Lakeside holiday lettings

We found 828 holiday rentals — enter your dates for availability
Select from 45 homes, 22 cottages and other holiday rentals in Lakeside to find one that's perfect for your trip. Holiday rentals provide the amenities that you need and want for you and your friends, family or even pets, such as a hot tub and a washer and dryer. You're sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Lakeside

Showing deals for:29 Jan - 5 Feb

Image gallery for LUXURY Lakefront Property on Private Beach with Stunning Lake Views and Sunsets

Screened in porch on back deck
10 out of 10, Exceptional, (130 reviews)
Exceptional
(130 reviews)

LUXURY Lakefront Property on Private Beach with Stunning Lake Views and Sunsets

Union Pier

8% off
Price is £8,646
for 7 nights, 1 home
£1,235 per night
includes taxes & fees
LUXURY Lakefront Property on Private Beach with Stunning Lake Views and Sunsets

Find spaces that suit your style

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Why visit Lakeside

  • Stunning Beaches: Lakeside boasts beautiful sandy beaches along Lake Michigan, ideal for relaxation and family fun.
  • Scenic Nature Reserves: Explore picturesque hiking trails and nature reserves that showcase the area's stunning natural beauty.
  • Charming Waterfront Community: Enjoy romantic strolls and vibrant community life in this quaint lakeside town.
  • Local Art and Dining: Discover delightful local art galleries and savour delicious dining options that reflect the region's charm.
  • Serene Atmosphere: Experience a peaceful retreat in a friendly environment, perfect for creating lasting memories.

Popular types of accommodation in Lakeside

Discover the charm of Lakeside, Michigan, a delightful destination for your next getaway. Nestled along the picturesque shores of Lake Michigan, this quaint town offers stunning natural beauty, sandy beaches, and scenic parks. Visitors can enjoy leisurely strolls, local art galleries, and delightful dining options. With a selection of houses, cottages, and apartments, Lakeside is perfect for families and groups seeking a relaxing retreat in a serene environment.

  • Houses: The top choice for visitors seeking a homely experience, offering spacious living and all necessary amenities.
  • Cottages: Charming retreats that provide a quaint atmosphere, perfect for those looking for a cosy getaway.
  • Apartments: Conveniently located living spaces, ideal for couples or solo travellers wanting easy access to local attractions.
  • Condos: Modern accommodations combining comfort with community amenities for a delightful stay.
  • Cabins: Rustic hideaways nestled in nature, perfect for an authentic outdoor experience.**

Top attractions near Lakeside

Lakeside, Michigan, offers a charming escape for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can enjoy beautiful beaches and serene lakes, perfect for relaxing and picnicking. The local nature reserves provide excellent opportunities for scenic hikes along the waterfront, allowing exploration of the area's stunning natural beauty. With its friendly atmosphere and picturesque surroundings, Lakeside is an ideal destination for those looking to connect with nature and create lasting memories.

  • New Buffalo Public Beach: A picturesque beach offering a relaxing atmosphere with soft sand and gentle waves, perfect for sunbathing and picnicking.
  • Warren Dunes State Park: An outdoor enthusiast's paradise featuring towering sand dunes, hiking trails, and stunning views of Lake Michigan, ideal for adventure seekers.
  • Saugany Lake: A serene lake surrounded by lush scenery, providing a romantic setting for kayaking, fishing, and enjoying tranquil sunsets.

Things to do recommended for couples

For a romantic getaway in Lakeside, explore the serene beaches at sunset or indulge in a wine tasting at a local vineyard. Take a leisurely stroll along the charming lakeside paths and enjoy a cosy dinner at a quaint restaurant, perfect for couples seeking intimacy.

Things to do recommended for families

Families visiting Lakeside, Michigan can enjoy a delightful day at Warren Dunes State Park, where children can explore sandy beaches and hike scenic trails. Additionally, take a trip to the nearby Michigan Maritime Museum for interactive exhibits that engage young minds with maritime history.

Things to do recommended for groups

Groups visiting Lakeside can enjoy thrilling motor racing at Red Bud Track-N-Trail, located 26km away, or experience the excitement at South Bend Motor Speedway, situated 32km from Lakeside. Both venues offer an adventurous atmosphere perfect for group travellers.

*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

If you're travelling with a group, family, or pets, or if you're seeking longer stays, it's important to refine your search according to your specific needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Lakeside with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group get-togethers. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Lakeside with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Lakeside: For many, a family holiday isn't truly complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Lakeside: If you’re in search of holiday rentals offering 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. Don’t forget to include amenities such as a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Lakeside

Lakeside, Michigan, offers a charming escape with its stunning beaches along the coast of Lake Michigan. Visitors can revel in the picturesque waterfront community, perfect for romantic strolls or family-friendly activities. Enjoy the serene vibes of the lakeside parks, indulge in outdoor recreation, and immerse yourself in the area's rich history. Whether you seek relaxation or adventure, Lakeside’s inviting atmosphere and natural beauty provide a delightful backdrop for an unforgettable vacation.

  • New Buffalo: Located 8km from Lakeside, New Buffalo is a charming city that beckons visitors with its stunning outdoor scenery and romantic atmosphere. The city is known for its picturesque recreational areas and playgrounds, making it ideal for families and couples alike. When in New Buffalo, be sure to visit the local lake and beach, where you can bask in the sun or enjoy water activities. The nearby national state park offers beautiful trails and lush landscapes, perfect for hiking and exploring. With its beautiful surroundings and relaxed vibe, New Buffalo promises a delightful escape.
  • Union Pier: Just 3km away from Lakeside, Union Pier is a quaint city renowned for its outdoor charm and breathtaking scenery. This idyllic destination is perfect for a romantic getaway or a family outing, offering a variety of recreational areas, playgrounds, and campgrounds. The proximity to the lake and beach allows for leisurely days by the water, while the national state park nearby provides ample opportunities for nature walks and wildlife viewing. Union Pier's serene environment and beautiful landscapes make it a must-visit spot for those seeking relaxation and adventure.
  • Sawyer: Situated 8km from Lakeside, Sawyer is an enchanting city celebrated for its scenic beauty and adventurous spirit. This area is perfect for those who enjoy the great outdoors, with numerous recreational areas, playgrounds, and campgrounds to explore. The nearby national state park features stunning dunes and a picturesque lake, making it ideal for hiking, picnicking, and discovering the natural landscape. Sawyer's blend of adventure and tranquility invites visitors to immerse themselves in its breathtaking surroundings and create lasting memories.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 hoping to cut costs on your next adventure? Being flexible with your travel dates can be beneficial, as prices often vary. Additionally, opting for a longer stay typically allows for substantial savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, revisit your existing arrangements, or keep your bookings well-organised. Your saved or booked properties are neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Head to the historical city of Lakeside

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

Activities and attractions in and around Lakeside

Do you want to discover things to do during your stay? Venture out of your cosy holiday rental and experience everything that Lakeside has to offer. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • St. Julian Winery - Union Pier Tasting Room (1.5 mi / 2.3 km)
  • Round Barn Union Pier Tasting Room (1.5 mi / 2.4 km)
  • Whittaker Woods Golf Course (7.2 mi / 11.6 km)
  • Round Barn Baroda Tasting Room & Estate (11.8 mi / 19 km)
  • Round Barn Winery (11.9 mi / 19.1 km)
  • Tabor Hill Winery (12 mi / 19.2 km)

Exploring the natural features in Lakeside

Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Lakeside. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Gordon Beach (1.7 mi / 2.7 km)
  • Union Pier Beach (1.9 mi / 3.1 km)
  • Cherry Beach (2.8 mi / 4.6 km)
  • Townline Beach (2.9 mi / 4.7 km)
  • Galien River County Park (4 mi / 6.5 km)
  • Warren Dunes State Park Beach (5.1 mi / 8.2 km)

Travelling to and around Lakeside

Fly into South Bend, IN (SBN-South Bend Intl.), the closest airport, located 21 mi (33.8 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into 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 holiday rental?
When considering a holiday rental in Lakeside, Michigan, the area around the charming Lakeside neighbourhood is a fantastic choice. This picturesque community is known for its stunning lake views and a relaxed, welcoming atmosphere. You'll find a variety of properties available, ranging from quaint cottages to modern homes, making it easy to find something that suits your needs.

In Lakeside, visitors can enjoy the beautiful beaches along Lake Michigan, superb for sunbathing or taking a refreshing dip. The nearby Warren Dunes State Park is a must-visit, offering miles of hiking trails, towering sand dunes, and opportunities for picnicking amidst nature. Additionally, the local shops and eateries provide a delightful experience, showcasing the community's vibrant culture.
How much does it cost to rent a holiday home in Lakeside?
Prices for holiday 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 holiday 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 around Warren Dunes State Park is highly recommended. This picturesque stretch of coastline along Lake Michigan offers a variety of charming rental properties with stunning views and direct access to sandy beaches. Many of these houses come equipped with amenities such as spacious decks for outdoor dining, fire pits for evening gatherings, and fully stocked kitchens ideal for self-catering.

Another top area is the Lakeside community itself, where you'll find quaint cottages and modern homes located among lush greenery. These properties often feature private outdoor spaces, superb for enjoying the serene surroundings. Many also include amenities like air conditioning, laundry facilities, and Wi-Fi, ensuring a comfortable stay for families or groups.

Additionally, the nearby town of New Buffalo provides further options, with its vibrant waterfront and local shops. Rentals here might offer proximity to both the beach and recreational activities, such as boating or biking, along with amenities like hot tubs or access to community pools.
What is the most popular type of holiday rental accomodation in Lakeside?
In Lakeside, holiday houses are the most popular type of holiday rental, with around 123 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, and amenities such as fully equipped kitchens and outdoor patios or decks, making them ideal for families or larger groups. Additionally, there are approximately 63 cottages that provide a charming and cosy atmosphere, great for those seeking a more rustic experience. Cottages typically include essential comforts and often are located near the scenic lakeshore, allowing guests to enjoy the natural beauty of Lakeside.
Are there any family house rentals in Lakeside?
In Lakeside, Michigan, there are numerous family-friendly house rentals available, with around 51 options to choose from. This charming locale offers a delightful mix of nature and community, great for families looking to enjoy a relaxing getaway. Many homes feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces where children can play and explore.

Visitors can enjoy the nearby beaches along Lake Michigan, which are great for swimming and picnicking, as well as local parks that provide hiking trails and playgrounds. The area is also known for its charming shops and art galleries, offering a taste of local culture.
Can I rent a holiday home with a pool or hot tub in Lakeside?
In Lakeside, Michigan, there are several holiday homes available for rent that come equipped with pools or hot tubs, with around 12 options to choose from. This charming area, located near Lake Michigan, offers a delightful mix of relaxation and recreational activities. Many of these properties often feature private pools, inviting hot tubs, and spacious outdoor areas, great for enjoying the summer sun or unwinding after a day of exploring.

Travellers can also expect to find modern amenities such as fully equipped kitchens, outdoor dining spaces, and comfortable living areas, making these rentals ideal for families or groups. The proximity to the lake means that guests can enjoy water activities, while local attractions like vineyards and nature trails add to the overall appeal of the region.
Can I find long-stay holiday rentals in Lakeside?
A long-stay holiday rental in Lakeside is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Lakeside?
In Lakeside, Michigan, there are several pet-friendly house rentals available, with a total of around 28 options to choose from. This charming area is known for its beautiful natural surroundings and proximity to Lake Michigan, making it an appealing destination for pet owners. Many of the holiday homes come equipped with modern amenities such as fully equipped kitchens, spacious living areas, and private outdoor spaces where pets can enjoy the fresh air.

Lakeside is in close proximity to numerous parks and recreational areas, allowing for enjoyable walks and outdoor activities with your pet. The nearby Warren Dunes State Park is a highlight, featuring sandy beaches, hiking trails, and picnic areas, making it superb for a day out with your furry friend.
Are there any remote work holiday rentals in Lakeside?
In Lakeside, Michigan, there are numerous holiday rentals suitable for remote work, with around 141 options available. This charming area near Lake Michigan offers a tranquil environment, ideal for those looking to blend work and leisure. Many properties come equipped with essential amenities such as free Wi-Fi, dedicated workspaces, and comfortable desks, ensuring a productive atmosphere.

Travellers can expect a range of accommodations, from cosy cottages to spacious homes, often featuring outdoor areas for relaxation after a day's work. The scenic surroundings include beautiful beaches, parks, and access to local attractions, providing opportunities for outdoor activities and exploration during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Lakeside holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Lakeside with parking available—perfect for families or travellers 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, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals and enjoy a home-cooked experience. Many rentals feature decks or patios, providing a lovely outdoor space to relax and take in the serene surroundings. Onsite parking is a common convenience, making it easy for guests to access their accommodations. Additionally, a coffee or tea maker is typically included for those who appreciate a warm beverage in the morning. Many properties also offer fireplaces, creating a cosy atmosphere for guests to unwind after a day of exploring the beautiful area.
When is the best time to visit Lakeside for a holiday rental?
The best time to visit Lakeside for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts families and outdoor enthusiasts eager to enjoy the sun-soaked beaches along Lake Michigan and partake in various water activities, such as swimming, kayaking, and paddleboarding.

During the summer months, Lakeside basks in warm temperatures, often reaching the low 30s Celsius, creating a delightful environment for outdoor adventures and leisurely strolls along the picturesque shoreline. The charming local shops and restaurants come to life, offering a range of delightful experiences that cater to diverse tastes.

For those seeking a more budget-friendly option, consider visiting in November. This quieter month allows for a peaceful retreat, where you can enjoy the serene beauty of Lakeside as the autumn leaves create a stunning backdrop. It's a superb time for leisurely walks and cosy evenings, providing a different yet equally enjoyable experience.
How early should I book a Lakeside holiday rental?
Book your Lakeside holiday 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 holiday 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 variety of attractions that highlight the area's natural beauty and charm. The pristine beaches along Lake Michigan are a major draw, offering opportunities for swimming, sunbathing, and beachside picnics. The nearby Warren Dunes State Park features towering sand dunes and scenic trails, great for hiking and nature walks.

The quaint town centre is home to local shops, boutiques, and eateries that provide a taste of the community's vibrant culture. For those interested in wine, the surrounding vineyards and wineries offer tastings and tours, showcasing the region's burgeoning wine scene.

Additionally, the Lakeside area is known for its art galleries and seasonal events, which often feature local artists and craftspeople, making it a fantastic place to explore and experience the arts.
Can I change or cancel my Lakeside home rental booking on Vrbo?
To find Lakeside holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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