Lakeside Vacations from $518

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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.
The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Save 100% on your flight
Price was $1,056, price is now $518 per person
$518
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Chicago (CHI) to San Diego (SAN)
8.6/10 Excellent! (2,287 reviews)
The hotel itself was fine, but our experience at the uca restaurant was terrible. The restaurant seemed severely short-staffed, service was very slow, and we waited a long time for our food. Unfortunately, the food quality was also very poor. This experience left a negative impression and overshadowed the rest of our stay.

Reviewed on Jun 25, 2026

Murrieta Hot Springs Resort

Murrieta Hot Springs Resort

4 out of 5
Murrieta Hot Springs
Save 100% on your flight
Price was $1,460, price is now $914 per person
$914
per person
Sep 11 - Sep 17
found 6 hours ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.6/10 Excellent! (580 reviews)
Staff members were helpful.

Reviewed on Jun 23, 2026

Los Bungalows

Los Bungalows

2.5 out of 5
Save 100% on your flight
Price was $1,061, price is now $667 per person
$667
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
8.2/10 Very Good! (538 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

Shore House at The Del, LXR Hotels & Resorts

Shore House at The Del, LXR Hotels & Resorts

5 out of 5
Historic Downtown Coronado
Save 100% on your flight
Price was $2,219, price is now $1,423 per person
$1,423
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
9.2/10 Wonderful! (159 reviews)
One of my best vacations! This is definitely a must visit property again and again!

Reviewed on Jun 15, 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 $1,293, price is now $829 per person
$829
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Chicago (CHI) to San Diego (SAN)
9/10 Wonderful! (1,404 reviews)
The Property has a great Manager and very pleasant staff.

Reviewed on Jun 24, 2026

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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

9.0/5 (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

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
Wine Tour Private San Diego County

Wine Tour Private San Diego County

$595
per traveler
Wine Tour Private San Diego County
See all activities in Lakeside

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 6 to Jul 7
$343 total
Jul 6 - Jul 7
Total with taxes and fees
9/10 Wonderful! (2,776 reviews)
"I highly recommend staying here excellent experience!"

Reviewed on Jun 25, 2026

Manchester Grand Hyatt San Diego
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
$180 nightly
The price is $209 total per night from Jul 1 to Jul 2
$209 total
Jul 1 - Jul 2
Total with taxes and fees
8.4/10 Very Good! (6,223 reviews)
"Other than the rooms being a little bit dated (just kinda older stuff) everything was fantastic. We stayed in tower 3 floor 11 and I have to say the views were amazing!! If you get the chance to use the west(glass) elevator do it about 45 minutes before sunset and go up haha the view is stunning!!! ..."

Reviewed on Jun 26, 2026

Wyndham San Diego Bayside
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
$317 nightly
The price is $364 total per night from Jul 1 to Jul 2
$364 total
Jul 1 - Jul 2
Total with taxes and fees
8.8/10 Excellent! (2,666 reviews)
"Beautiful property. Room was very clean, very nice; but did have a few maintenance issues. Love that we could stay a day of check out until 10 o’clock and use the property and all the pools and hot tubs, but wish the pools were open later during our stay (all close at 10)."

Reviewed on Jun 26, 2026

Paradise Point Resort & Spa
See all 9,413 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 $518 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.