Vacation rentals in Lakeside

4.99 out of 5 average rating, 525 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.

5 out of 5 average rating, 275 reviews

The open main living area features a stone fireplace underneath a wooden mantel. A circular dining table is set near large windows, while a plush sectional sofa and unique coffee table enhance the cozy atmosphere. Natural light floods the space, accentuating earthy tones.

Cabin in Michiana

Romantic Getaway in the Dunes for a Couple—Hüüsli

Cozy, charming, romantic and modern. Huusli is the perfect place for a couple to getaway, not too big, not too small. Soaring ceiling with wood burning fireplace greets you in the main living area with an updated kitchen, remodeled bathroom and two adorable bedrooms. Bonus is the four-season room where you can have all your meals or enjoy your morning coffee surrounded by nature, but without the fear of bugs. Make new memories, celebrate an anniversary or just relax in this magical place.

4.93 out of 5 average rating, 100 reviews

A modern bedroom features a spacious bed with a gray quilted coverlet and a mix of decorative pillows. A striking wall art piece is displayed above the bed, complemented by a mounted decorative deer head. A textured rug and a metal folding chair are visible in the room.

Home in Union Pier

Designer's Own Cozy Cottage

Kick back and unwind in this stylish getaway, ideally located in Union Pier and just a five-minute drive to New Buffalo. Tucked on the lake side of Red Arrow Highway, the Casita offers the perfect balance - close to all the action, yet a quiet retreat to call your own. Guests love visiting nearby beaches, indulging in baked goods, ice cream, local restaurants and wineries. Bike trails, hiking, pickle ball, golf and kayaking all nearby. Endless opportunities for relaxation and adventure await!

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.

4.91 out of 5 average rating, 130 reviews

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.

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.

4.9 out of 5 average rating, 194 reviews

Camp Wanderlust-Cozy lodge-20 minute walk to beach

A place to wander with the ones whose company you enjoy. Enjoy a cozy getaway, in our quiet cottage. 10 minute walk from shops and brewery and restaurants of Union Pier. 10 minute walk to Winery Tasting. 20 minute walk to Townline Beach. Union Pier is the perfect beach town in the heart of harbor country, enjoy exploring this magical region or maybe just kick back and build a fire and enjoy the space. 1914 a colony of Chicago bohemians, vacationed at the "Camp's Cottages" at Union Pier.

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.

4.99 out of 5 average rating, 157 reviews

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.

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, 254 reviews

"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. Updated cabin-style home offers rustic feel with luxury comforts & highspeed WiFi, and great indoor & outdoor space. Garage plus additional 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, 153 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.

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, 384 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!

4.97 out of 5 average rating, 178 reviews

A spacious screened-in porch is adorned with comfortable seating and decorative pillows. Large windows allow natural light to fill the area, while a decorative table at the center holds a selection of refreshments. The serene view of the surrounding landscape enhances the inviting ambiance.

Cottage in Sawyer

Hot tub open year round in modern/rustic cottage!

Kick back and relax in this rustic & stylish cottage that is surrounded by gorgeous landscaping on almost 2 acres in Harbert. Cherry Beach a 5 min drive, 15 mins to New Buffalo, & minutes to Greenbush, Infusco, Susan's & the new Out There wine bar! Perfect place if you seek peace & quiet - play a record, hit the hot tub, read a book in screened in porch or hammock, hang out by the firepit or jump on one of the 4 bikes! So close to boutiques, coffee shops and cute restaurants!

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, 345 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!

4.95 out of 5 average rating, 370 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. Kids accepted.

Popular amenities for Lakeside vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Lake side house rentals in Lakeside

4.97 out of 5 average rating, 109 reviews

A comfortable living room is highlighted by a spacious sectional sofa with decorative pillows. A light-finished wooden coffee table sits on a soft area rug featuring warm tones. Natural light enters through a large window, complemented by sheer curtains, while a ceiling fan adds a functional design element.

Home in La Porte

La Casita De Lago

4.95 out of 5 average rating, 220 reviews

A stylish living area features a blue sofa with throw pillows, situated on a patterned rug. Natural light streams through a skylight, illuminating the open layout that includes a dining space and kitchen with modern appliances. Minimalist decor enhances the inviting ambiance.

Home in New Buffalo

Steps to Beach & Starbucks! Private Yard, Firepit!

4.96 out of 5 average rating, 127 reviews

A light-filled living area features a comfortable sofa adorned with decorative pillows. A wooden coffee table sits in the center, placed on a soft area rug. Large windows allow natural light to stream in, highlighting the open floor plan that leads to the kitchen.

Home in New Buffalo

Lux home, sauna, hot tub, firepit, 5 min to beach

4.98 out of 5 average rating, 237 reviews

Home in La Porte

Aunt Betty's Lakeside Abode, Hot Tub Steam Shower

4.96 out of 5 average rating, 27 reviews

Home in Sawyer

Wishing Well Cottage

4.97 out of 5 average rating, 231 reviews

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

The Walnut House, Michigan Woods Retreat

Superhost

Home in Three Oaks

4.87 out of 5 average rating, 141 reviews

Pool Opens May 25! | Hot Tub • Walk to Lake

A modern cottage is set in a lush green landscape, surrounded by trees and shrubs. The structure features large windows and a welcoming front porch, complemented by a manicured lawn and varied plant life. Sunlight creates a warm atmosphere throughout the scene.

4.88 out of 5 average rating, 41 reviews

Updated, bright and peaceful cottage in Lakeside

Other great vacation rentals in Lakeside

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.

4.98 out of 5 average rating, 91 reviews

The Honey Bee Lakeside

5 out of 5 average rating, 27 reviews

A private pool area features a sparkling blue pool with a shallow entry and a floating pool lounge. Six lounge chairs are positioned under large umbrellas on a sun-soaked patio, offering shaded spaces for relaxation. The surrounding green trees provide a serene backdrop.

Home in Three Oaks

Updated Lakeside | Pool (Open!) + Hot Tub + Porch

4.98 out of 5 average rating, 42 reviews

A rustic living area features a wooden fireplace surrounded by stone tiles, with a circular mirror above it. A flat-screen TV is mounted on the wall, and stacked firewood is neatly arranged beside the fireplace. A wooden cabinet and decorative items add charm to the space.

Cottage in Lakeside

Cozy Lake House with Bonus Guest Cottage!

4.98 out of 5 average rating, 82 reviews

The exterior of the Black Barn features a modern architectural design with triangular windows and a dark wood facade. Surrounded by a grassy area and trees, a tranquil setting is presented that integrates the structure into the natural environment.

Farm stay in Buchanan

Verdant Hollow Farm Stay-Tigerman Black Barn

4.92 out of 5 average rating, 13 reviews

Lee's Cottage in Lakeside

5 out of 5 average rating, 12 reviews

Home in Union Pier

Harbor Country Poolside

4.92 out of 5 average rating, 12 reviews

A modern kitchen is showcased, featuring light blue cabinetry and a marble-topped island. A wooden stool is positioned at the island. Fresh flowers sit in a vase, adding a natural touch. Large windows allow ample light, with soft gray curtains framing the view.

Cottage in Lakeside

(Unit A) Lakeside Charmer Steps To Association

A wooden deck is shown with a table and four chairs, each adorned with floral cushions. Lush green trees provide natural shade, and a view of Lake Michigan is visible in the distance, creating a serene outdoor setting.