Lakeside Vacations from $466

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

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.
The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Save 100% on your flight
Price was $1,091, price is now $466 per person
$466
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
8.6/10 Excellent! (2,321 reviews)
The hotel was amazing. The staff was less than helpful. They seem to expect that a QR code can replace human interaction. I normally expect a greeting along with a short brief on amenities and followed by "if you need anything please let us know". Instead I got. "Scan the QR code." The description of amenities was long and poorly written which required me, more than once to ask for clarification. When I check into a nice hotel after a long day of travel, I simply expect polite, welcoming and helpful. Not, get out your electronic device and figure it out.

Reviewed on Jul 13, 2026

Hyland Inn Near Legoland

Hyland Inn Near Legoland

3 out of 5
Olde Carlsbad
Save 100% on your flight
Price was $1,089, price is now $550 per person
$550
per person
Sep 26 - Oct 1
found 9 hours ago
Roundtrip flight included
New York (JFK) to San Diego (SAN)
7.8/10 Good! (1,007 reviews)
Friendly staff!!!

Reviewed on Jul 13, 2026

Paradise Point Resort & Spa

Paradise Point Resort & Spa

4 out of 5
Mission Bay
Save 100% on your flight
Price was $1,305, price is now $755 per person
$755
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) to San Diego (SAN)
8.8/10 Excellent! (2,684 reviews)
Gorgeous resort! Big rooms that are clean and comfortable. Staff was excellent and went above and beyond to make my Birthday special! Landscaping and wildlife make this place feel like you’re in your own oasis. Bay access provides for tons of activities. Definitely planning on coming back

Reviewed on Jul 13, 2026

Hotel Z

Hotel Z

3 out of 5
Downtown San Diego
Save 100% on your flight
Price was $1,021, price is now $620 per person
$620
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
9.4/10 Exceptional! (1,031 reviews)
The card I was given when I checked in said there would be something to eat/drink in the lobby during the afternoon. There was nothing. Also I expected some kind of breakfast, but there was only coffee.

Reviewed on Jul 12, 2026

WorldMark Oceanside

WorldMark Oceanside

3 out of 5
Camp Pendleton South
Save 100% on your flight
Price was $972, price is now $595 per person
$595
per person
Aug 21 - Aug 24
found 13 hours ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.8/10 Excellent! (52 reviews)
Property and staff were GREAT!!!

Reviewed on Jun 2, 2026

Don't see what you're looking for?
See all available trips from Columbus to Lakeside
View all trips

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
See all activities in Lakeside

Lakeside Hotel Deals

Paradise Point Resort & Spa

Paradise Point Resort & Spa

4 out of 5
1404 Vacation Rd San Diego CA
Fully refundableReserve now, pay when you stay
$325 nightly
The price is $374 total per night from Aug 9 to Aug 10
$374 total
Aug 9 - Aug 10
Total with taxes and fees
8.8/10 Excellent! (2,739 reviews)
"Gorgeous resort! Big rooms that are clean and comfortable. Staff was excellent and went above and beyond to make my Birthday special! Landscaping and wildlife make this place feel like you’re in your own oasis. Bay access provides for tons of activities. Definitely planning on coming back"

Reviewed on Jul 13, 2026

Paradise Point Resort & Spa
Wyndham San Diego Bayside

Wyndham San Diego Bayside

4 out of 5
1355 N Harbor Drive San Diego CA
$167 nightly
The price is $194 total per night from Aug 3 to Aug 4
$194 total
Aug 3 - Aug 4
Total with taxes and fees
8.4/10 Very Good! (6,212 reviews)
"Best place for kiddos and wife!!!"

Reviewed on Jul 13, 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
$248 nightly
The price is $287 total per night from Jul 19 to Jul 20
$287 total
Jul 19 - Jul 20
Total with taxes and fees
9/10 Wonderful! (4,056 reviews)
"Very disappointing stay. Will not be staying with Hard Rock again. Room was on the 4th floor and looked directly into the parking garage. Hotel seems dated and staff was not friendly, helpful or welcoming. Was barely acknowledged at Check In. Zero smile, greeting or conversation about hotel amenities ..."

Reviewed on Jul 13, 2026

Hard Rock Hotel San Diego
See all 9,340 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Lakeside vacation package cost?
You can pick up a vacation package to this top destination from $466 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.