Vacation rentals in Lakeside

4.99 out of 5 average rating, 110 reviews

A spacious living area features large French doors that open to a deck. A neutral-toned sofa is adorned with decorative pillows, while a wooden coffee table sits in front. An inviting armchair and framed artwork complement the warm, natural lighting filtering in.

Cottage in Sawyer

The Cottage of Harbor Country - Close to it all!

Welcome to your very own Cottage in Harbor Country! The perfect weekend getaway from Chicago, our cottage is close to Warren Dunes and just a 15-20 minute walk to Lake Michigan. Renovated and beautifully appointed, it blends vintage charm with modern updates! Enjoy morning coffee on the new deck or screened-in porch, take a dip in the new hot tub, or cozy up next to the wood-burning fireplace. Enjoy the perfect place to relax, hike, go antiquing, wine-tasting, and make memories with loved ones!

4.95 out of 5 average rating, 364 reviews

The cabin is nestled among lush trees, with soft outdoor lighting illuminating the entrance. Large windows reveal a welcoming interior glow, while a small outdoor seating area is visible nearby, blending seamlessly into the surrounding natural environment.

Cabin in Union Pier

McComb's Cabin, Union Pier, MI

Giant trees welcome you down the drive back to the cabin in the woods. The cabin, along with my house and a small cottage reside on the 2 1/2 acre property. A contemporary cabin of steel and pine with vaulted ceiling and sky lights. Open living space, inviting queen size bed, luxury rain shower, full kitchen but no stove. A wood burning fireplace- fall through end of March and outside fire pit. Public beach a 5 minute drive away. Couples check out the cabin for anniversaries & special days.

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.

4.98 out of 5 average rating, 321 reviews

House of Zen: Peaceful Modern Cabin on Tryon Farm

The House of Zen is an architect designed home situated in the woods, part of a sustainable farm community on 170 acres. Only an hour drive from Chicago, and close to Indiana Dunes National Park, it is the ultimate escape. The perfect getaway for couples, creatives and nature lovers who want some peace, quiet and space. Explore the farm trails & enjoy the wildlife and soothing sounds. Note: We have a 3 night minimum stay during summer, but open up 2 night stays 1-2 weeks before if possible.

4.97 out of 5 average rating, 239 reviews

Home in Three Oaks

Casa Gitana - Boutique Style Stay in Three Oaks

Casa Gitana is a Boutique style stay in the quaint town of Three Oaks, MI. Just a short drive to the pristine beaches of Lake Michigan and walking distance to downtown, our home offers an eclectic & contemporary feel that is perfect for a relaxing getaway any time of the year. We personally manage & oversee the home before every stay, & take pride in putting thought & intention into every detail. We want our guests to feel at home, and most importantly enjoy a comfortable and relaxing stay. :)

4.93 out of 5 average rating, 193 reviews

A spacious yard is enveloped by trees, providing a natural setting for relaxation. A deck and seating area are visible, along with a house featuring large windows and a welcoming entrance. The greenery and sunlight create an inviting outdoor atmosphere.

Home in Lakeside

Annie's Attic

A great place for family/friends to gather. A cozy, comfortable house in Harbor Country - accommodations for a week, a few days or a weekend of fun all year long. The natural setting can be an escape includes a large deck/yard to relax or light a small fire. Enjoy a beach day(a few beach chairs available to rent during your stay)or explore the area. Annie's Attic is close to beaches, state parks, wineries, breweries, restaurants, local wedding venues, antiques, & shops. So much to love here!

4.99 out of 5 average rating, 153 reviews

The exterior of the cozy Tree House is highlighted, featuring a spacious deck with rocking chairs. Mature trees surround the cottage, which showcases a warm exterior design. A well-maintained garden with shrubs and decorative plants enhances the inviting atmosphere.

Home in Lakeside

Lakeside Retreat Nestled Among the Trees

Please note: Summer stays are 7 night minimums from Friday to Friday. Welcome to our cozy 'Tree House,' nestled among the trees in Lakeside, Michigan! Our renovated cottage is 90 minutes from Chicago in the heart of Harbor Country. Our bright, open home features high end finishes and luxury mattresses. Nature-inspired hues invite you in, making relaxation a top priority! Generous outdoor spaces include a deck with dining area, rocking chairs, and two fire pits for s'mores under the stars.

4.81 out of 5 average rating, 118 reviews

A spacious living room is filled with natural light from a large window. A comfortable gray sofa, red armchair, and black accent chair are arranged around a glass coffee table. A fireplace is set against an attractive wall, and a television is mounted above it.

Apartment in Bridgman

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours

Welcome to "Lake 2 Grapes" Bridgman is a little gem located between St. Joe and Warren Dunes. Minutes to Lake Mi. beaches, craft breweries, and wine trails. Relax in the upper level of our bi-level vacation home w/private entrance. This 3 bedroom, 2 bath includes a beautiful Master suite! Enjoy the Hot tub and fire pit in the backyard. Wine Tour? Stay with us and you'll receive a discount with "Grape & Grain Tours" plus complimentary pick up and drop off. Must be 25 or older to book.

4.99 out of 5 average rating, 132 reviews

A cabin exterior is presented, featuring a screened-in porch that offers comfortable seating. The structure, painted in a muted green tone, is surrounded by trees and foliage. A set of steps leads to the porch, creating easy access to the welcoming retreat.

Cabin in Union Pier

Walk 2 Lake/Shops | Hot Tub | King Bed | Fireplace

Tucked away sophisticated cabin in the heart of Downtown Union Pier. Killer location that's just steps away from dining and drinks: Black Current Bakery, Neon Moon Gelato, Union Pier Market, and Union Pier Social. Townline Beach is a 10 minute walk, and the cabin is right off the bike path. Seeds Brewery is just down the road and local Wineries are 1 mile away. Back home enjoy a relaxing hot tub (available year round), wood burning fire place, spacious screened in porch & outdoor fire pit.

5 out of 5 average rating, 140 reviews

A bright living area features a comfortable gray sofa adorned with decorative pillows, paired with a light brown armchair. Large windows provide views of lush greenery, while a striped rug anchors the space. A coffee table with a bowl sits at the center, enhancing the cozy atmosphere.

Home in Sawyer

The treehouse at Warren Dunes

Looking for the perfect Harbor Country getaway? We've got you covered! Just 90 miles from Chicago and adjacent to Warren Dunes State Park, this beautifully remodeled home hidden in the trees is the perfect escape. With accommodations up to 6 on four levels of living space, you'll enjoy an indoor/outdoor living experience like no other. Conveniently just 200 yards from the beach with walking path access at the end of the street and easy access to all the activities this area has to offer.

A charming cottage is surrounded by lush green landscaping and vibrant flowers. A screened-in porch is adorned with lights, leading to an inviting entryway. A separate storage garage is visible in the background, complementing the colorful exterior of the cottage.

4.94 out of 5 average rating, 374 reviews

Steps to the Beach! Screened in Porch & Firepit!

Experience the ultimate Harbor Country getaway! Just a 90-second stroll to a public beach access and under 5 minutes to another, this location is unbeatable. Spend your day soaking up the sun, kayaking, paddle-boarding, antiquing, golfing, or climbing majestic dunes. Discover endless local breweries, wineries, and top-rated restaurants. Unwind in the evening on the spacious screened-in porch or by the cozy firepit. Your perfect retreat awaits - adventure and relaxation all in one!

4.89 out of 5 average rating, 120 reviews

Two white Adirondack chairs are positioned adjacent to a circular fire pit. The ground is covered with colorful fallen leaves, and trees with yellow foliage provide a natural backdrop. The scene reflects a serene outdoor space ideal for relaxation.

Apartment in Sawyer

Morton's Retreat Cozy 1 Bedroom Apartment

Cozy comfort close to Michigan's most popular state park, breweries, wineries, antique malls and farm-to-table restaurants. Morton's Retreat has plenty of room to relax. Charcoal grill and fire pit (shared with Morton’s other retreat) for use in a spacious yard. Private entrance with keyless entry makes check-in a breeze. One other Airbnb located next door in same building. Two complimentary local beers, seltzer water and a snack are provided to help kick off your stay.

An inviting cottage exterior features a wooden fence and a screened porch. Surrounding greenery showcases tall grasses and autumn foliage, creating an appealing atmosphere. A chimney and part of the roof can be seen, indicating the cozy interior space.

4.95 out of 5 average rating, 332 reviews

J’s Beach House: Hot Tub & short walk to beach!

J's Beach House is < a 5 minute walk to the beach! My cottage is equipped with a private hot tub and fireplace. Enjoy the walkable town or jump in your car for a quick drive to any Harbor Country activity! Potential for rental with adjacent cottage "Riley's Retreat". *Please inquire about our other Airbnb cottage near downtown Union Pier. This cottage is a 2-bedroom plus kids loft, screen porch, hot tub, fire pit, plus walking distance to Townline Beach!

Popular amenities for Lakeside vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Lakeside cottage rentals

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.

4.97 out of 5 average rating, 150 reviews

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

Cottage in Michiana Shores

4.99 out of 5 average rating, 149 reviews

The Pines Cottage on Birchwood

4.86 out of 5 average rating, 198 reviews

An outdoor area is shown featuring a hot tub positioned on a wooden deck. The red exterior of the cottage contrasts with the surrounding green grass and wooden fencing. A glass door leads into the main structure, enhancing the inviting rural charm.

Cottage in Benton Harbor

Hot tub! Red Tin Cottage of Harbor Country!

4.98 out of 5 average rating, 214 reviews

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

New Buffalo retreat - Perfect year-round getaway!

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.

4.97 out of 5 average rating, 230 reviews

Designer Cottage Relax Pool Beach & Spa—Windjammer

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.

4.98 out of 5 average rating, 247 reviews

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

4.82 out of 5 average rating, 187 reviews

The living room features a white couch adorned with bright cushions, a mint green coffee table, and a standing lamp. Natural light fills the space through large windows dressed with sheer curtains. A welcoming entryway is visible, complemented by decorative wall accents.

Cottage in Elkhart

Peach Beach Cottage at Simonton Lake! 2 Bed/1 Bath

Superhost

Cottage in Three Oaks

4.82 out of 5 average rating, 196 reviews

Hot Tub • Sauna • Fireplace | Cozy Winter Retreat

Lakeside house rentals

Superhost

A hot tub is positioned in a grassy area, surrounded by a white fence. It features a raised, circular design with a protective cover partially open. A set of steps leads up to the tub, positioned adjacent to a bright blue Adirondack chair.

4.93 out of 5 average rating, 110 reviews

Duplex | Firepit | Game Room | Hot Tub-all year

4.87 out of 5 average rating, 308 reviews

The exterior of the newly remodeled home showcases a neatly arranged wooden deck with a railing. Comfortable outdoor furniture is positioned on the deck, while well-maintained greenery surrounds the home. A gentle slope leads to the entrance, enhancing accessibility.

Home in South Bend

Home newly remodeled minutes from Notre Dame.

4.96 out of 5 average rating, 196 reviews

A comfortable living area is presented with a light grey sofa adorned with blue accent pillows. A glass coffee table sits in front, displaying a few books and decor. A television is positioned on a wooden media console, with warm natural light coming through large windows.

Home in Three Oaks

The Getaway - Hot Tub - 3 BR 1.5 Bath

4.97 out of 5 average rating, 253 reviews

Visit LakeMichigan Beach-Brewery-Casino-OutletMall

4.95 out of 5 average rating, 194 reviews

A fire pit surrounded by six chairs is set in a pebbled area, with a spacious yard and a blue house in the background. The house features a deck with seating and is framed by trees, creating a secluded atmosphere.

Home in Sawyer

Darling Home + Hot Tub by Warren Dunes + Wine Bar

A cozy living room features a brown sofa with decorative throw pillows and a teal upholstered ottoman. A wooden coffee table sits on an area rug, while large windows provide natural light and outdoor views. A gas fireplace is visible against a textured blue accent wall.

4.92 out of 5 average rating, 203 reviews

Pet Friendly, Fenced Yard, and Hot Tub Getaway

4.91 out of 5 average rating, 127 reviews

A charming cottage is depicted with a large deck featuring outdoor seating and a blue umbrella. The surrounding area showcases a well-maintained lawn and lush trees, with a barbecue grill visible in the background.

Home in Lakeside

Secluded Garden New Buffalo/Lakeside MI

4.87 out of 5 average rating, 186 reviews

The cottage features a welcoming facade with blue shutters and a vibrant red front door. A decorative flag is displayed on the porch railing, surrounded by neatly manicured greenery and blooming flowers, contributing to the inviting outdoor space.

Home in Stevensville

Cheerful 3BR 2BA Country Cottage Near Attractions

Lakeside fishing vacation rentals

Farm stay in Michigan City

An outdoor area is illuminated with colorful lights, featuring a wood-fired hot tub and a seating arrangement. Inside, the cozy living space showcases a deep blue sofa, a dark wood coffee table, and a kitchenette with modern appliances, ensuring a comfortable atmosphere.

4.96 out of 5 average rating, 363 reviews

Northstar Retreat & Wood Fired Hot Tub

4.88 out of 5 average rating, 134 reviews

The exterior of a charming barn-style home is showcased, featuring a distinctive arched roof, large double doors, and black shutters. Two potted plants frame the entrance, with a welcome sign visible above the door. A grassy area and gravel pathway lead to the entrance.

Barn in Three Oaks

Barn of Three Oaks near Lake Michigan/Journeyman

4.95 out of 5 average rating, 222 reviews

The cabin's exterior is framed by colorful autumn foliage, with vibrant red leaves and dappled sunlight filtering through the surrounding trees. Stone steps lead to the entrance, enhancing the rustic charm of the well-maintained landscape.

Cabin in Michiana

Luxury Cabin Getaway •2 min to Beach• 1hr Chicago

4.83 out of 5 average rating, 104 reviews

An open living area features a casual dining table surrounded by four chairs and a kitchen bar with seating for four. Large windows and glass doors allow natural light to brighten the space, while a red leather armchair and a blue accent chair invite relaxation.

Home in Three Oaks

Three Oaks Creek House Perfect

4.89 out of 5 average rating, 145 reviews

A quaint cottage is nestled among towering pine trees on a spacious, lush lawn. A stone pathway leads to the entrance, framed by a serene natural setting filled with greenery and shaded by the surrounding trees.

Guesthouse in Sawyer

Lola's Pine Tree Cottage

4.93 out of 5 average rating, 228 reviews

A cozy living area features a gray sofa adorned with patterned cushions, complemented by a pair of leather chairs. Natural light floods through large windows, illuminating the hardwood floor. A coffee table sits at the center, while a flat-screen TV is mounted on the wall.

Cottage in Sawyer

Bright & Warm by Warren Dunes Maple St Beach House

Apartment in Michigan City

A private balcony offers a serene space with two light-colored chairs set around a small table. A view of the surrounding neighborhood is complemented by a tree and grassy area, with the sunset colors illuminating the sky in the background.

4.9 out of 5 average rating, 212 reviews

Perfect 1 Bed Penthouse Steps To Beach w/Parking!

The dining area features a large wooden table surrounded by comfortable seating, illuminated by a modern pendant light. Nearby, the hot tub area is visible through large glass doors, nestled among lush greenery, providing a tranquil outdoor experience.