Lakeside Vacations from $330

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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.
Hyland Inn Near Legoland

Hyland Inn Near Legoland

3 out of 5
Olde Carlsbad
Save 100% on your flight
Price was $522, price is now $330 per person
$330
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
7.8/10 Good! (1,030 reviews)

Pantai Inn

Pantai Inn

3.5 out of 5
Village of La Jolla
Price was $1,712, price is now $956 per person
$956
per person
Jan 7 - Jan 11
found 2 hours ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
9.4/10 Exceptional! (1,002 reviews)

Ocean Villas of Carlsbad

Ocean Villas of Carlsbad

3 out of 5
Carlsbad Village
Save 100% on your flight
Price was $1,930, price is now $1,103 per person
$1,103
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Seattle (SEA) to San Diego (SAN)
9.2/10 Wonderful! (25 reviews)
This is a very cute place.

Reviewed on Oct 24, 2026

Guesthouse Hotel at La Valle

Guesthouse Hotel at La Valle

4.5 out of 5
Save 100% on your flight
Price was $754, price is now $432 per person
$432
per person
Jan 7 - Jan 11
found 2 hours ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
9.2/10 Wonderful! (269 reviews)
Loved the property, great amenities, beautiful room and VERY comfortable bed and pillows. The front desk staff seemed to be quite new and not terribly well informed but I imagine that was unusual. I would definitely stay here again.

Reviewed on Oct 29, 2026

The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Price was $1,011, price is now $614 per person
$614
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Chicago (CHI) to San Diego (SAN)
8.8/10 Excellent! (2,743 reviews)

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Stay near popular Lakeside attractions

A calm lake with a boat, surrounded by lush greenery and mountains in the background.

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.
See properties

What to do in Lakeside

Wine tours perfect for bachelorettes

Chauffeured Adventure to Local San Diego Vineyards

$246
per adult
100% of travellers recommend
Chauffeured Adventure to Local San Diego Vineyards
San Diego: Guided Natural History Walk

San Diego: Guided Natural History Walk

$64
per adult
San Diego: Guided Natural History Walk
Wine Tour Private San Diego County

Wine Tour Private San Diego County

$699
per traveler
Wine Tour Private San Diego County
See all activities in Lakeside

Lakeside Hotel Deals

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 Nov 1 to Nov 2
$211 total
Nov 1 - Nov 2
Total with taxes and fees
8.4/10 Very Good! (6,344 reviews)
"Nice clean room, central located to walking activities. It's nice to have a view of the bay but not nice to look onto the dirty roof tops of the buildings in front of us. That I do not know if they can do anything about. On a nicer note we spoke with a lovely lady about different eating places we ..."

Reviewed on Oct 28, 2026

Wyndham San Diego Bayside
Hard Rock Hotel San Diego

Hard Rock Hotel San Diego

4 out of 5
207 5th Ave San Diego CA
Fully refundableReserve now, pay when you stay
$211 nightly
The price is $244 total per night from Nov 22 to Nov 23
$244 total
Nov 22 - Nov 23
Total with taxes and fees
9/10 Wonderful! (4,562 reviews)
"Had trouble with my key during the stay it was very unpleasant going twice up and down to the lobby. On top of that the bed was dirty underneath."

Reviewed on Oct 28, 2026

Hard Rock Hotel San Diego
Handlery Hotel

Handlery Hotel

3.5 out of 5
950 Hotel Cir N San Diego CA
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $101 total per night from Nov 29 to Nov 30
$101 total
Nov 29 - Nov 30
Total with taxes and fees
Handlery Hotel
See all 9,535 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 $330 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.