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.

4.97 out of 5 average rating, 106 reviews

The Honey Bee Lakeside

Keep it simple at this peaceful, centrally-located place. Modern and pristinely cared for home w/open floor plan offers privacy and autonomy. Close to Harbor Country beaches and amenities. Set on an acre with gorgeous screen porch to while away the afternoons, plus large deck built around a giant oak to commune with nature, and fire pit to hang with friends. Attached garage with ping pong for the youngsters and young at heart. En suite primary plus two additional bedrooms. 6 adults, 2 dogs max

LocationFamilyQuiet

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.

4.96 out of 5 average rating, 299 reviews

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

ADORABLE LAKESIDE COTTAGE W/YEAR-ROUND HOT TUB AND A GUEST FAVORITE - ACCESS TO SEMI-PRIVATE LAKE MICHIGAN BEACH SHARED BY JUST 10 HOMES SO IT'S NEVER CROWDED! BEACH ACCESS GATE IS 7 MIN WALK FROM COTTAGE. LOFT LIKE HOME IS SUPER CLEAN WITH VERY COMFY KING SIZE BED AND ONE PULL-OUT COUCH FOR 4 GUEST (MAX). FIREPIT SUPPLIED WITH WOOD, AN OUTDOOR PATIO AND WEBER GRILL - YOU WILL LOVE IT! Bike/walking path out front and just 10 mins to New Buffalo, Whistle Stop, coffee - just steps away!! HURRY!

FamilyValueBackyard

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, 137 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.

LocationValueLayout

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, 162 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.

LocationValueSleep quality

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, 264 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.

FamilyValueIndoor spaces

4.99 out of 5 average rating, 174 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.

ValueFamilyQuiet

5 out of 5 average rating, 149 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.

ValueFamilyBathroom

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, 955 reviews

"Tiny House" Guest House - Great for Couples

"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 an umbrella. Convenient charger for electric cars. Never a cleaning fee.

FamilyValueQuiet

4.97 out of 5 average rating, 199 reviews

The exterior view showcases a modern lodge-style home with dark wood paneling and large windows. A pathway leads toward the entrance, bordered by greenery. Soft lights illuminate the building, creating a warm ambiance against a backdrop of trees.

Home in Union Pier

luxe new buffalo lodge, hot tub, 12m walk to beach

Relax with family or friends at our peaceful place to stay. Located in the heart of Union Pier , walking distance to Beach and lots of attractions. Easily will sleep 16 , chill modern lodge vibe to it , high ceilings, heated concrete floors , 2500 sq ft , new construction , 5 bedroom/ 2.5 bath .Set on front porch overlooking forest year round , stroll to patio and enjoy your private hot tub . Home is spacious, 70 ft long so plenty of room to spread out and or host a large gatherings .

ValueLocationCleanliness

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, 245 reviews

Designer Cottage Relax Pool Beach & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, community pool, private hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax and unwind in this luxurious updated getaway with plenty of sun filled space for all to enjoy year-round. Professional Wolf stove for the chefs. Book your stay today! Create lasting memories!

LocationFamilyCleanliness

Guesthouse in New Buffalo

A cozy bedroom features a spacious bed adorned with layered textiles and decorative pillows. Large windows provide views of the outdoors, while natural light is enhanced by wooden ceiling beams. A small dining area with chairs and a table is positioned nearby.

4.96 out of 5 average rating, 699 reviews

Rainbows End 🌈 Plensa

Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

ValueFamilyBiking

4.99 out of 5 average rating, 109 reviews

Home in Three Oaks

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

Just a few days left this summer at Flamingo Ranch—an unforgettable retreat nestled in Harbor Country, 1/2 mile from the lake. This designer-owned haven offers both deep seclusion + an open-format layout that invites connection to loved ones and nature + memory-making. Whether you’re gathering with family, reuniting with old friends, or seeking a rejuvenating escape, we deliver an experience that’s as comfortable + stylish as it is energetically charged.

FamilyValueParks

Popular amenities for Lakeside vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Lake side house rentals in Lakeside

4.94 out of 5 average rating, 232 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!

LocationFamilyParking

4.94 out of 5 average rating, 99 reviews

A spacious living room is highlighted by tall ceilings with exposed beams. Comfortable leather seating surrounds a central coffee table, and a large television is positioned against the wall. Natural light streams through multiple windows, creating a bright and inviting atmosphere.

Home in Union Pier

House of Reilly - 5 Min Walk to Private Beach!

FamilyLocationHospitality

The exterior of the home features a charming design with a welcoming front porch and a peaked roof. Soft lighting highlights the entrance, surrounded by lush greenery and well-placed flower pots. The stone accents and wooden details contribute to a cozy cottage aesthetic.

5 out of 5 average rating, 98 reviews

Hot tub! Starlight cottage in Lakeside!

LocationFamilyIndoor spaces

4.96 out of 5 average rating, 136 reviews

Home in New Buffalo

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

LocationValueAir conditioning

5 out of 5 average rating, 13 reviews

Home in Union Pier

Peaceful 3Bed/2Ba, FirePit, Walk to Beach +Shops

LocationFamilyIndoor spaces

4.97 out of 5 average rating, 243 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

FamilyLocationLong stay

4.99 out of 5 average rating, 175 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

LocationFamilyBiking

4.98 out of 5 average rating, 100 reviews

The exterior of the barniminium is displayed, featuring a red and white color scheme. Windows are positioned symmetrically along the front, with a small seating area consisting of four white chairs and a table. The surrounding landscape includes grassy areas and subtle gravel pathways.

Home in Bridgman

The Schmidt House

LocationValueAccuracy

Other great vacation rentals in Lakeside

4.96 out of 5 average rating, 47 reviews

The exterior of Yellow Door Cottage is presented, featuring a charming dark blue facade with a bright yellow door. Surrounding greenery includes vibrant hydrangeas and lush ferns, contributing to a serene atmosphere. Large windows offer glimpses of the interior space.

Cabin in Lakeside

The Yellow Door Cottage

LocationFamilyComfort

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.

4.98 out of 5 average rating, 162 reviews

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

FamilyValueNearby

5 out of 5 average rating, 72 reviews

2-min Walk to Lake MI • Hot Tub + Sauna

LocationValueCondition

4.98 out of 5 average rating, 47 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!

ValueFamilyIndoor spaces

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.

4.96 out of 5 average rating, 282 reviews

Harbor Country Michigan Hide-Away

ValueFamilyNearby

4.99 out of 5 average rating, 280 reviews

A cozy sleeping area features a spacious bed adorned with neutral-toned blankets and decorative pillows. A large mural of outlined palm leaves decorates the wall above. Two pendant lights hang symmetrically on either side, providing soft illumination, and wooden nightstands are positioned on each side.

Bungalow in Sawyer

The Harbert Bungalow-Hot Tub-Walk to Beach

ValueFamilyLayout

4.88 out of 5 average rating, 17 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

LocationFamilyHospitality

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.