Glenwood 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*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Glenwood Vacation
Lock in a Glenwood vacation package that has everything you need and nothing you don't. Good for walking, cafes and dining, consider basing yourself in the neighborhood of Westside Santa Cruz. If a sightseeing tour is on the cards during your trip to Glenwood, visit leading attractions like Zip Line, Treks and Tracks Rock Climbing Trips and Valley Gardens Golf Course. Check out Expedia's wide range of travel options and start organizing your ideal vacation to Glenwood today.
Top Glenwood Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Fisherman's Wharf
Fisherman's Wharf
CA $1,156
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Francisco (SFO)
9/10 Wonderful! (7,683 reviews)
The place was clean and well kept grounds. The staff was friendly and welcoming. The location is prime within walking distance to Fisherman’s Wharf and North Beach.
Reviewed on Oct 25, 2026
Ready to book your vacation to Glenwood?
Glenwood Hotel Deals
La Bahia Hotel and Spa
215 Beach Street Santa Cruz CA
Fully refundableReserve now, pay when you stay
CA $452
CA $586 total
Oct 29 - Oct 30
includes taxes & fees
9.6/10 Exceptional! (578 reviews)
"Very nice place in excellent condition with excellent staff. My only critiques are that due to the design, there is little privacy for the rooms overlooking the pool. If you are on your balcony, you are on display for at least 75% of the other rooms. Also - the heated spa is located on a raised platform ..."
Reviewed on Oct 25, 2026
Holiday Inn San Jose - Silicon Valley by IHG
1350 N 1st Street San Jose CA
Fully refundable
CA $172
CA $202 total
Oct 30 - Oct 31
includes taxes & fees
8.4/10 Very good! (1,114 reviews)
"Amazing"
Reviewed on Oct 25, 2026
The Westin San Jose
302 South Market Street San Jose CA
Fully refundableReserve now, pay when you stay
CA $198
CA $239 total
Nov 8 - Nov 9
includes taxes & fees
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.
What to do in Glenwood
Beach Hill to Historic Downtown Santa Cruz Loop
CA $64
per adult
Santa Cruz Walking Tour: Discover Downtown & Mission Hill
CA $63
per adult
Capitola Friday Night Food Tour
CA $182
per adult
100% of travellers recommend
Frequently asked questions
How much does a Glenwood vacation package cost?
You can grab a vacation package to this destination from CA $1,156 on Expedia. However, how much your vacation to Glenwood costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Glenwood?
If you'd like to book a cheap Glenwood vacation package, consider visiting in January, February and November. You'll generally find better prices on airfares and hotels during these quieter months — perfect for a budget-friendly break.
How many days is enough for Glenwood?
The ideal duration of your Glenwood vacation depends on what you'd like to see and do. Typically, a few days to a week will give you plenty of time to visit all the leading attractions and explore some hidden spots along the way.
How to find the best Glenwood package deals?
Finding a cheap Glenwood package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can personalize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most affordable Glenwood package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Glenwood vacation as a package?
You can enjoy significant savings on your Glenwood escape by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to view the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Glenwood?
Score incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Glenwood escape.
How to plan a trip to Glenwood?
- Choose when to get away: Check your diary and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Glenwood.
- Set your budget: Consider costs like flights, transportation and food when calculating how much to set aside for your trip to Glenwood. Then, choose a hotel that matches your budget, whether that's an economical stay or a lavish getaway.
- Decide how long to go away for: Now that you're more familiar with Glenwood, you can work out the right length of your break. Create a rough plan and give yourself enough time to cover everything you want to see.
- Combine your accommodations and airfare: Once you've nailed down your trip dates and duration, book the right Glenwood vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
