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Your Lakeside Vacation

With a Lakeside vacation package, say goodbye to travel planning and hello to an effortless adventure. Every detail of your journey has been taken care of before you depart, so you can make the most of your time discovering this exciting city. Fill your schedule with tours of Four Winds Casino New Buffalo, New Buffalo Public Beach and Warren Dunes State Park Beach, some of the attractions you shouldn't miss during a trip to Lakeside. Browse Expedia's wide range of travel options and start planning your dream vacation to Lakeside today.

The Latest Lakeside vacation packages

Price found within the past 48 hours. Click for updated prices.
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Discover the most popular places to visit in Lakeside

Lakeside Hotel Deals

1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More

1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More

Lakeside
9.2/10 Wonderful! (52 reviews)
"Great rental for multiple families. It was terrific having a pool and the beach was wonderful and close by."

Reviewed on Jul 30, 2025

1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
777 Blue Chip Drive, Michigan City, IN
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $148 total per night from Sep 1 to Sep 2
$148 total
Sep 1 - Sep 2
Total includes taxes and fees
8.2/10 Very Good! (1,652 reviews)
"Easy access to beach and boat race."

Reviewed on Aug 9, 2025

Blue Chip Casino Hotel and Spa
Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

3.5 out of 5
11111 Wilson Road, New Buffalo, MI
$131 nightly
The price is $138 total per night from Sep 2 to Sep 3
$138 total
Sep 2 - Sep 3
Total includes taxes and fees
9.2/10 Wonderful! (1,460 reviews)
"Copper Rock Steakhouse is very good! Been here before and it’s always good ."

Reviewed on Aug 9, 2025

Four Winds Casino Resort – New Buffalo
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.

Things to do near Lakeside

Lakeside, Michigan, is perfect for outdoor enthusiasts and those seeking a romantic getaway. Enjoy a variety of activities including lakefront and river vacations, lakeside adventures, and outdoor fun. Popular attractions feature a recreational area, playgrounds, and golf courses, making it an ideal destination for relaxation and adventure amidst beautiful scenery.

Shopping

Lakeside offers charming shopping experiences such as Round Barn Winery and Founders Wine Cellar, both 12 miles away, perfect for unique gifts. If you're up for a drive, Lighthouse Place Premium Outlets, located 15 miles away, features a variety of stores and entertainment options for the whole family.

Recreation

Weko Park offers serene nature trails perfect for relaxation and rejuvenation, located 8 miles from Lakeside. The Acorn, just 4 miles away, provides a cultural escape with engaging performances for family and romance. Galien River County Park, also 4 miles from Lakeside, invites you to unwind amidst beautiful landscapes.

Adventure

Experience thrilling fun at Captain Mike's Fun Park, an arcadeAdventureZone 7 miles from Lakeside. For adrenaline seekers, Red Bud Track-N-Trail offers exciting motorRacing 16 miles away. Don't miss the East Race Waterway, a waterSports venue 25 miles from Lakeside, perfect for outdoor adventures.

Nightlife

Experience vibrant nightlife in Lakeside with a visit to Round Barn Union Pier Tasting Room, just 1 mile away, offering romantic vibes. For a scenic option, check out Round Barn Baroda Tasting Room & Estate, 12 miles away, or Free Run Cellars, 14 miles away, both providing delightful atmospheres.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Lakeside

Lakeside, Michigan, is an idyllic destination for outdoor enthusiasts and romantic getaways, featuring beautiful beaches, serene lakes, and nearby state parks. Visitors can enjoy a variety of activities, from exploring lakeside destinations and relaxing at lake resorts to indulging in leisurely lake activities. With its stunning scenery and tranquil atmosphere, Lakeside offers the perfect backdrop for a memorable vacation experience.

  • Warren Dunes State Park: Just 6 miles from Lakeside, this stunning state park features towering sand dunes, scenic trails, and breathtaking views of Lake Michigan. Perfect for hiking, picnicking, and enjoying the great outdoors, it’s an adventure seeker’s paradise.
  • New Buffalo Public Beach: Located 5 miles away, this beautiful beach offers a relaxing atmosphere with soft sands and clear waters. Enjoy sunbathing, swimming, or beach volleyball while soaking in the sun and the vibrant local vibe.
  • Local: Also situated 5 miles from Lakeside, this attraction showcases the charm of the area, featuring unique shops, local art, and delightful eateries that reflect the community’s spirit and creativity.

Best time to go to Lakeside

The best time to visit Lakeside can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Lakeside falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Lakeside falls in January, visitor numbers are average and weather is mostly with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.8°F (-2.9°C)Light RainMostlyAverageSlightly Low
February27.9°F (-2.3°C)Light RainMostlyAverageAverage
March37.4°F (3.0°C)Light RainMostlyAverageSlightly Low
April46.4°F (8.0°C)Light RainMostly SunnyAverageAverage
May57.7°F (14.3°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnyModerately HighAverage
July72.3°F (22.4°C)Light RainMostly SunnyModerately HighSlightly High
August71.4°F (21.9°C)Light RainMostly SunnyModerately HighAverage
September65.8°F (18.8°C)Light RainMostly SunnyAverageSlightly High
October54.5°F (12.5°C)Light RainMostly SunnyModerately LowSlightly High
November42.3°F (5.7°C)Light RainMostly SunnyModerately LowAverage
December33.8°F (1.0°C)Light RainMostlyModerately LowSlightly Low

Tips to save on your trip to Lakeside

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Lakeside.
  • Consider traveling to Lakeside during the low season (March and December to January) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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Frequently asked questions

How much does a Lakeside vacation package cost?
Offering great value package deals from $249 on Expedia, you'll be pleasantly surprised at how much a vacation to Lakeside costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Lakeside?
If you'd like to score a cheap Lakeside vacation package, consider planning a trip in November, December and January. You're likely to find better prices on flights and accommodations during these months — perfect for a budget-friendly break.
How many days is enough for Lakeside?
With a well-planned itinerary, you can easily hit the main Lakeside sights in a handful of days. But if you prefer to explore off the beaten track or go on day tours, think about booking your Lakeside vacation for longer.
How to find the best Lakeside package deals?
Use Expedia's filters to find some great Lakeside package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Lakeside package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Lakeside vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Lakeside vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Lakeside?
Score 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 a spur-of-the-moment Lakeside break.
Does Expedia offer Book Now, Pay Later Lakeside vacation packages?
Your Lakeside getaway should be an escape from your busy life, not a source of money-related stress. So to allow you a bit more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.