Lakeside Vacations from $342
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Your Lakeside Vacation
Reserve a Lakeside vacation package and get ready to experience the best of this lively city. Consider staying in the neighborhood of Lake Murray, which is good for golfing, views and families. The Magnolia, Santee Lakes and Shadow Mountain Community Church are just a few of the sights worth visiting during your trip to Lakeside. Stop dreaming and start traveling. Check out the many options on Expedia today and finally put your Lakeside vacation plans into motion!
The Latest Lakeside vacation packages
Price found within the past 48 hours. Click for updated prices.
Legacy Resort Hotel & Spa
Mission Valley
$494
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
9.2/10 Wonderful! (3,115 reviews)
Property is very nice, room and bathroom were clean. TV and wifi would disconnect every 3-5 mins, the safe had an error and would not lock, our key cards failed last night and maintenance needed to replace the door batteries...they graciously refunded our parking fees.
We didn't know this Legacy hotel was a religious property. Small clues like the psalms on kiosks throughout the grounds and the "heavenly" soaps 🙏🤔
Reviewed on Sep 27, 2026
Stay near popular Lakeside attractions
Lake Jennings
9.0/10 (2 reviews)
This serene reservoir offers premier trout and catfish fishing in San Diego County's picturesque hills. Rent a motorboat to explore hidden coves or camp overnight with panoramic lake views.
Photo by Gerard Nastor
Barona Creek Golf Club
10.0/10 (1 review)
Barona Creek Golf Club blends perfectly with San Diego's rolling foothills, ranking among top casino courses nationwide. Enjoy its meticulously maintained fairways amid tranquil native vegetation and scenic vistas.
Barona Casino
9.2/10 (11 reviews)
This expansive resort boasts over 2,500 slot machines and a championship golf course in scenic Barona Valley. Reserve a table at one of the award-winning restaurants for a refined break between gaming sessions.
What to do in Lakeside
Chauffeured Adventure to Local San Diego Vineyards
$209
per adult
100% of travellers recommend
Lakeside Hotel Deals
Paradise Point Resort & Spa
1404 Vacation Rd San Diego CA
Fully refundableReserve now, pay when you stay
$245 nightly
$282 total
Oct 25 - Oct 26
Total with taxes and fees
8.8/10 Excellent! (2,902 reviews)
"Hard to connect to the guest wifi, no sanitary wipes to wipe down the gym equipment after use. Amenities and parking should be included with the stay. Staff was very friendly, polite and willing to assist"
Reviewed on Sep 28, 2026
Best Western Seven Seas
411 Hotel Circle South San Diego CA
Fully refundableReserve now, pay when you stay
$85 nightly
$97 total
Sep 29 - Sep 30
Total with taxes and fees
7.8/10 Good! (3,945 reviews)
"Convenient to have a small cafe on premises along with a bar Need to supply towels by the pool and spa areas so you don’t have to bring towels from room."
Reviewed on Sep 27, 2026
Wyndham San Diego Bayside
1355 N Harbor Drive San Diego CA
Fully refundableReserve now, pay when you stay
$182 nightly
$211 total
Oct 25 - Oct 26
Total with taxes and fees
8.4/10 Very Good! (6,338 reviews)
"Very good location, check in was fast but not informative regarding parking or location of towers, basic informati on was provided. Receptionist that checked me in was not friendly, seemed like she disliked her job."
Reviewed on Sep 28, 2026
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 Lakeside Vacation Packages
Lakeside Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | San Diego Intl. Airport (SAN) |
Population | 20,600 |
Max Temp Winter | 65ºF |
Max Temp Summer | 85ºF |
Top Sights | Salerno Winery, Boomers El Cajon and Creation and Earth History Museum |
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Frequently asked questions
How much does a Lakeside vacation package cost?
You can pick up a vacation package to this top destination from $342 on Expedia. But how much your vacation to Lakeside costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Lakeside?
September, October and December are great times to look for cheap Lakeside vacation packages. Opting to travel in quieter periods means you can typically find reduced prices on flights and accommodations.
How many days is enough for Lakeside?
With a well-planned schedule, you can easily hit the main Lakeside sights in a handful of days. But if you prefer to discover hidden gems or take day trips, consider booking your Lakeside vacation for longer.
How to find the best Lakeside package deals?
Begin your search for a Lakeside package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Lakeside package deal right away, simply 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 Lakeside escape off to a flying start.
Is it cheaper to book a Lakeside vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Lakeside vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Lakeside?
Enjoy amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Lakeside escape.
How to plan a trip to Lakeside?
- Pick your travel dates: What you want to do in Lakeside and your favorite season can help you decide when to go.
- Plan your budget wisely: Besides the price of your hotel, you should factor in other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to Lakeside.
- Discover Lakeside using our trip planning tool: Gain insights into the top attractions and best properties for your trip to Lakeside. You can also save your favorite places, collaborate with friends and family and organize your plans in one place.
- Decide how long to go away for: Now that you're up to speed on Lakeside, you can work out the right length of your vacation. Create a draft itinerary and give yourself enough time to cover everything you want to see.
- Bundle your accommodations and airfare: Once you've nailed down your dates and duration, book the ideal Lakeside vacation package for you.
- Add on excursions and experiences: Take a look at our travel guide to find some exciting things to do in Lakeside. Book tickets or make reservations in advance to save time and avoid the stress of searching for activities once you arrive.
Does Expedia offer Book Now, Pay Later Lakeside vacation packages?
Secure your perfect escape to Lakeside with our Book Now, Pay Later vacations. No need to scrimp and save or hold off until the next payday — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stay on budget and snag great deals before they disappear.
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
