Roosevelt Park 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
Price found within the past 48 hours. Click for updated prices.
  • Property grounds
    Jun 25 - Jun 26

    Sonesta Silicon Valley + Flight

    Milpitas
    1 night
    4.0 star property
    9.0/10 - Wonderful (1,947 reviews)
    "Clean rooms, was happy to hear that I got an upgrade to a suite! Loved the suite. The pool and jacuzzi was clean, enjoyed the drinks at the bar and the wings were fire! Had a great stay there!"
    Reviewed May 24, 2026
    Roundtrip • Vancouver (YVR) - San Jose (SJC)
    YVR - SJC • 1 stop SJC - YVR • 1 stop
    CA $1,126
    CA $919
    per traveller
    found 1 day ago
    Sonesta Silicon Valley
  • Poolside bar
    Aug 5 - Aug 9

    Shashi Hotel Mountain View Palo Alto + Flight

    Mountain View
    4 nights
    5.0 star property
    9.4/10 - Exceptional (1,387 reviews)
    "Wonderful. We only stayed one night but it was great. Parking garage was easy to navigate. Multiple food options in the hotel. Staff was very friendly and gave a complimentary drink upon check in. Would recommend."
    Reviewed May 23, 2026
    Roundtrip • Vancouver (YVR) - San Jose (SJC)
    YVR - SJC • 1 stop SJC - YVR • 1 stop
    CA $1,962
    CA $1,428
    per traveller
    found 1 day ago
    Shashi Hotel Mountain View Palo Alto
  • Lobby
    Aug 5 - Aug 9

    Avatar Hotel Santa Clara, Tapestry Collection by Hilton + Flight

    Santa Clara
    4 nights
    3.5 star property
    8.8/10 - Excellent (284 reviews)
    Roundtrip • Vancouver (YVR) - San Jose (SJC)
    YVR - SJC • 1 stop SJC - YVR • 1 stop
    CA $1,479
    CA $1,163
    per traveller
    found 1 day ago
    Avatar Hotel Santa Clara, Tapestry Collection by Hilton
  • Interior
    Aug 5 - Aug 9

    Aloft by Marriott San Jose Cupertino + Flight

    West San Jose
    4 nights
    3.0 star property
    9.0/10 - Wonderful (1,001 reviews)
    "Clean, quiet and close to several restaurants. "
    Reviewed May 18, 2026
    Roundtrip • Vancouver (YVR) - San Jose (SJC)
    YVR - SJC • 1 stop SJC - YVR • 1 stop
    CA $1,265
    CA $1,028
    per traveller
    found 1 day ago
    Aloft by Marriott San Jose Cupertino
  • Property entrance
    Aug 5 - Aug 9

    Larkspur Landing Extended Stay Suites Milpitas + Flight

    Milpitas
    4 nights
    3.0 star property
    7.8/10 - Good (1,002 reviews)
    "The property was very clean. I also enjoyed the breakfast."
    Reviewed May 21, 2026
    Roundtrip • Vancouver (YVR) - San Jose (SJC)
    YVR - SJC • 1 stop SJC - YVR • 1 stop
    CA $1,140
    CA $962
    per traveller
    found 1 day ago
    Larkspur Landing Extended Stay Suites Milpitas

Where to stay in Roosevelt Park

Find the best Roosevelt Park areas and neighborhoods for the activities you enjoy most. Learn more about Roosevelt Park
Downtown San Jose

Downtown San Jose

5 out of top 10 points of interest in this area
4.5/5(31 area reviews)

Known for its fascinating museums and great live music, there's plenty to explore in Downtown San Jose. You can visit top attractions like San Pedro Square and Plaza de Cesar Chavez, and jump on the metro at Santa Clara Station or St James Station to see more of the city.

Find hotels in Downtown San Jose

Roosevelt Park Hotel Deals

Maple Tree Inn

Maple Tree Inn

3 out of 5
711 E El Camino Real Sunnyvale CA
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from May 29 to May 30
CA $140
CA $158 total
May 29 - May 30
includes taxes & fees
9/10 Wonderful! (2,756 reviews)
"Delicious Breakfast! Friendly and Fantastic Staff! Would definitely stay here again! Great Job!!"

Reviewed on May 24, 2026

Maple Tree Inn
Hyatt Place San Jose Airport

Hyatt Place San Jose Airport

3 out of 5
82 Karina Court, Airport San Jose CA
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Jun 7 to Jun 8
CA $163
CA $188 total
Jun 7 - Jun 8
includes taxes & fees
9/10 Wonderful! (1,582 reviews)
"Good location, nice hotel"

Reviewed on May 24, 2026

Hyatt Place San Jose Airport
Dinah's Garden Hotel

Dinah's Garden Hotel

3.5 out of 5
4261 El Camino Real Palo Alto CA
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from May 29 to May 30
CA $186
CA $215 total
May 29 - May 30
includes taxes & fees
9.6/10 Exceptional! (1,004 reviews)
"I loved the unique outside of the hotel. Was very beautiful. Parking was good. Had a restaurant and pool and gym. Our stay was quick and just over night so we didn't use the amenities so I can't say how they were. The fridge had drinks to purchase at reasonable price. Was a quick easy check in. My ..."

Reviewed on May 23, 2026

Dinah's Garden Hotel
See all 1,974 properties in Roosevelt Park
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 a Roosevelt Park vacation package cost?
We make it simple to travel the world, with Roosevelt Park vacation packages starting from just . You'll have the flexibility to combine your preferred hotels, airlines and car rental. For the ultimate getaway, why not add a few experiences and tours to your travel itinerary?
How do I get a cheap travel package to Roosevelt Park?
Think of all the fun things you could do in Roosevelt Park with a wad of extra cash in your wallet. Watch your savings stack up when you combine your flights, hotels and other bookings into a Roosevelt Park vacation package. You have loads of choice when you book your trip with Expedia too. In fact, you can choose from more than 550 airlines and 1,000,000 hotel options around the globe. Whether you're vacationing with the whole family or traveling with someone special, organizing a trip to Roosevelt Park is better with a package.
Where should I stay in Roosevelt Park?
Visitors come from all over to experience Winchester Mystery House and San Jose Convention Center in Roosevelt Park. Stay within a stone's throw of these must-see attractions and visit them whenever you want.
How far in advance should I book my Roosevelt Park vacation?
Be rewarded with the biggest variety at the cheapest prices by booking your Roosevelt Park adventure nice and early. Air carriers usually release tickets around a year prior to departure, so start your planning ASAP. Having said that, Expedia is committed to providing you with the best bargains around, so it's always a good time to book your dream vacation!
What does an Expedia Roosevelt Park travel package include?
Flights, car rentals and hotels — we bring you the very best deals. All you have to do is pick and choose your preferred combination. After you've made your booking, you can add on the fun stuff like day tours and sightseeing activities. Our travel packages make it simple to create an exciting Roosevelt Park getaway.
What should I know before booking a Roosevelt Park travel package?
Find deals to suit your budget with an Expedia package. Flights, hotels, rental cars — we have everything you need to plan your escape. You'll save a tidy sum just for bundling your bookings. Whether you're taking off on an adventure in the snow or relaxing on a sunny beach, your ideal vacation is just clicks away.
Can I choose my airline with a Roosevelt Park Expedia vacation package?
Most definitely. Expedia has over 550 partner airlines to select from worldwide. With such a big range of choice, finding the perfect carrier to bring you to Roosevelt Park will be a cinch.
If I'm not able to travel, can I cancel my Roosevelt Park vacation package?
Your situation can change unexpectedly, so yes. You may be able to change or cancel your Roosevelt Park vacation package for free within 24 hours of booking. For older bookings, you can still cancel and rebook, but your car rental company, hotel or airline may impose a charge. Looking for more information? Visit our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Roosevelt Park

Santana Row Shopping Center

Santana Row Shopping Center

During your trip to San Jose, you can enjoy retail therapy at Santana Row Shopping Center. Attend a sporting event or discover the mountain views in this family-friendly area.

Santana Row Shopping Center
Winchester Mystery House

Winchester Mystery House

Wonder about the alleged hauntings and other mysteries as you chart the life of a gun magnate’s widow in this unfinished manor.

Winchester Mystery House
Raging Waters

Raging Waters

Bring your family to Raging Waters and enjoy some excitement at this theme park in San Jose. Discover the top-notch restaurants and great live music in this family-friendly area.

Raging Waters

Things to do

LEGOLAND Discovery Center Bay Area

LEGOLAND Discovery Center Bay Area

CA $38
per adult
LEGOLAND Discovery Center Bay Area
Picture 2 for Activity San Jose: Valley Ghosts Haunted Walking Tour

San Jose Ghost Tour: The Scythe, Sacrifice, & Silhouette

CA $44
per adult
San Jose Ghost Tour: The Scythe, Sacrifice, & Silhouette
Special Ops: Mysterious Market

The Escape Game San Jose: Epic 60-Minute Adventure at Valley Fair

CA $64
per adult
The Escape Game San Jose: Epic 60-Minute Adventure at Valley Fair
See all activities in San Jose
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.