Pleasanton Vacations from $405

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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.

The Latest Pleasanton vacation packages

Price found within the past 48 hours. Click for updated prices.
WorldMark Windsor

WorldMark Windsor

3 out of 5
Save 100% on your flight
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
9/10 Wonderful! (328 reviews)
Loved this property! Stayed with my Fiance! Great for family ❤️ Only wished the hot tubs were fixed & WiFi should be free 😊 other than that, great stay. Staffs were very accommodative and informative. We had Dante that introduced us to the nearby restaurants and what to do around the area. Greatly appreciated.

Reviewed on Apr 27, 2025

River Terrace Inn - A Noble House Hotel

River Terrace Inn - A Noble House Hotel

4 out of 5
Downtown Napa
Save 100% on your flight
per person
Sep 19 - Sep 23
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Oakland (OAK)
9/10 Wonderful! (1,002 reviews)
We enjoyed this property for the most part. I expected the restaurant in the hotel to feel more like a traditional restaurant, but it often felt empty, like no one was really there eating or serving. They also stop serving food at 10am, don’t start again until 4pm, and close at 10pm. It’s not a big deal since there’s a great spot to eat just 5 minutes away and plenty of options within a short drive. My only other complaint is that our room wasn’t cleaned some days, or if it was, it happened very late, one of my pet peeves. That said, the room itself was nice, and sitting by the river was absolutely wonderful.

Reviewed on Jul 8, 2025

RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort

3 out of 5
Stonehouse
Save 100% on your flight
per person
Sep 19 - Sep 23
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Oakland (OAK)
8.6/10 Excellent! (1,266 reviews)
Was a good size and decent price. Would stay again.

Reviewed on Jul 9, 2025

MacArthur Place Hotel & Spa

MacArthur Place Hotel & Spa

4 out of 5
Save 100% on your flight
per person
Sep 19 - Sep 23
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Oakland (OAK)
9.4/10 Exceptional! (818 reviews)
was like paradise's

Reviewed on Jul 9, 2025

Hotel Yountville

Hotel Yountville

4 out of 5
Save 100% on your flight
per person
Sep 19 - Sep 23
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Oakland (OAK)
9.6/10 Exceptional! (999 reviews)
Stayed here for our anniversary. Our room

Reviewed on Jun 30, 2025

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Discover the most popular places to visit in Pleasanton

Best Turkey Legs I've ever had at the Alameda County Fair in Pleasanton, CA.

Alameda County Fairgrounds

3.5/5(13 reviews)

Enjoy a round of golf in Pleasanton at Alameda County Fairgrounds. Attend a sporting event in this family-friendly area.

Alameda County Fairgrounds

Stoneridge Shopping Center

4/5(43 reviews)

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

Ruby Hill Winery

3.5/5(4 reviews)

You can enjoy a tasting or tour at Ruby Hill Winery during your travels to Pleasanton. Attend a sporting event in this family-friendly area.

Ruby Hill Winery

What to do in Pleasanton

San Francisco: Airplane Bay Tour

San Francisco: Airplane Private Bay Tour

$289
per adult
100% of travellers recommend
San Francisco: Airplane Private Bay Tour
Napa Valley: Airplane Napa Valley Tour

Napa Valley: Airplane Napa Valley Tour

$319
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

$100
per adult
4 Hour Livermore Valley Wine Tour
See all activities in Pleasanton

Pleasanton Hotel Deals

Hyatt Centric Santa Clara Silicon Valley

Hyatt Centric Santa Clara Silicon Valley

3.5 out of 5
3100 Lakeside Dr, Santa Clara, CA
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $159 total per night from Jul 25 to Jul 26
$159 total
Jul 25 - Jul 26
Total includes taxes and fees
8.8/10 Excellent! (1,017 reviews)
"Really nice area! Hotel staff was extremly friendly and room was perfect for my family."

Reviewed on Jul 13, 2025

Hyatt Centric Santa Clara Silicon Valley
The Marina Inn on San Francisco Bay

The Marina Inn on San Francisco Bay

2.5 out of 5
68 Monarch Bay Dr, San Leandro, CA
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $110 total per night from Jul 20 to Jul 21
$110 total
Jul 20 - Jul 21
Total includes taxes and fees
8.4/10 Very Good! (1,997 reviews)
"."

Reviewed on Jul 12, 2025

The Marina Inn on San Francisco Bay
Sonesta Silicon Valley

Sonesta Silicon Valley

4 out of 5
1820 Barber Ln, Milpitas, CA
Fully refundable
$110 nightly
The price is $125 total per night from Jul 25 to Jul 26
$125 total
Jul 25 - Jul 26
Total includes taxes and fees
9/10 Wonderful! (1,522 reviews)
"Large modern room"

Reviewed on Jul 15, 2025

Sonesta Silicon Valley
See all 2,515 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.

Find the Best Pleasanton Vacation Packages

Pleasanton Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norman Y. Mineta San Jose Intl. Airport (SJC)
Population
79,500
Max Temp Winter
60ºF
Max Temp Summer
85ºF
Top Sights
Ruby Hill Winery, Aqua Adventure Water Park and Tesla Vintners

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Frequently asked questions

How much does a Pleasanton vacation package cost?
You'll find cheap prices from $405 on Expedia for your Pleasanton break. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Pleasanton costs.
What are the cheapest months to go to Pleasanton?
You can generally find lower rates and better availability in January, August and October. Take a look at our cheap Pleasanton vacation packages and you could land some great off-season deals.
How many days is enough for Pleasanton?
The ideal length of your Pleasanton vacation depends on what you'd like to do. Usually, a few days to a week will give you time to hit all the top sights and explore some hidden treasures along the way.
Is it worth booking a vacation package to Pleasanton?
Pleasanton has everything you need for an unforgettable escape. Get your Pleasanton vacation off to a flying start by exploring top attractions like Alameda County Fairgrounds.
How to find the best Pleasanton package deals?
Begin your search for a Pleasanton package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Pleasanton package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Pleasanton adventure underway.
Is it cheaper to book a Pleasanton vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still get the freedom to create a customized Pleasanton vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Pleasanton?
If you're planning a spontaneous Pleasanton adventure, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Pleasanton?

  1. Choose the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to go to Pleasanton.
  2. Set a budget: Consider costs like food, flights and transportation when working out how much to save for your trip to Pleasanton. Then, pick a property that works with your budget, whether that's a low-cost option or a lavish getaway.
  3. Discover Pleasanton with Expedia's trip planning tool: Gain insights into the top attractions and best hotels for your trip to Pleasanton. You can also save your must-visit places, collaborate with family and friends and manage your plans in one place.
  4. Determine how many days away: Start by listing all the attractions and activities you'd like to experience in Pleasanton. Then, estimate how long you'll need for each, including any travel time.
  5. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored Pleasanton vacation package.
  6. Book any day trips or activities: Now to the fun part --- locking in everything you want to see and do. Check out some of the top things to do in Pleasanton and book your tickets early to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Pleasanton vacation packages?
Jet off on your dream getaway to Pleasanton with Expedia's Book Now, Pay Later vacations. There's no need to save up or hold off until the next payday --- we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily stay on budget and snag great deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.