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Vacation rentals in Lakeside

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Vacation rentals for every style

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Popular amenities for Lakeside vacation rentals

Gym
BBQ grill
Laptop-friendly workspace
Wifi
Air conditioning

Lakeside house rentals

Top guest favorite
An outdoor relaxation area features a hot tub and a smokeless firepit, surrounded by comfortable seating. String lights hang above, illuminating the space. A small set of steps leads into the hot tub, with a towel draped casually over the railing. The grassy area provides a serene backdrop.
Home in Three Oaks
4.99 out of 5 average rating, 106 reviews

Pet friendly stylish retreat with sauna, hot tub

Guest favorite
A spacious screened porch features a cozy seating area with a blue sofa adorned with colorful cushions. A coffee table sits in the center, surrounded by views of the lush greenery outside through large screens and wooden accents, creating a serene space to relax.
Home in Lakeside
4.98 out of 5 average rating, 81 reviews

The Honey Bee Lakeside

Guest favorite
A newly renovated kitchen features modern cabinetry in muted tones, with light-colored countertops and a gas range. Stainless steel appliances include a refrigerator and a coffee maker. Natural light enters through a window above the kitchen sink, creating a bright and functional space.
Home in Three Oaks
4.96 out of 5 average rating, 139 reviews

The Heartwood House<3 : DT Three Oaks w/Game Room

Guest favorite
An open great room features a large dining table at the center, surrounded by colorful chairs. A striking stone wall with a fireplace adds character, while large windows provide ample natural light. Cozy seating areas can be seen in the background, contributing to the inviting layout.
Home in Sawyer
4.94 out of 5 average rating, 160 reviews

Beautifully eclectic Sawyer cottage

Guest favorite
The vintage cottage is framed by lush greenery, featuring a welcoming front porch with a bright yellow door. A landscaped pathway leads to the entrance, with decorative stonework and potted plants accentuating the outdoor space.
Home in New Buffalo
4.85 out of 5 average rating, 222 reviews

Cozy Vintage Cottage Near the Lake

Top guest favorite
A comfortable living space features a vintage green cabinet and a wooden dining table surrounded by black chairs. Natural light floods the room through large windows, enhancing the cozy atmosphere created by soft furnishings and decorative plants.
Home in Three Oaks
4.97 out of 5 average rating, 191 reviews

Casa Gitana - Boutique Style Stay in Three Oaks

Superhost
An open living space showcases a blend of modern and rustic design elements. A spacious kitchen features stainless steel appliances, with bar stools positioned at the counter. Natural light filters in through large windows, illuminating the polished hardwood floors.
Home in Union Pier
4.91 out of 5 average rating, 225 reviews

CASA TICA Serenity Amongst Nature Dog Friendly

Guest favorite
The living area showcases a modern design with a black sectional sofa and comfortable armchairs. A wooden coffee table is positioned at the center, and wooden beams complement the ceiling. A staircase leads to an upper level, while a large circular mirror enhances the space.
Home in Three Oaks
4.96 out of 5 average rating, 198 reviews

The Walnut House, Michigan Woods Retreat

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Lakeside cottage rentals

Top guest favorite
The exterior of the cottage is surrounded by trees, with a designated seating area featuring two blue Adirondack chairs and a wooden table. A firepit sits in the gravel yard, offering a natural gathering space among green foliage.
Cottage in Union Pier
4.97 out of 5 average rating, 141 reviews

Beach Bird Cottage- 5min walk to the lake! 3BR/1BA

Top guest favorite
A cozy cottage is nestled among lush green ferns and trees, with vibrant flowering shrubs nearby. The structure features a gabled roof and large windows, providing a glimpse of the welcoming interior. A picket fence frames the scene, adding charm to the natural surroundings.
Cottage in Michiana Shores
4.99 out of 5 average rating, 139 reviews

The Pines Cottage on Birchwood

Guest favorite
The exterior of the barn showcases a vibrant red facade adorned with greenery. Large overhanging vines and trees frame the entrance, creating a welcoming atmosphere. A paved area leads to the barn, with side windows visible on the left. This setting hints at a rustic charm.
Cottage in Sawyer
4.88 out of 5 average rating, 194 reviews

Northwind Llama retreat 'Loft Cottage'

Guest favorite
A modern white home is pictured, featuring a welcoming front porch supported by wooden posts. Multicolored stones create a path leading to the doorway, surrounded by neatly landscaped greenery on a newly mulched yard. Natural light reflects off large windows, inviting a peaceful ambiance.
Cottage in New Buffalo
4.96 out of 5 average rating, 108 reviews

Casa Playa New House in Union Pier w/ Private Spa

Guest favorite
A serene sunset is captured over a calm lake, with hues of orange and pink blending in the sky. Silhouetted trees frame the view, while a hanging chair is visible in the foreground, offering a cozy perspective of the tranquil scene.
Cottage in Benton Harbor
4.95 out of 5 average rating, 100 reviews

Lake Bluff cottage, Unforgettable view and sunsets

Top guest favorite
A spacious wooden deck is adorned with soft string lights overhead, creating a cozy ambiance. Two comfortable chairs and a small table are positioned for relaxation. A potted plant with bright yellow flowers adds a touch of color to the inviting outdoor space.
Cottage in New Buffalo
4.98 out of 5 average rating, 200 reviews

New Buffalo retreat - Perfect year-round getaway!

Guest favorite
A bright living room features high ceilings with a chandelier above a central wooden coffee table. Comfortable dark gray sofas are positioned around the table, complemented by decorative cushions. Large windows allow natural light to fill the space, and a stone fireplace adds a cozy focal point.
Cottage in Union Pier
4.96 out of 5 average rating, 212 reviews

Designer Cottage Relax Beach Pool & Spa—Windjammer

Guest favorite
The exterior of the cottage is showcased, featuring a welcoming dark grey facade. The front yard contains well-maintained greenery and small trees. Two large picture windows allow natural light into the interior, while a small patio leads to the entrance.
Cottage in Union Pier
4.9 out of 5 average rating, 155 reviews

Camp Wanderlust-Cozy lodge-20 minute walk to beach

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Lakeside fishing vacation rentals

Guest favorite
An outdoor area features a private heated pool surrounded by a black safety fence and lush greenery. Comfortable lounge chairs are scattered around the pool deck, with a large blue umbrella providing shade. A picnic table is visible, creating a welcoming space for relaxation.
Home in Michiana Shores
4.93 out of 5 average rating, 103 reviews

Splash (Pool! Hot Tub!) at Aqua House by the Lake

Guest favorite
A charming green cottage is nestled among trees, surrounded by well-kept landscaping and flower pots. A red umbrella shades a picnic table nearby, creating a welcoming outdoor space. The gravel path leads to the cottage entrance, framed by large windows for natural light.
Guesthouse in Benton Harbor
4.94 out of 5 average rating, 181 reviews

Cozy Green Cottage with Private Beach

Guest favorite
An outdoor deck is furnished with a large dining table surrounded by six floral-patterned chairs, providing ample seating for gatherings. A large umbrella offers shade over the table, while a comfortable seating area is visible in the background, all overlooking the serene lake and lush greenery.
Home in Berrien Springs
4.91 out of 5 average rating, 129 reviews

Lake House Retreat with a Pool

Top guest favorite
A cottage surrounded by lush trees features a spacious wooden deck with a gentle ramp. The structure's sloped roof and various window designs contribute to its unique charm. Grass covers the property, providing a natural, serene setting.
Home in Rolling Prairie
4.96 out of 5 average rating, 200 reviews

Pure Michiana - Rustic & Cozy - near the stateline

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, 427 reviews

Pet friendly, lakefront home w/kayaks & pontoon!

Guest favorite
An outdoor fire pit area is surrounded by six teal chairs, arranged in a circular formation on a stone patio. The backdrop features a cozy brown cottage partially shaded by tall trees, with a gas grill visible nearby.
Cottage in Michiana Shores
4.96 out of 5 average rating, 176 reviews

Lock In Your Fall Escape @ The Birchwood Cottage!

Guest favorite
A spacious living area showcases a light-colored sectional sofa adorned with plush pillows. Large windows allow natural light to fill the room, revealing wooden flooring and eye-catching artwork on the walls. A dining table is visible in the background, complemented by a minimalist plant.
Home in Michigan City
4.98 out of 5 average rating, 290 reviews

House of Zen: Peaceful Modern Cabin on Tryon Farm

Guest favorite
A garden pathway leads from the house to the beach, surrounded by lush trees and colorful blooms. A charcoal grill is visible on the patio, and gray steps ascend towards the entrance. The tranquil Lake Michigan is seen in the background through the foliage.
Apartment in Stevensville
4.92 out of 5 average rating, 806 reviews

Quiet Grand Mere Coach House on Lake Michigan

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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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