Vacation rentals in Lakeside

4.9 out of 5 average rating, 371 reviews

The image captures a serene beach scene at sunset, with soft sand and gentle waves. Tall grasses frame the foreground, leading the eye toward the calm water reflecting the warm hues of the setting sun and a lighthouse silhouette in the distance.

Home in Michigan City

Best Deal In Michigan City 1.3 miles to Beach

Quiet for a well deserved nights rest. Plenty of space for 4-8 guests indoors and out. Short drive to the Washington Park beach & zoo Walking distance to south shore train for a quick ride into the heart of Chicago. Less than a mile from uptown arts center and district Short drive to The National Lakeshore, that has great beaches, hiking, and biking trails! Have a day in the sun, and come back to relax, in a quiet backyard patio area equipped with grill & night lighting... Must be 24 to book

4.98 out of 5 average rating, 220 reviews

A cabin-style home is nestled among tall pine trees, featuring a large facade with distinctive tall windows that allow natural light to flood the interior. Colorful chairs are positioned on the screened porch, surrounded by well-maintained greenery and flower beds.

Cottage in Union Pier

"The Pines" in Union Pier: Year-round getaway

Under towering pine trees that feel more like the Northwoods, you're in the heart of Harbor Country. About 1.25 miles from the shore, minutes from New Buffalo & Three Oaks. Newly updated cabin-style home offers rustic feel with luxury comforts & highspeed WiFi, and great indoor & outdoor space. Garage plus add'l parking. Enjoy the area's beaches, restaurants, outdoor activities, breweries & wineries. Southwest Michigan at it's best! Please see policies for pets & children in house rules.

4.99 out of 5 average rating, 104 reviews

A spacious living area features natural light from large windows, highlighting a comfortable leather couch and a round coffee table. A decorative rug adds warmth to the wooden floor, complemented by a television and potted plant. Dining and relaxation spaces are seamlessly integrated.

Home in Coloma

Hot tub & sauna, pet friendly, 1/2m to Hagar Beach

Peaceful, newly renovated 1930’s cabin walkable (1/2 mile) to Hagar Beach in the heart of SWMI. This pet-friendly home has a cozy feel with an outdoor hot tub, sauna, & fully-furnished spaces perfect for a relaxing getaway, remote work, or staycation home base while you explore the lake, bike trails, breweries, & eateries. Enjoy a quiet, off-the-beaten path stay close to everything Lake Michigan offers featuring a stocked kitchen, cozy reading nook & desk, and outdoor dining & fire pit.

5 out of 5 average rating, 110 reviews

Home in Grand Beach

Superhost, hot tub, golf cart, fire pit, large!

Newly renovated 5 bed, 2 bath home in the quaint village of Grand Beach. Golf cart included with rental (in season - May thru mid-Nov). Home is situated on a large lot, high on a sand dune that overlooks the 6th fairway and park area. Enjoy two large decks and year-round eight person hot tub. The property is very private, on secluded street and fully stocked for a great stay. It's a great place to enjoy some down time in an idyllic village in the heart of Michigan's "Harbor Country."

4.89 out of 5 average rating, 113 reviews

A serene view of the beach extends to the horizon, where gentle waves meet the sandy shore. Lush greenery frames the foreground, leading to a tranquil expanse of water under a partly cloudy sky.

Home in Michigan City

Roomy and Private Getaway for Families & Friends

Perfect for Gatherings, Families, Birthdays, Group Outings: Enjoyment & Tranquility in Nature. Nestled on two acres of picturesque land, the property boasts a fully-equipped six-bedroom house. Conveniently located within a 5-minute drive to popular attractions such as the beach, casino, and outlet mall. Formerly a church, the house has been transformed into an inviting Airbnb rental, featuring a renovated interior, fire pit, gazebo, and many amenities.

Apartment in Michigan City

A sunset over Lake Michigan is captured through silhouetted trees. The sun's reflection glimmers on the water, creating a serene atmosphere. The peaceful scene is framed by a wooden railing, emphasizing the natural beauty of the lakeside setting.

4.94 out of 5 average rating, 136 reviews

Charming apartment in Arts District

Walk to outlet mall, art galleries, parks, restaurants, and Lake Michigan beach. Walk or drive to casino. This is a 2nd-story apartment in Michigan City's historic homes. A full 1,400 sq ft of space! Fully appointed, clean and beautifully decorated. Newly renovated kitchen and bath. WIFI. Access to beautiful back yard patio and deck. Great proximity to attractions. Great for couples, solo adventurers, and families with children.

4.99 out of 5 average rating, 267 reviews

The exterior of the cabin is framed by lush greenery, showcasing rustic wooden siding with bright red window shutters. A cozy seating area with white Adirondack chairs is positioned near the entrance, complemented by a decorative trellis and vibrant flower beds along a curved path.

Cabin in Benton Harbor

Charming Cabin-Private Beach & Golf

Why the rave reviews? This cabin is a unique and charming 2 bedroom retreat that sits atop a hill and is surrounded by elegantly sculpted terrain of Harbor Shores golf course and walking trails. The private beach on Lake Michigan is steps away. It is located in a quiet neighborhood and is close to family fun activities in St. Joe/Benton Harbor, fantastic restaurants, wine tasting, art galleries and quaint shops.

4.98 out of 5 average rating, 136 reviews

An outdoor patio area is depicted, featuring a fire pit surrounded by four chairs. A picnic table is positioned nearby on a cement surface, complemented by grassy patches and trees in the background, creating a serene rural setting.

Home in Benton Harbor

Country home near 6 beaches and Harbor Shores Golf

Convenient and close to the following attractions: Harbor Shores Golf Club - 4.9 mi Silver Beach County Park - 7.2 mi Tiscornia Park Beach - 7.0 mi Roadside Park Beach - 5.5 mi Rocky Gap Beach - 4.9 mi Hagar Park Beach - 3.0 mi Riverside Kayak Park - 2.0 mi Opening Fall 2019 Third Coast Paddling - Kayak Rental, Paw Paw River - 5.9 mi Whirlpool Corporation Headquarters - 3.5 mi

4.94 out of 5 average rating, 181 reviews

A charming cottage exterior is presented, featuring a welcoming front porch with comfortable seating. Vibrant greenery and colorful flowers enhance the landscaped yard. Large windows allow natural light to fill the space, highlighting the inviting entrance and peaceful surroundings.

Cottage in Coloma

Lake View Cottage

Adorable cottage in Coloma with a Lake View of Little Paw Paw Lake, and only 2 houses away from lake access. Public boat launch 2 mins away . Plenty of room in extra lot for your boat/ trailer Cottage comfortably sleeps five adults or 4 adults 2 kids.. Keyless entry for easy access. Coloma is so close to several Lake Michigan beaches /wineries /breweries and you pick farms.

4.91 out of 5 average rating, 112 reviews

A circle of Adirondack chairs surrounds a central fire pit, positioned on gravel. Potted plants and flowers add greenery, while a backdrop of trees and a storage shed enhance the natural setting of the outdoor space.

Cottage in Three Oaks

Private, Sun-filled Union Pier Cottage

Sunny, private cottage set on a half-acre facing woodlands. Quick drive to everything - beaches, hiking, restaurants, wineries, breweries, etc. High-speed internet available and desk with two monitors. Please be advised: reservation requests from first-time AIRBNB renters will be declined. You must have rented through AIRBNB in the past and received a high rating.

4.92 out of 5 average rating, 104 reviews

A spacious screened-in porch is presented, featuring a wooden floor and exposed beams overhead. Large windows on three sides allow natural light to flow in, offering views of the surrounding neighborhood. Two wicker chairs and a small table are arranged for relaxation.

Townhouse in New Buffalo

Downtown NB! Walk Everywhere! Huge screened porch

If you want to be in middle of everything with ample off street parking walking distance to everything you’ve found it! This is a two story two bedroom two bathroom recently remodeled unit. Perfect for 2-6 Primary has a Queen Twin over twin guest Twin over full guest Full size pull out couch in main level. Recently remodeled 2 Large flat screen tv

4.95 out of 5 average rating, 149 reviews

A charming yellow cottage is framed by a white picket fence and greenery. An American flag decorates the front, while a welcoming pathway leads to the entrance. Large windows with shutters provide light to the interior, complemented by a modest porch and seating.

Cottage in New Buffalo

The Lemonade Cottage, New Buffalo. Walk to beach!

You'll fall in love with this cute and inviting cottage. From the white picket fence to the updated kitchen and bath...you won't be disappointed. Enjoy the beautifully secluded back yard with hot tub, gazebo, grill and fire pit. Walking distance to downtown, shops, bars, restaurants, beach, marina, brewery, Redamaks, StrayDog and much more.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Houses

A space thats all yours, with room for everyone

Popular amenities for Lakeside vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Lakeside's top sights

Blue Plate Cafe25 locals recommend

Flagship Fish Market24 locals recommend

Lakeside Antiques16 locals recommend

Hearthwoods Custom Furnishings5 locals recommend

AP Shop5 locals recommend

Frecklefarm3 locals recommend

House rentals in Lakeside

4.95 out of 5 average rating, 123 reviews

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

Great Living Too

5 out of 5 average rating, 3 reviews

The exterior of a charming two-story home is showcased, featuring large windows that allow natural light to enter. A wrap-around deck with an umbrella offers outdoor seating, surrounded by well-maintained grass and shrubbery. The street is visible with a nearby view of the beach.

Home in Saint Joseph

Rhain Rentals 3 Bed in St. Joe

A private backyard features a stone fire pit surrounded by red cushioned seating. A dining table with chairs sits under a patio umbrella, and a gas grill is positioned nearby. Lush green grass and trees provide a natural backdrop.

4.89 out of 5 average rating, 114 reviews

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

4.81 out of 5 average rating, 394 reviews

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

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

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.

4.86 out of 5 average rating, 166 reviews

Irish Retreat

4.92 out of 5 average rating, 314 reviews

Home in New Buffalo

New Buffalo / Farmesque with a splash of modern

A historic house features a stone and siding exterior with a covered front porch. The entrance is framed by columns, and a pathway leads to the front door. Windows with a decorative upper design provide natural light to the interior.

5 out of 5 average rating, 4 reviews

Long-Term Spacious House for Rent

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.

4.88 out of 5 average rating, 153 reviews

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

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Cottage rentals in Lakeside

4.89 out of 5 average rating, 122 reviews

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

Charming Cottage on the Lake

4.96 out of 5 average rating, 248 reviews

An entrance area is visible, featuring a wooden cabinet displaying various dishes and decorative items. A sliding black door leads to additional spaces. Light-colored walls and hardwood flooring complement the warm wooden tones, while a bar stool is situated next to a kitchen counter.

Cottage in Union Pier

Harbor Country Michigan Hide-Away

4.95 out of 5 average rating, 198 reviews

The exterior of the cottage showcases a spacious deck adorned with colorful Adirondack chairs. Large glass doors reflect the surrounding greenery, while landscaped flower beds provide a vibrant touch. A gas grill is visible near the deck, enhancing the outdoor gathering space.

Cottage in Bangor

Van Auken Lake cottage rental

4.95 out of 5 average rating, 512 reviews

The cottage exterior, framed by trees, features a charming pergola with string lights. Several Adirondack chairs are positioned near the lush green lawn, inviting relaxation. A cozy hammock hangs nearby, enhancing the outdoor experience, along with a visible firepit area perfect for gathering.

Cottage in Goshen

Cozy, Quiet Cottage with so much Character! Clean!

4.91 out of 5 average rating, 104 reviews

A wooden dock extends over the calm lake, leading to a cottage surrounded by tall trees. Blue paddle boats are positioned on the shore, and the cottage features large windows that reflect the natural surroundings, with a peaceful yard visible in the background.

Cottage in Dowagiac

The Lakeshore

4.96 out of 5 average rating, 200 reviews

Cottage in Union Pier

Designer Cottage Relax Beach Pool & Spa—Windjammer

4.93 out of 5 average rating, 411 reviews

Large windows provide a scenic view of Flint Lake and a deck area featuring an umbrella and lounge chairs. Soft sunlight filters through the trees, illuminating a cozy seating area adorned with floral cushions.

Cottage in Valparaiso

The Lake Escape -Cozy Lakefront Cottage Valparaiso

Cottage in Lake Michigan Beach

A sandy beach is seen leading to calm waters, with Hagar Park signage positioned at the top of wooden stairs. The shore is tranquil, marked by gentle waves and a stretch of the light grey shoreline, while overcast skies create a serene atmosphere.

4.79 out of 5 average rating, 163 reviews

Sand Castles Cottages #7 Tiny House 1 Mile Lake MI

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Lakeside fishing vacation rentals

4.94 out of 5 average rating, 127 reviews

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

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

4.9 out of 5 average rating, 49 reviews

A fire pit surrounded by two chairs is positioned on a grassy area near the lake. A wooden dock extends into the calm water, with colorful trees lining the shore visible in the background under a clear blue sky. The scene reflects a serene lakeside atmosphere.

Cottage in Dowagiac

Stylish Lakehouse, Sandy Beach Includes lux Boat!

Guesthouse in Berrien Springs

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.

4.92 out of 5 average rating, 246 reviews

Make Lasting Memories at Beautiful Lake Chapin

4.94 out of 5 average rating, 93 reviews

The exterior of a charming cottage is visible, featuring a sloped roof and a large porch with clear glass windows. Colorful chairs are arranged outside on the porch, overlooking a well-kept grassy yard. Surrounding homes are partially visible in the background.

Cottage in Decatur

Lakeside Getaway

4.97 out of 5 average rating, 316 reviews

Cabin in Hartford

Secluded Log Home - Private Lake!

5 out of 5 average rating, 9 reviews

A sunlit sunroom features large windows that allow natural light to fill the space. Comfortable seating is arranged, including a spacious couch and armchairs. A small table occupies the center, while a television is mounted on the wall. A welcome mat greets visitors at the entrance.

Cottage in Eau Claire

Channel House on Indian Lake

4.9 out of 5 average rating, 21 reviews

A cozy living area features a leather sofa and a patterned chair, offering comfortable seating. Large windows allow natural light to fill the space, showcasing views of Paradise Lake. A small side table holds a laptop and decorative items, enhancing the inviting atmosphere.

Cottage in Vandalia

Private Vandalia Beach Front Cottage