Lakeside Vacations from $423

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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.
Riviera Oaks Resort

Riviera Oaks Resort

3 out of 5
San Diego Country Estates
Save 100% on your flight
Price was $665, price is now $423 per person
$423
per person
Jul 30 - Aug 4
found 23 hours ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
9.6/10 Exceptional! (1,005 reviews)
Great location and mi kiddos enjoy the pool a lot.

Reviewed on Jun 16, 2026

The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Save 100% on your flight
Price was $1,076, price is now $532 per person
$532
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Dallas (DAL) to San Diego (SAN)
8.6/10 Excellent! (2,204 reviews)
I was pleasantly surprised by how nicely kept and clean everything was, including carpets and furniture. The coffee in the room was great. The only negative is that there is no breakfast included and the adjacent restaurant to buy it does not open until 7:00 am. However, there is a Starbucks also next door. I highly recommend the room for the very good rate that I had.

Reviewed on Jun 16, 2026

Winners Circle Solana Beach Del Mar Resort

Winners Circle Solana Beach Del Mar Resort

2 out of 5
Save 100% on your flight
Price was $1,388, price is now $810 per person
$810
per person
Aug 18 - Aug 25
found 14 hours ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
9.4/10 Exceptional! (251 reviews)
Great location right across from the Del Mar racetrack. Lovely ambience.

Reviewed on Jun 16, 2026

Margaritaville Hotel San Diego Gaslamp Quarter

Margaritaville Hotel San Diego Gaslamp Quarter

4 out of 5
Downtown San Diego
Save 100% on your flight
Price was $1,550, price is now $921 per person
$921
per person
Aug 19 - Aug 23
found 20 hours ago
Roundtrip flight included
Dallas (DAL) to San Diego (SAN)
9/10 Wonderful! (1,384 reviews)
We had a wonderful time. Thank you.

Reviewed on Jun 16, 2026

Los Bungalows

Los Bungalows

2.5 out of 5
Save 100% on your flight
Price was $1,255, price is now $750 per person
$750
per person
Aug 27 - Aug 31
found 8 hours ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.2/10 Very Good! (536 reviews)
Honestly one of the best hotels I’ve stayed in the views the vibes overall very very peaceful place loved it

Reviewed on Jun 7, 2026

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Stay near popular Lakeside attractions

People fish from boats at Lake Jennings in Lakeside, California located in San Diego County also a popular destination for hiking, camping and picnicking.

Lake Jennings

9.0/5 (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.
See properties

Lakeside Hotel Deals

Manchester Grand Hyatt San Diego

Manchester Grand Hyatt San Diego

4 out of 5
1 Market Pl San Diego CA
Fully refundableReserve now, pay when you stay
$296 nightly
The price is $343 total per night from Jul 1 to Jul 2
$343 total
Jul 1 - Jul 2
Total with taxes and fees
9/10 Wonderful! (2,799 reviews)
"The service was poor at best. Valet didn’t take our bags. We waited for our car because valet was sitting and chit chatting. Hidden destination fees at check out. WiFi didn’t work. Not the 5 star experience they advertise."

Reviewed on Jun 16, 2026

Manchester Grand Hyatt San Diego
The Sofia Hotel

The Sofia Hotel

3.5 out of 5
150 W Broadway San Diego CA
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $186 total per night from Jun 28 to Jun 29
$186 total
Jun 28 - Jun 29
Total with taxes and fees
8.6/10 Excellent! (2,243 reviews)
"I was pleasantly surprised by how nicely kept and clean everything was, including carpets and furniture. The coffee in the room was great. The only negative is that there is no breakfast included and the adjacent restaurant to buy it does not open until 7:00 am. However, there is a Starbucks also ..."

Reviewed on Jun 16, 2026

The Sofia Hotel
Wyndham San Diego Bayside

Wyndham San Diego Bayside

4 out of 5
1355 N Harbor Drive San Diego CA
Fully refundableReserve now, pay when you stay
$182 nightly
The price is $211 total per night from Jun 29 to Jun 30
$211 total
Jun 29 - Jun 30
Total with taxes and fees
8.4/10 Very Good! (6,205 reviews)
"Great location. Rooms are a Lil dated but clean and well maintained."

Reviewed on Jun 16, 2026

Wyndham San Diego Bayside
See all 9,390 properties in Lakeside
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 $423 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?

  1. Pick your travel dates: What you want to do in Lakeside and your favorite season can help you decide when to go.
  2. 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.
  3. 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.
  4. 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.
  5. Bundle your accommodations and airfare: Once you've nailed down your dates and duration, book the ideal Lakeside vacation package for you.
  6. 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.

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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.