help you find some unbeatable Pleasanton package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Pleasanton package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Pleasanton vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component individually. And you'll still have the freedom to create a tailored Pleasanton vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Pleasanton?
If you have your Pleasanton vacation dates confirmed, book as early as you can to snap up some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Pleasanton?

  1. Pick your travel dates: The things you want to do in Pleasanton and your favourite season will help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to cover everything from meals and transportation to flights and experiences. Your hotel will probably be the biggest expense during your trip to Pleasanton.
  3. Decide how many days away: Start by making a list of all the activities and attractions you want to get to in Pleasanton. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Pleasanton vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.