Lakeside vacation rentals

We found 862 vacation rentals — enter your dates for availability

Select from 45 homes, 23 cottages, and other vacation rentals in Lakeside to find one that's perfect for your trip. Vacation rentals provide the amenities you need and want for your family, friends, or furry companion, like WiFi and cable TV. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Lakeside

Showing deals for:Dec 12 - Dec 19

Image gallery for Beach house with Private Heated Pool, Jacuzzi, Firepit. Steps to beach and park.

Pool
9.4 out of 10 rating
Exceptional
(12 reviews)

Beach house with Private Heated Pool, Jacuzzi, Firepit. Steps to beach and park.

New Buffalo, MI

17% off
Price is $500
$3,503 for 7 nights
All fees included
Beach house with Private Heated Pool, Jacuzzi, Firepit. Steps to beach and park.

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Find out more about Lakeside

Find out more about Lakeside

Why visit Lakeside

  • Stunning Beaches: Enjoy beautiful sandy beaches perfect for sunbathing, swimming, and relaxation.
  • Scenic Lakefront Estates: Explore picturesque lakefront properties that offer breathtaking views and tranquil surroundings.
  • Outdoor Activities: Engage in various outdoor pursuits such as hiking, fishing, and boating in nearby national parks.
  • Charming Accommodations: Choose from inviting vacation homes, cozy cottages, and comfortable apartments for a memorable stay.
  • Family-Friendly Fun: Discover a blend of activities suitable for families, ensuring an enjoyable experience for all ages.

Popular types of accommodation in Lakeside

If you're considering a getaway to Lakeside, you're in for a treat. Our most popular accommodation options include inviting Houses, charming Cottages, and cozy Apartments. Whether you're searching for lakefront vacation homes or Michigan vacation rentals, we've got a variety of choices to suit your needs. Enjoy your stay with the comfort and tranquility that only Lakeside can offer.

  • Houses: The top choice for visitors, offering spacious and comfortable living spaces ideal for families or groups.
  • Cottages: A charming option, often providing a cozy atmosphere and a touch of rustic appeal near the lake.
  • Apartments: A convenient choice for travelers seeking modern amenities and proximity to local attractions.
  • Condos: A popular option featuring resort-like amenities and great views, perfect for a relaxing getaway.
  • Cabins: A favored retreat for nature lovers, offering a unique experience in a tranquil setting.**

Top attractions near Lakeside

Lakeside, Michigan, offers a perfect getaway for outdoor enthusiasts and romance seekers alike. With its stunning beaches, serene lakes, and nearby national parks, visitors can immerse themselves in breathtaking scenery. Ideal for family vacations or a relaxing retreat, Lakeside provides plenty of vacation ideas and activities to enjoy the great outdoors. Whether you're looking to unwind or explore, this charming destination has something for everyone.

  • Warren Dunes State Park: A stunning natural retreat featuring towering sand dunes, lush forests, and scenic views of Lake Michigan. Perfect for hiking, picnicking, and enjoying the great outdoors.
  • New Buffalo Public Beach: A beautiful sandy beach ideal for sunbathing, swimming, and beach volleyball. Enjoy a relaxing day by the water with family and friends.
  • Local: A charming attraction that showcases the unique culture and community spirit of the area, offering a variety of shops, eateries, and local events.

Things to do recommended for couples

For a romantic escape in Lakeside, indulge in wine tasting at St. Julian Winery, just a mile away, or explore Hickory Creek Winery and Chill Hill Winery, both offering enchanting vibes. Savor the local flavors and create unforgettable memories together amidst beautiful surroundings.

Things to do recommended for families

Families visiting Lakeside can enjoy outdoor adventures at Weko Park, Galien River County Park, and Turtle Creek Preserve, each offering wellness and relaxation vibes just a short drive away. These parks are perfect for hiking, picnicking, and enjoying nature together.

Things to do recommended for groups

Groups visiting Lakeside can enjoy local flavors at the Round Barn Union Pier Tasting Room, indulge in performances at The Acorn theater, and play a round of golf at Whittaker Woods Golf Course, all while soaking in the area's charming atmosphere.

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

What do I need to keep in mind when booking a vacation in Lakeside

When you're planning a trip—whether you're traveling with a group, with family, bringing your pets, or looking for extended stays—be sure to use the appropriate filters to match your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Lakeside with a group: Think about how many bedrooms you will require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Lakeside with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with amenities that are suitable for their age, like a private swimming pool. Additionally, think about how close you are to attractions that cater to families.
  • Taking your pets with you to Lakeside: For many families, a vacation wouldn’t feel complete without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that your entire family feels comfortable and at home.
  • Planning for a long term stay visiting Lakeside: If you’re searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Additionally, think about including features like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Lakeside

Lakeside, Michigan, offers a picturesque escape perfect for outdoor enthusiasts and romantic getaways. Explore stunning lakefront estates and soak in breathtaking lake views at this idyllic vacation destination. Nearby cities provide a blend of family-friendly activities, luxury relaxation, and budget-friendly options, ensuring a memorable experience for all travelers. Whether you're seeking recreation or a peaceful retreat, Lakeside and its charming surroundings promise an unforgettable adventure.

  • New Buffalo: Located 5 miles from Lakeside, New Buffalo is a charming city known for its stunning outdoor scenery and romantic atmosphere. Visitors flock to this picturesque destination for its beautiful beaches and recreational areas that invite relaxation and adventure. The scenic shoreline along Lake Michigan offers opportunities for swimming, sunbathing, and various water sports. Nature enthusiasts can explore the nearby national state park, which boasts hiking trails and lush landscapes. The city also features local attractions like playgrounds and body treatment venues, making it a perfect spot for families and couples looking to unwind.
  • Union Pier: Just 2 miles from Lakeside, Union Pier is a delightful city that beckons those seeking outdoor adventures and breathtaking scenery. Known for its welcoming atmosphere, this community offers a range of recreational areas, playgrounds, and campgrounds, ideal for both relaxation and exploration. The stunning beach along Lake Michigan provides ample opportunities for sun-soaked days and water activities. Additionally, the nearby national state park enriches the experience with hiking and nature walks, allowing visitors to immerse themselves in the stunning natural beauty of the region.
  • Sawyer: Situated 5 miles from Lakeside, Sawyer is a quaint city that captures the essence of adventure and scenic landscapes. Known for its proximity to national state parks, visitors can enjoy a variety of outdoor activities, including hiking and camping. The area is also home to beautiful lakes and majestic dunes, providing a unique backdrop for exploration. Recreational areas and playgrounds cater to families, ensuring there’s something for everyone. Whether you're looking to hike through picturesque landscapes or relax by the water, Sawyer offers a perfect blend of fun and tranquility.

Best time to go to Lakeside

If you're planning a trip to Lakeside, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.8°F (-2.9°C)Light RainMostly CloudyAverageSlightly Low
February27.9°F (-2.3°C)Light RainMostly CloudyAverageSlightly Low
March37.4°F (3.0°C)Light RainMostly CloudyAverageSlightly 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 HighSlightly High
July72.3°F (22.4°C)Light RainMostly SunnyModerately HighSlightly High
August71.4°F (21.9°C)Light RainMostly SunnyModerately HighSlightly High
September65.8°F (18.8°C)Light RainMostly SunnyAverageAverage
October54.5°F (12.5°C)Light RainMostly SunnyModerately LowAverage
November42.3°F (5.7°C)Light RainMostly SunnyModerately LowAverage
December33.8°F (1.0°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is simple

Are you eager to save on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, utilize our filters to narrow down options by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on eligible reservations. Sign up today and start enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly area to plan new trips, resume your previous work, or manage your travel arrangements. You'll find your saved or booked properties neatly organized into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Head to the historic city of Lakeside

The area's architecture and history are just a few of the reasons to vacation in Lakeside. This city's lake, beaches and forests draw many visitors. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Relaxation reigns supreme in Lakeside

While chilling on the beach is the main attraction of Lakeside vacation rentals, the area also has several wineries. On the outskirts of town is St. Julian Winery, which offers a variety of ciders, red wines, white wines, and spirits. Also nearby is Round Barn, a winery, distillery, and brewery that lets you sample up to six wines or spirits at a time. Other activities near Lakeside include teeing off for a round of golf at the Chikaming Country Club or taking a gamble at Four Winds Casino.

Quiet beaches and quaint shops in Lakeside

There are plenty of activities in Lakeside to keep you happy, whether you’re on a romantic couple’s getaway or a large family vacation. Many people prefer to simply lounge on the area’s private beaches, enjoying the sun or cooling off in the water. The water is also great for fishing, boating, and kayaking if you get tired of taking it easy. Water not your thing? Skip the beaches and head Downtown to experience Lakeside shopping. You’ll be able to hit up antique stores and other small, country shops.

Savor your days in the sun at Lakeside

A typical Lakeside weather forecast in the summer is bright and warm, with average temperatures in July reaching around 80 degrees. Because of this, if swimming and water sports are your game, you’ll want to search for Lakeside vacation rentals in June through August. Late spring and early fall can be just as pleasant without quite as much heat, with average highs in April and October reaching the 60s. Visiting during these times is a great option if you just want to lounge on the beach without getting wet.

Beaches, birding, and parks in Lakeside

With acres of waterfront surrounded by lush green trees, Lakeside is an idyllic paradise for those craving relaxation. Terrain is mostly flat and easily walkable by foot, meaning you can leave the car parked. While most of the Lakeside beaches are private, you can access public beaches at nearby New Buffalo and Warren Dunes State Park. Warren Dunes State Park also features a number of waterfront hikes spread out over an expanse of 1,952 acres. Bird lovers staying in Lakeside can rejoice, as there are 353 different bird species throughout the entire Harbor County area to observe.

Traveling to and around Lakeside

Fly into South Bend Intl. Airport (SBN), the closest airport, located 21 mi (33.8 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Chicago Midway Airport (MDW), which is 55.4 mi (89.2 km) away.

Frequently asked questions

What is the best area to stay in Lakeside when booking a vacation rental?
When planning a vacation in Lakeside, Michigan, a popular area to stay is the charming neighborhood near Lake Michigan. This area offers a serene atmosphere with stunning views of the lake and easy access to beautiful beaches, making it superb for relaxation and outdoor activities. You'll find numerous vacation rentals here, ranging from cozy cottages to more spacious homes, suiting various group sizes.

Staying near the lake allows you to enjoy top attractions like Warren Dunes State Park, which is just a short drive away. This park is known for its towering sand dunes, scenic hiking trails, and lovely picnic spots, making it a fantastic destination for families and nature lovers alike. Additionally, the nearby Lakeside Park offers peaceful walking paths and a superb spot for sunset watching, enhancing the overall experience of your stay.

If you're interested in exploring local culture, the area also boasts proximity to charming boutiques and art galleries in the nearby downtown areas, providing a delightful mix of shopping and dining opportunities.
How much does it cost to rent a vacation home in Lakeside?
Prices for vacation rentals in Lakeside vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Lakeside to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Lakeside vacation house rentals?
You can find great discounts on house rentals in Lakeside on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Lakeside?
For renting a beach house in Lakeside, Michigan, the area along Lake Michigan is particularly appealing. The neighborhood near Warren Dunes State Park features a variety of vacation rentals that offer stunning views of the lake and easy access to sandy beaches. Many of these properties come equipped with amenities such as spacious decks, outdoor grills, and fully equipped kitchens, making them superb for families or groups looking to enjoy a lakeside retreat.

Additionally, the Lakeside community is known for its charming atmosphere, with local shops, cafes, and art galleries that add to the experience. Rentals in this area often include features like private beach access, fire pits for evening gatherings, and beautifully landscaped gardens.

For those seeking outdoor activities, the nearby Warren Dunes State Park not only provides great hiking trails and picnic areas but also opportunities for swimming and sunbathing. Many beach houses in this region are designed for comfort, often featuring amenities like air conditioning, Wi-Fi, and laundry facilities to enhance the convenience of your stay. Find your rental near the beach in Lakeside.
What is the most popular type of vacation rental accomodation in Lakeside?
In Lakeside, vacation houses are the most popular type of rental, with around 42 available in the area. These properties typically offer spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios for enjoying the serene surroundings. Many are situated near the beautiful Lake Michigan coastline, providing easy access to beach activities and local parks. Additionally, there are about 23 cottages that add to the charm of the area. These cozy accommodations often feature rustic decor, small gardens, and sometimes even fire pits for evening gatherings.
Are there any family house rentals in Lakeside?
In Lakeside, Michigan, there are numerous family-friendly vacation rentals available, with about 55 options to choose from. This charming lakeside community is known for its tranquil atmosphere and proximity to stunning Lake Michigan beaches, making it an ideal getaway for families.

Many of these homes feature spacious living areas, fully equipped kitchens, and outdoor decks or patios superb for enjoying summer barbecues. Visitors can expect amenities like private yards for kids to play, cozy fire pits for evening gatherings, and in some cases, even access to bicycles or kayaks for exploring the beautiful shoreline.

The locale is close to attractions such as Warren Dunes State Park, where families can hike, swim, or enjoy the sandy beaches. Additionally, Lakeside's quaint shops and local eateries offer a taste of the area's culture and cuisine. See all family-friendly rentals in Lakeside.
Can I rent a vacation home with a pool or hot tub in Lakeside?
In Lakeside, Michigan, there are several vacation homes available for rent that feature pools and hot tubs, with around 13 options to choose from. This charming area, situated along Lake Michigan, offers a serene atmosphere great for relaxation. Travelers can find rentals in tranquil neighborhoods near the lake, where properties often boast amenities such as private pools, hot tubs, spacious decks, and outdoor dining areas, ideal for enjoying the beautiful surroundings.

Many of these homes come equipped with fully stocked kitchens, allowing families to prepare meals together, as well as cozy living spaces for gathering after a day of exploring. The proximity to local beaches and parks adds to the appeal, providing opportunities for outdoor activities like swimming, hiking, and picnicking. Find your rental in Lakeside with a pool or a hot tub.
Can I find long-stay vacation rentals in Lakeside?
A long-stay vacation rental in Lakeside is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Lakeside?
In Lakeside, Michigan, there are several pet-friendly house rentals available, providing travelers with a range of options to accommodate their furry companions. Many of these rentals are situated close to the stunning shores of Lake Michigan, offering easy access to sandy beaches and beautiful waterfront views. Visitors can expect amenities such as spacious backyards, outdoor seating areas, and fully equipped kitchens, making them superb for family gatherings or group vacations.

The Lakeside area features scenic parks, including Warren Dunes State Park, which is just a short drive away. This popular destination offers hiking trails and expansive beach areas where pets are welcome, allowing for enjoyable outdoor experiences. Additionally, the quaint local shops and restaurants in the Lakeside community enhance the overall experience, ensuring that both travelers and their pets can find plenty to explore and enjoy together. See all pet-friendly rentals in Lakeside.
Are there any remote work vacation rentals in Lakeside?
In Lakeside, Michigan, there are numerous vacation rentals suitable for remote work, with around 50 options available. This charming area, known for its stunning lake views and serene natural landscapes, offers properties equipped with essential amenities for a productive stay. Travelers can expect rentals featuring dedicated office spaces, work desks, and high-speed Wi-Fi, ensuring a comfortable and efficient work environment.

The proximity to Lake Michigan provides opportunities for outdoor activities during breaks, such as hiking along scenic trails or enjoying the beach. Many rentals also include additional amenities like full kitchens and outdoor patios, great for relaxing after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Lakeside vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Lakeside with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Lakeside?
In Lakeside, Michigan, vacation rentals typically offer a range of popular amenities that enhance the stay for travelers. Most properties include a kitchen, allowing guests to prepare meals conveniently during their visit. WiFi is commonly available, ensuring that guests can stay connected. Many rentals also feature patios or decks, providing outdoor spaces for relaxation and enjoying the scenic surroundings. Additionally, a coffee or tea maker is often included, great for those cozy mornings.
When is the best time to visit Lakeside for a vacation rental?
The best time to visit Lakeside, Michigan, for a vacation rental is during the peak summer season from June to August, with July being the most popular month. This vibrant period attracts travelers, drawn to the beautiful beaches along Lake Michigan and the plethora of outdoor activities available. Warm temperatures, typically ranging from the mid-60s to mid-80s Fahrenheit, create a great backdrop for swimming, kayaking, and sunbathing.

During these months, you can expect a lively atmosphere, with many events and fun-filled activities taking place in the area. Enjoy leisurely strolls along the shoreline, or take part in local festivals that celebrate the region's rich culture and community spirit. The long summer days provide ample opportunity for sightseeing and exploring the lush landscapes of the nearby Warren Dunes State Park.

For those looking to save on travel costs, consider planning your trip in November. This quieter month offers a unique charm, with fewer crowds and the opportunity to enjoy the tranquil beauty of Lakeside as the fall colors begin to fade. While the temperatures will be cooler, averaging in the low 30s to mid-50s Fahrenheit, the peaceful atmosphere can be refreshing and is great for cozy indoor activities or scenic drives along the lakeside.

Ultimately, the best time to book your vacation rental in Lakeside hinges on your travel preferences—whether you're seeking the bustling energy of summer or the serene beauty of the off-peak months.
How early should I book a Lakeside vacation rental?
Book your Lakeside vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Lakeside?
In Lakeside, Michigan, visitors can enjoy a charming array of attractions centered around the beautiful Lake Michigan shoreline. The Lakeside neighborhood itself is known for its picturesque beaches, such as the scenic Warren Dunes State Park, which offers hiking trails and stunning views of the lake. The area is also home to quaint shops, local art galleries, and eateries that provide a cozy, small-town atmosphere.

Just a short drive away in nearby Harbert, travelers can explore the vibrant local art scene and enjoy wine tastings at several nearby vineyards. The surrounding countryside features lovely hiking paths and opportunities for outdoor activities, making it ideal for nature enthusiasts.

Additionally, the nearby town of Sawyer offers a blend of recreational activities and local culture, with attractions like the New Buffalo beach and the scenic Galien River County Park, superb for kayaking and birdwatching.
Can I change or cancel my Lakeside home rental booking on Vrbo?
To find Lakeside vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Lakeside vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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