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Vacation rentals in Lakeside

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Lakeside vacation rentals

Self check-in
Gym
BBQ grill
Laptop-friendly workspace
Wifi

House rentals in Lakeside

Guest favorite
A two-story, light blue house is featured with a welcoming front porch and wooden deck. The deck includes a small seating area, visible alongside well-maintained greenery. Nearby, an adjacent building with a white exterior adds to the neighborhood charm, complemented by a bright sky in the background.
Home in Michigan City
4.9 out of 5 average rating, 138 reviews

Airy and bright, Cottage Blue Welcomes You!

Guest favorite
A spacious living area is presented with a comfortable gray sofa adorned with decorative pillows. Two accent chairs in a blue pattern complement a dark coffee table, while a computer desk is positioned nearby. Soft lighting is provided by recessed lights, and windows are dressed in sheer white curtains.
Home in Berrien Springs
4.95 out of 5 average rating, 124 reviews

Great Living Too

Guest favorite
The private backyard features a covered seating area with comfortable seating arranged around a stone fire pit. A gas grill is situated nearby, and green lawn space surrounds the patio, offering ample room for outdoor activities. The fenced area provides privacy.
Home in South Bend
4.9 out of 5 average rating, 115 reviews

Walk to ND/Eddy Street, ProCleaned/Comfy/Updated

Guest favorite
The kitchen showcases a stainless steel stove and microwave, complemented by open shelving. A dining area with six metal chairs is positioned near the entrance to the living room, which features a sofa and a wall-mounted television.
Home in New Buffalo
4.82 out of 5 average rating, 400 reviews

Sq Toe's Last Resort:Pet-Friendly*Fenced* GameRoom

Guest favorite
An open-concept living space features a modern kitchen with white cabinets and a dark countertop. A dining table with six chairs is positioned in front, while the living area includes multiple seating options, offering a relaxed environment with a warm wooden floor throughout.
Home in Michigan City
4.89 out of 5 average rating, 113 reviews

Roomy and Private Getaway for Families & Friends

Guest favorite
Two patterned armchairs with vibrant yellow and blue throw pillows are positioned near a window. A small round table with a decorative plant sits between the chairs. A plush area rug with a geometric design complements the seating arrangement, contributing to a cozy atmosphere.
Home in South Bend
4.86 out of 5 average rating, 167 reviews

Irish Retreat

Guest favorite
A dramatic scene is captured featuring a lighthouse on a pier, surrounded by dark storm clouds. Lightning strikes illuminate the sky, reflecting over the water's surface. The structure stands prominently, with its red top contrasting against the ominous backdrop.
Home in Michigan City
4.9 out of 5 average rating, 373 reviews

Best Deal In Michigan City 1.3 miles to Beach

Superhost
A spacious living area is highlighted by a large sectional sofa and a modern ceiling fan. Natural light enters through large windows, illuminating a decorative fireplace. A dartboard is mounted on the wall, and a small table is positioned nearby, enhancing the inviting space.
Home in South Bend
4.85 out of 5 average rating, 158 reviews

3BR w/sauna, tanning bed, hot tub 3.9 miles fromND

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Lakeside fishing vacation rentals

Superhost
A seating area is arranged on a wooden deck, featuring a sectional sofa and a coffee table. The sunset casts warm colors over the lake in the background, while silhouettes of trees frame the view. A boat is visible at the pier, enhancing the lakeside atmosphere.
Cottage in Decatur
4.89 out of 5 average rating, 123 reviews

Charming Cottage on the Lake

Superhost
A large, well-lit bedroom features double French doors leading to a deck overlooking the green landscape. Natural light streams in through the upper window, enhancing the spacious feel. Light-colored carpet is visible, along with a glimpse of a bed adorned with a floral pattern.
Guesthouse in Berrien Springs
4.92 out of 5 average rating, 246 reviews

Make Lasting Memories at Beautiful Lake Chapin

Top guest favorite
A secluded log home is depicted, surrounded by lush green woods. A spacious deck extends across the front, with seating and a hammock visible. A fire pit area features circular stones and bright red chairs, inviting relaxation outdoors.
Cabin in Hartford
4.97 out of 5 average rating, 317 reviews

Secluded Log Home - Private Lake!

Guest favorite
A pontoon boat is docked in calm waters, surrounded by wooden docks. The clear water exhibits a gentle gradient, showcasing sandy bottom beneath. The horizon is visible under a clear blue sky, emphasizing a serene waterfront setting.
Chalet in La Porte
4.93 out of 5 average rating, 421 reviews

Pet friendly, lakefront home w/kayaks & pontoon!

Guest favorite
A spacious patio is featured with a shaded seating area, accommodating several chairs around a central table. Surrounding flowers bring color to the outdoor space, complemented by a barbecue grill. The lake is visible in the background, enhancing the scenic view.
Apartment in La Porte
4.93 out of 5 average rating, 490 reviews

Second Floor Apartment sitting on Pine Lake

Guest favorite
The two-story lakefront home is visible with a yellow exterior and red roof. A spacious deck surrounds the house, offering seating areas. The tranquil lake extends along the backyard, and two dogs can be seen walking on the grassy area in front.
Home in Vandalia
4.86 out of 5 average rating, 197 reviews

Quiet Lakefront Vacation House near Notre Dame

Top guest favorite
A charming cottage is positioned near the water, with a gentle sunset illuminating the scene. The exterior features light-colored siding and large windows. Adjacent greenery provides a serene backdrop, while the pathway leads toward the lake, enhancing accessibility and scenic views.
Cottage in Coloma
4.95 out of 5 average rating, 182 reviews

Lake View Cottage

Guest favorite
A spacious cottage is surrounded by tall trees, offering shade and a relaxing environment. A large deck extends from the back, while a fire pit area with Adirondack chairs sits on the grassy lawn, inviting outdoor gatherings.
Cottage in Dowagiac
4.96 out of 5 average rating, 116 reviews

The Wildwood Cottage, private lake access

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Lakefront house rentals in Lakeside

Guest favorite
A serene view of Barron Lake features calm waters reflecting the clear blue sky. An American flag stands prominently on a dock, with grassy areas leading to the water's edge. Soft clouds are visible in the sky, enhancing the tranquil ambiance.
Home in Niles
4.94 out of 5 average rating, 50 reviews

Relaxing Lakefront House-Perfect Family Vacation

Guest favorite
A lakefront view reveals a charming house with a porch and multiple seating areas on the lawn. A private dock extends into the water, accommodating a pontoon. Green trees provide shade, while an American flag gently waves in the breeze.
Home in Valparaiso
4.95 out of 5 average rating, 129 reviews

Lakefront House, Pontoon, Deck, Fire Pit & More!

Guest favorite
A private pool area is framed by a white fence, featuring a clear blue pool surrounded by lounge chairs. Lush greenery and a large tree provide shade, while the serene view of Lake Chapin and distant trees is visible in the background.
Home in Berrien Springs
4.91 out of 5 average rating, 121 reviews

Lake House Retreat with a Pool

Top guest favorite
A spacious two-story home is depicted, featuring a wooden deck with seating and a staircase leading to it. The exterior showcases a mix of siding and stone. The backyard, with trimmed grass, includes outdoor chairs positioned for relaxation.
Home in Cassopolis
4.94 out of 5 average rating, 109 reviews

Kelsey Lake Lake house 22 miles to Notre Dame

Top guest favorite
The beach at The Windover features soft, sandy shores with gentle waves lapping at the water's edge. The cottage, showcasing a modern design, stands nearby with large windows and a welcoming porch. A seating area adorned with a candle and flowers offers a perfect spot to relax.
Home in Benton Harbor
4.99 out of 5 average rating, 151 reviews

Private Beach/Lake Michigan/Panoramic View/Hot Tub

Top guest favorite
An aerial view shows a bright blue house surrounded by green grass and trees. A spacious wooden deck is furnished with seating and an umbrella. Two kayaks are stored along the deck's edge, highlighting outdoor leisure opportunities.
Home in Coloma
5 out of 5 average rating, 18 reviews

Waterfront 4BR/2.5BA W/2 Large Decks | Haven K

Guest favorite
The front of a single-story home is framed by a large tree, with green ferns and grass in the yard. A spacious porch area is visible, inviting relaxation and enjoyment of the natural surroundings.
Home in Sawyer
4.92 out of 5 average rating, 132 reviews

Dunes Beach Retreat House

Guest favorite
Kayaks in vibrant blue and red are positioned on the lush green lawn by the water's edge, alongside a parked pontoon boat. A large tree provides shade, while the calm lake reflects clear blue skies and surrounding greenery.
Home in Decatur
4.96 out of 5 average rating, 56 reviews

Luxury on the Lake: Southwest Michigan Retreat!

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Your guide to Lakeside

Introduction

Chicago residents have been escaping to the southeast coast of Lake Michigan for a century, and hidden among the tree-lined beaches of Lakeside are thousands of rustic cottages and inns. This is a retreat designed for relaxation: You can hike in the woods, swim, bike, go wine tasting, or just do nothing — many people are here specifically to soak up the sun and spend long afternoons reading amid the trees. Many shops, bars, and antique stores along Red Arrow Highway cater to urban tastes, and the mood is serene and friendly. (Lakeside is not an isolated getaway, however, and if you need to buy supplies, Michigan City, just over the Indiana border, is only 20 minutes away.)

The best time to stay in a vacation rental in Lakeside

If you prefer gentle climates, May through September are definitely the best months to visit the southern Lake Michigan coast. The lake tempers the heat during the summer, but temperatures in the 80s Fahrenheit are still common. As July segues into August the humidity goes up — you’ll want to make frequent trips to the lake to cool down. (Essential protections: sunglasses, sunblock, and bug spray.)

Autumn, which begins in mid-September, is a magnificent time to stay in one of the area’s cottage rentals, with crisp air and brilliantly colored foliage. Winters stretch from early December to the beginning of March. During those months, temperatures below the 40s Fahrenheit are the norm, and the lakeshore effect brings freezing winds and snows to much of southern Michigan and northern Indiana.

Top things to do in Lakeside

Warren Dunes State Park

Warren Dunes is kind of the Riviera of the southern coast, with miles of fine-sand beach that fills up with castle-builders and sun-seeking teenagers. If you hear excited screaming, look up to see kids who have climbed to the top of a 250-foot sand dune flying or rolling down.

Red Arrow Highway

This north-south road connects the towns of the southeastern Michigan coast, and the stretch from New Buffalo to Bridgeman is lined with galleries, craft stores, and antique shops selling both knickknacks and high-end furniture. You can also find welcoming cafes, roadhouses, and a beloved Turkish restaurant.

Three Oaks

The town of Three Oaks, just a few miles inland from Lakeside, is the center of the region’s biking culture. You can rent bikes from little cruisers to heavy-duty mountain bikes, and there’s a bike museum. Three Oaks has created 20 bike routes that range from short and flat to September’s Apple Cider Century bike tour of wine and orchard country.

Destinations to explore

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