Lakeside vacation rentals

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Welcome to the enchanting shores of Lakeside, Michigan, where stunning Lake Michigan beaches meet picturesque waterfront hikes, inviting you to unwind in nature's embrace. Explore charming neighborhoods filled with cozy cottages and spacious homes that are perfect for families and groups seeking comfort and adventure. With local attractions like Burnison Galleries and the breathtaking Warren Dunes State Park just moments away, you’ll find endless opportunities to create lasting memories. Embrace the home-like experience of our vacation rentals, where space and amenities make every stay a true getaway.

Holiday rentals with weekly discounts - Lakeside

Showing deals for:Oct 9 - Oct 16

Image gallery for Remodeled cottage with hot tub

Living room with gas fireplace
10 out of 10, Exceptional, (34 reviews)
Exceptional
(34 reviews)

Remodeled cottage with hot tub

Sawyer

8% off
Price is $666
$4,663 for 7 nights
All fees included
Remodeled cottage with hot tub

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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.

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, Michigan, United States of America when booking a vacation rental?
Lakeside, Michigan, offers a charming experience for those looking to book a vacation rental, particularly in the Lakeside neighborhood itself. This area is renowned for its scenic beauty and proximity to Lake Michigan, making it a great spot for relaxation and outdoor activities. You'll find a variety of properties available, ranging from cozy cottages to spacious homes, providing options for different group sizes and budgets.

One of the top attractions in Lakeside is the nearby Warren Dunes State Park, where visitors can enjoy hiking, picnicking, and stunning views of the lakeshore. Additionally, the quaint local shops and galleries in the area add a delightful touch to the experience, allowing guests to explore unique finds and local art.
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's shoreline is particularly appealing. The neighborhood near Warren Dunes State Park is a prime spot, offering easy access to sandy beaches and scenic hiking trails. Here, travelers can find charming vacation homes that often feature amenities like spacious decks, outdoor grills, and fire pits, great for enjoying summer evenings by the lake. Many properties also come equipped with modern kitchens and laundry facilities, suiting families or larger groups.

Additionally, the Lakeside area offers proximity to local attractions such as the quaint shops and eateries in downtown Lakeside, providing a delightful mix of relaxation and convenience. Rentals in this vicinity typically boast beautiful lake views and may even include access to private beach areas, enhancing the overall beach experience. Furthermore, the nearby vineyards and wineries in the surrounding region offer excellent opportunities for wine tasting, making this area not just a beach destination, but also a delightful retreat for those looking to explore local flavors and outdoor activities.
What is the most popular type of vacation rental accomodation in Lakeside?
In Lakeside, vacation houses are the most popular type of rental accommodation, with about 41 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, and amenities such as fully equipped kitchens and outdoor patios, great for enjoying the scenic surroundings. Additionally, there are around 21 charming cottages that provide a cozy, intimate atmosphere, ideal for couples or small families looking for a peaceful retreat near the shores of Lake Michigan.
Are there any family house rentals in Lakeside?
In Lakeside, Michigan, there is a substantial selection of family-friendly house rentals, with around 51 options available. This charming area is known for its beautiful lakes and proximity to various outdoor activities, making it an ideal getaway for families. Many homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for barbecues or enjoying the natural surroundings.

Visitors can also find properties with amenities such as private decks, fire pits for evening gatherings, and easy access to nearby beaches, where children can play and families can relax by the water. The locale is close to attractions like Warren Dunes State Park, which offers hiking trails and sand dunes, adding to the family-friendly experience.
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 or hot tubs, with around 12 options to choose from. This charming area is known for its beautiful beaches along Lake Michigan and a relaxing atmosphere, making it an ideal destination for vacationers seeking leisure and outdoor activities.

Travelers can expect various amenities in these rentals, such as private pools, hot tubs for unwinding after a day at the beach, spacious outdoor areas, and fully equipped kitchens for family meals. Many properties also offer access to nearby hiking trails and local attractions, ensuring a well-rounded vacation experience.
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 numerous pet-friendly house rentals available, with around 28 options to choose from. This charming community along the shores of Lake Michigan offers a variety of accommodations that cater to both travelers and their furry friends. Many vacation rentals in the area come equipped with amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, making them ideal for families or groups looking for a relaxing getaway.

The nearby Warren Dunes State Park is a highlight for pet owners, featuring trails and sandy beaches where dogs are welcome, allowing for enjoyable walks and playtime by the lake. Additionally, the local area has pet-friendly cafes and shops, ideal for those traveling with pets.
Are there any remote work vacation rentals in Lakeside?
In Lakeside, Michigan, there are numerous vacation rentals suitable for remote work, with around 47 options available. Many of these properties are designed to cater to the needs of travelers looking to blend work and leisure. Expect to find amenities such as dedicated workspaces, including desks and ergonomic chairs, along with reliable high-speed internet and Wi-Fi, ensuring a productive environment.

The area itself is known for its serene natural beauty, with nearby attractions like Lake Michigan's stunning beaches and the scenic Warren Dunes State Park, great for outdoor activities during breaks. Rentals in this region often come with inviting features like cozy living areas, fully equipped kitchens, and outdoor spaces to enjoy the fresh air. 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, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many rentals feature decks or patios, providing outdoor spaces to relax and enjoy the serene surroundings. Onsite parking is commonly available, making it convenient for travelers with vehicles. Additionally, rentals often come with coffee and tea makers for those cozy mornings, and fireplaces that create a warm and inviting atmosphere, superb for chilly evenings.
When is the best time to visit Lakeside for a vacation rental?
The best time to visit Lakeside for a vacation rental is during the peak summer season, which runs from June to August. This vibrant period attracts families and outdoor enthusiasts eager to enjoy the stunning beaches along Lake Michigan, partake in water sports, and explore the picturesque trails nearby. July is particularly popular, as visitors flock to the area for its warm weather and the lively option created by seasonal events and community activities.

During the summer months, you can expect pleasant temperatures ranging from the mid-60s to mid-80s Fahrenheit, making it ideal for outdoor adventures such as hiking, biking, and beach outings. The natural beauty of Lakeside, with its lush landscapes and scenic views, enhances the experience, superb for those seeking relaxation or fun-filled days under the sun.

For travelers looking for a more budget-friendly option, November presents a quieter time to experience Lakeside's charm. While the summer crowds have dispersed, visitors can still enjoy the serene beauty of fall, with the opportunity to explore the area's trails and appreciate the stunning autumn foliage.

Ultimately, your choice depends on whether you prefer the lively summer atmosphere full of activities and community spirit or the peacefulness of late fall, superb for a more reflective getaway.
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, Michigan, United States of America?
In Lakeside, Michigan, visitors can enjoy a variety of attractions that highlight the area's natural beauty and charm. The Lakeside community is known for its picturesque views of Lake Michigan, making it a great spot for beachgoers and those who enjoy water activities. The nearby Warren Dunes State Park features rolling sand dunes, hiking trails, and scenic beaches, ideal for picnicking and outdoor sports.

The neighborhood also boasts quaint shops and local eateries that provide a cozy, small-town atmosphere. For those interested in local culture, the area often hosts seasonal festivals and art fairs, showcasing the work of local artists and craftspeople. Additionally, the proximity to vineyards and wineries along the Lake Michigan Shore Wine Trail offers wine enthusiasts a chance to explore tastings and tours in a beautiful setting.
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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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