Vacation rentals in Lakeside

4.95 out of 5 average rating, 367 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 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.

4.93 out of 5 average rating, 194 reviews

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!

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, 127 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 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, 156 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, 249 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, 145 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, 145 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, 378 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!

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, 151 reviews

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

Dear friends, Welcome to Beach Bird Cottage, situated on a quiet street with other vintage cottages in the heart of Union Pier. It is an easy 5-minute walk to an association beach. The cottage has many updates, including a new kitchen, bathroom, washer/dryer, outdoor shower and a wood stove. The master and second bedroom each have queen-size beds and the children's bedroom has two twin beds. Enjoy an early swim before breakfast or have an evening beach picnic under the sunset.

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, 337 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!

A modern exterior is displayed, featuring a light gray façade with white trim. Large windows and French doors provide ample natural light, framed by lush greenery. An outdoor area is visible, with a gravel path leading to the entrance, and colorful potted plants accentuate the space.

4.96 out of 5 average rating, 280 reviews

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!

4.89 out of 5 average rating, 121 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 seltzer waters and snacks are provided to help kick off your stay.

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, 103 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, 212 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!

4.94 out of 5 average rating, 126 reviews

A welcoming entrance with a dark front door is framed by white columns. The cottage features a charming combination of brown shingle siding and a stone chimney. Potted plants are positioned on either side of the doorway, enhancing the inviting appeal.

Home in New Buffalo

The Riviera Beach Retreat one mile from downtown

4.98 out of 5 average rating, 117 reviews

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.

Home in Three Oaks

Harbert Woods - 5 min walk to beach!

4.97 out of 5 average rating, 120 reviews

Home in New Buffalo

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

5 out of 5 average rating, 152 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

4.97 out of 5 average rating, 227 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

Two yellow adirondack chairs are positioned on a well-maintained green lawn, overlooking the expansive view of Lake Michigan. Bare trees line the area, and the clear blue sky reflects on the water's surface.

4.96 out of 5 average rating, 45 reviews

Enjoy your own private beach on Lake Michigan

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, 11 reviews

A tranquil setting is presented with a sandy path leading through tall grass towards a cabin nestled in the trees. The structure is partially visible, surrounded by greenery that blends harmoniously with the natural landscape.

Home in Bridgman

Dancing Waters

A spacious outdoor area is depicted, featuring multiple wooden lounge chairs arranged around a stone fire pit. Potted plants add greenery, while the house's large windows provide a glimpse of the interior. Trees surround the patio, enhancing the privacy of this inviting outdoor space.

5 out of 5 average rating, 51 reviews

Charming Cottage - Hot Tub, Sauna, Large Yard

Superhost

A bright living area features vaulted wooden ceilings and large windows allowing natural light to fill the space. Comfortable seating is provided by a sectional sofa and two patterned armchairs, with a soft rug underfoot. A flat-screen TV is mounted on the wall.

4.7 out of 5 average rating, 23 reviews

Renovated 3BR Lakefront | Balcony | Firepit | W/D

5 out of 5 average rating, 9 reviews

Home in Union Pier

Harbor Country Poolside

4.91 out of 5 average rating, 54 reviews

A well-maintained outdoor area features a gravel pathway leading to a cozy seating arrangement with four folding chairs surrounding a small round table. Vibrant pink flowers add color to the landscape, while the cottage's white exterior is complemented by large windows that provide ample natural light.

Home in Union Pier

The Luna Cottages - Unit 2 - Private Beach Access!

4.86 out of 5 average rating, 86 reviews

A fire pit area is arranged with red Adirondack chairs surrounding it, set on a gravel surface. Logs serve as natural seating. The backyard shows a mix of grass and landscaped patches, with a glimpse of the cottage and patio area in the background.

Cottage in Lakeside

The Rail House, Lakeside MI

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.