Vacation rentals in Lakeside

4.99 out of 5 average rating, 522 reviews

A charming, rustic cabin is nestled among vibrant autumn foliage, showcasing a wooden exterior and a sloped metal roof. The cabin is partially obscured by trees, with golden leaves creating a warm frame around the structure, signaling a serene woodland retreat.

Farm stay in La Porte

Cabin on Swede Hill

Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

4.97 out of 5 average rating, 194 reviews

A yurt is set amidst a green landscape, with a wooden deck leading up to its entrance. A small private outhouse is positioned nearby, adorned with flowers. Overhead, a dramatic sky features varied cloud formations, enhancing the peaceful rural setting.

Yurt in Buchanan

Off Grid Yurt Glamping on Permaculture Homestead

Stay in our stylish yurt for a one of a kind "glamping" experience on a 20acre homestead! The perfect location on the Southwest Michigan wine trail and just 15 minutes to Lake Michigan beaches! Awesome ammenities - off grid solar power, private outhouse, outdoor shower, fans, fridge, grill, firepit, and more. Take the tour, meet sheep, horeses, chickens, rabbits and learn permaculture. Order our delicious DIY pancake breakfast featuring homemade maple syrup, our organic eggs and pancake batter.

4.9 out of 5 average rating, 125 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

Enjoy every season at Dunedin Cottage, only 10 minutes from New Buffalo and in the heart of Harbor Country & the SW Michigan wineries. 3 lovely beaches in 2-3 minutes drive and parking. Great for families or groups celebrating weddings, birthdays or just relaxing. We have a fabulous garden (fully fenced) complete with fire pit, outdoor furniture, outdoor shower, large gas grill and lovely screened in patio. The fully stocked kitchen is a chefs delight complete w/ a large dining room table.

4.99 out of 5 average rating, 151 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.

4.99 out of 5 average rating, 118 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, 138 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.

Guesthouse in New Buffalo

A compact guest house features a light green exterior with white trim, set within a grassy area. A welcoming front porch includes two chairs and a small bench, surrounded by flowering plants. Large windows allow ample natural light to enter.

4.98 out of 5 average rating, 887 reviews

"Tiny House" Guest House - No Cleaning Fee

"Tiny House" guest house located under large oak trees near the beach, and not far from I-94 and the Michigan state line. Vaulted ceiling, open feeling. Light and bright décor. Full bathroom, comfy couch, and other amenities. Polished concrete floor, whitewashed shiplap ceiling, hand-crafted oak furniture, suspended shelving. High ceilings, windows with southern exposure, front porch with siting chairs and a grill. Convenient charger for electric cars. Never a cleaning fee.

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, 369 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, 118 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.

4.93 out of 5 average rating, 192 reviews

A charming cabin is nestled among tall trees, with a deck visible on one side. Surrounding areas feature mowed grass and fallen leaves, creating a tranquil rural setting. Additional structures, including a shed, can be seen in the background, adding to the serene atmosphere of the property.

Guesthouse in Sawyer

Heron's Rest Hideaway, nature lovers' dream

Privacy on 11 acres of conservancy-protected land including two small lakes, river access , woods. Rowboat available. Minutes from Michigan’s most popular beach, breweries, wineries, antique malls, farm-to-table restaurants. Fully equipped kitchen, gas fireplace. Private fire pit, deck, and gas grill. Kayak, bike, hike nearby. Separated from our home by a breezeway. Private entrance, quiet road, dark nights. Daytime woodworking noise possible. Limit of 4 guests.

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, 329 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!

4.96 out of 5 average rating, 258 reviews

A modern kitchen is visible, featuring white cabinetry and stainless steel appliances. The living area includes a comfortable couch and a round table with a decorative runner. Natural light fills the space, highlighting the open layout and ceiling beams.

Home in Lakeside

Couples alert! PVT beach access, hot tub, firepit!

ADORABLE HOME IN LAKESIDE WAS RECENTLY REHABBED & OFFERS A SUPER CLEAN AND MODERN FEEL IN THE HEART OF HARBOR COUNTRY. GUEST HAVE ACCESS TO PRIVATE BEACH WHICH IS A 7 MIN WALK AWAY - NO CROWDED BEACHES! YEAR ROUND HOT TUB, A SUPER COMFY KING SIZE BED AND ONE PULL-OUT COUCH FOR 4 GUEST (MAX). FIREPIT SUPPLIED WITH WOOD, AN OUTDOOR PATIO AND WEBER GRILL COMPLETE THIS LOFT LIKE HOME. FULLY STOCKED KITCHEN, HIGH DEF TV, STREAM MUSIC, ETC! YOU WILL LOVE IT!

Popular amenities for Lakeside vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Lakeside house rentals

4.82 out of 5 average rating, 345 reviews

A multi-level house is set on a grassy area, featuring a stairway leading to a deck adorned with flower pots. Vibrant red canopies provide shade, and bicycles are stationed nearby, creating an inviting environment. The exterior showcases a mix of wooden and painted surfaces.

Home in Chesterton

South Shore Studio Apartment {National Park}

4.95 out of 5 average rating, 196 reviews

A fenced outdoor area features a gravel surface with a fire pit and two wooden benches. A green putting green is visible on one side. A covered deck provides shade and houses a grill. Nearby, trees and shrubs enhance the natural setting.

Home in New Buffalo

Steps to Beach & Starbucks! Private Yard, Firepit!

A charming yellow cottage is surrounded by greenery and vibrant flowers. The home features blue shutters and a welcoming front porch with white railings. A paved pathway leads to the entrance, framed by well-maintained grass and landscaping.

4.99 out of 5 average rating, 152 reviews

Dog Friendly Downtown Three Oaks Cottage! Fenced!

4.95 out of 5 average rating, 187 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 comfortable living area features two black reclining chairs and a cozy sofa adorned with decorative pillows. A tasteful area rug covers the floor, while a mirror reflects natural light from a nearby window. A small shelving unit is positioned against the wall.

4.85 out of 5 average rating, 100 reviews

Cheerful home with free covered parking onsite.

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

4.9 out of 5 average rating, 237 reviews

CASA TICA Serenity Amongst Nature Dog Friendly

5 out of 5 average rating, 124 reviews

A welcoming entrance features a bright yellow door against a mint green facade. Brick steps lead to a patio area, adorned with potted plants and a vintage cooler. The sun casts a warm glow over the peaceful lakeside view.

Home in La Porte

UncleLarrysLakePlace HotTubKayaksPingPong

4.9 out of 5 average rating, 122 reviews

The log cabin features a green metal roof and a welcoming front porch with a wooden railing. The porch is furnished with chairs, and a pathway leads to the entrance. Surrounding greenery enhances the natural setting of the cabin.

Home in Sawyer

The Acorn near Warren Dunes Red Arrow Cabins

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.

4.95 out of 5 average rating, 353 reviews

Northstar Retreat & Wood Fired Hot Tub

Cottage in Michiana Shores

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.

4.99 out of 5 average rating, 146 reviews

The Pines Cottage on Birchwood

4.95 out of 5 average rating, 213 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

A spacious deck with metal furniture is surrounded by tall trees and lush greenery. A nearby screen porch offers a view of the natural setting, creating an inviting atmosphere for relaxation outdoors.

4.97 out of 5 average rating, 268 reviews

Harbor Country Michigan Hide-Away

4.93 out of 5 average rating, 449 reviews

Chalet in La Porte

Pet friendly, lakefront home directly on Pine Lake

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.

4.96 out of 5 average rating, 225 reviews

Designer Cottage Relax Pool Beach & Spa—Windjammer

Superhost

A private hot tub is visible, featuring a clear water surface and multiple jets. The tub is surrounded by a wooden deck, providing a relaxing outdoor space for guests to unwind.

Cottage in Three Oaks

4.83 out of 5 average rating, 187 reviews

Pickleball & Volleyball Nets |Hot Tub| Sauna|Beach

4.95 out of 5 average rating, 163 reviews

A private backyard features a patio space with a table surrounded by four chairs. The area is paved with stones and includes a raised wooden deck, a grill on the deck, and flower beds adding a touch of greenery. The house is painted in a warm peach color.

Home in Michigan City

Midcentury marvel steps from beach! Pups

Lakeside fishing house rentals

A light-filled living area features a cozy sofa with decorative pillows, two comfortable armchairs, and a stone fireplace. A flat-screen television is mounted on the wall, and a small table holds decorative plants. Natural light enters through multiple windows.

4.98 out of 5 average rating, 116 reviews

Harbert Woods - 5 min walk to beach!

4.89 out of 5 average rating, 139 reviews

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

Lake House Retreat on the water

4.96 out of 5 average rating, 184 reviews

The charming two-story home features a wide front porch with ample seating and decorative lighting. White railings and a wooden design enhance its appeal. Flanking trees provide some greenery, and the entryway is welcoming with its open doors and stylish decor.

Home in Michigan City

5 Bedroom Luxury Home In Heart of Beachwalk Resort

4.97 out of 5 average rating, 101 reviews

A spacious outdoor deck offers serene views of the surrounding greenery and a tranquil lake. A hammock is suspended between two trees, inviting relaxation, while potted plants add subtle touches of color to the area. The scene is illuminated by soft, natural light.

Home in La Porte

Renovated french country lake home. 6bedroom/4bath

4.98 out of 5 average rating, 125 reviews

A tranquil scene showcasing the serene waters of Lake Michigan, framed by lush greenery. The image features a private beach area with sand and a flag gently waving. A gazebo and seating around a fire pit highlight the outdoor living space, perfect for relaxation.

Home in Benton Harbor

Lake Michigan•Private Beach•Amazing View•Hot Tub

4.96 out of 5 average rating, 206 reviews

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

Pure Michiana - Rustic & Cozy - near the stateline

An updated home is positioned at the center of the image, featuring a welcoming entrance with a decorative porch and large front steps. Surrounding gardens include well-maintained shrubs and trees. The sky showcases soft pink and purple hues as daylight transitions into evening.

5 out of 5 average rating, 104 reviews

Hot tub! In the heart of Three Oaks!