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

Top Holiday Package Deals in Roosevelt Park

Price found within the past 48 hours. Click for updated prices.
Aqua Breeze Inn

Aqua Breeze Inn

2.5 out of 5
Westside Santa Cruz
Price was CA $2,057, price is now CA $1,417 per person
CA $1,417
per person
Sep 6 - Sep 12
found 4 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to San Jose (SJC)
8.2/10 Very good! (1,009 reviews)

Motel 6 Santa Cruz, CA

Motel 6 Santa Cruz, CA

2 out of 5
Westside Santa Cruz
Price was CA $2,872, price is now CA $2,214 per person
CA $2,214
per person
Sep 6 - Sep 12
found 4 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to San Jose (SJC)
6/10 (649 reviews)

Marbellalane-4br Siliconvalley Gem 16min to Levi's

Marbellalane-4br Siliconvalley Gem 16min to Levi's

3 out of 5
Berryessa
Price was CA $3,500, price is now CA $2,701 per person
CA $2,701
per person
Aug 26 - Aug 30
found 9 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Jose (SJC)
No reviews

Marbella Lane Duplex San Jose 10-Min to Levi’s

Marbella Lane Duplex San Jose 10-Min to Levi’s

4 out of 5
Willow Glen
Price was CA $1,789, price is now CA $1,493 per person
CA $1,493
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Jose (SJC)
8.2/10 Very good! (15 reviews)
Thank you for giving my family the pleasure of staying in your home

Reviewed on May 21, 2026

La Bahia Hotel and Spa

La Bahia Hotel and Spa

4.5 out of 5
Westside Santa Cruz
Price was CA $3,223, price is now CA $2,691 per person
CA $2,691
per person
Sep 6 - Sep 12
found 4 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to San Jose (SJC)
9.6/10 Exceptional! (383 reviews)

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
A historic building with a clock tower, adjacent to a modern high-rise building.

Downtown San Jose

5 out of top 10 points of interest in this area

Known for its fascinating museums and great live music, there's plenty to explore in Downtown San Jose. You can visit top attractions like SAP Center at San Jose and San Pedro Square Market, 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

Sonesta Silicon Valley

Sonesta Silicon Valley

4 out of 5
1820 Barber Ln Milpitas CA
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Aug 2 to Aug 3
CA $147
CA $168 total
Aug 2 - Aug 3
includes taxes & fees
Sonesta Silicon Valley
Wild Palms, a JdV by Hyatt Hotel

Wild Palms, a JdV by Hyatt Hotel

3 out of 5
910 E Fremont Ave Sunnyvale CA
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Jul 31 to Aug 1
CA $131
CA $147 total
Jul 31 - Aug 1
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"Lobby and pool were cute. Pool and outside of property could use some TLC, getting somewhat rundown. Room was clean and had everything we needed. Breakfast was sufficient and convenient."

Reviewed on Jul 20, 2026

Wild Palms, a JdV by Hyatt Hotel
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 $130 per night from Aug 22 to Aug 23
CA $130
CA $147 total
Aug 22 - Aug 23
includes taxes & fees
9/10 Wonderful! (2,903 reviews)
"It was a very comfortable hotel to stay at. Lots of amenities, good breakfast, I felt very safe at the hotel and surroundings. The only thing was that my room wasn't cleaned during my 3 night stay. I do like to save water and so I didn't need my sheets or towels changed during my stay but it would ..."

Reviewed on Jul 21, 2026

Maple Tree Inn
See all 1,962 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
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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 CA $1,417. 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.

Things to do

LEGOLAND Discovery Center Bay Area

LEGOLAND Discovery Center Bay Area

CA $40
per adult
LEGOLAND Discovery Center Bay Area
Santa Cruz Redwoods Forest Therapy

Redwoods Forest Bathing

CA $169
per adult
Redwoods Forest Bathing
Niles History: An Audio Tour of the First Movie Capital

Niles History: An Audio Tour of the First Movie Capital

CA $14
per adult
Niles History: An Audio Tour of the First Movie Capital
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.