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Vacation rentals in Lakeside

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Top-rated vacation rentals in Lakeside

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
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.
Home in Lakeside

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

FamilyValueBeach

4.96 out of 5 average rating, 111 reviews
Guest favorite
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 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!

ValueLocationSolo travel

4.96 out of 5 average rating, 307 reviews
Guest favorite
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!

ValueLocationIndoor spaces

4.93 out of 5 average rating, 214 reviews
Luxe
An open entryway reveals a modern kitchen with a large island and four high stools. Natural light flows through multiple windows, highlighting the sleek countertops and rich cabinetry. A tasteful artwork adorns the wall beside the entrance, adding character to the space.
Home in Lakeside

Landmark Home 1 Blk from Lake MI Game Rm & EV Chgr

Sumptuous 4 BR/2.5 BA vacation home, just 1 block from Lake Michigan. Fully refurbished with reclaimed flooring, antique beams, custom doors, and fixtures. High-end kitchen, dining, and living areas with French windows. Living room features a stone fireplace, stylish couches, and a wide-screen TV. Three ground-floor bedrooms and baths with a second-floor bunk bed loft. Detached garage is a posh game room with high-end tables and a big TV. Covered patio, 4-seat dining, and bluestone courtyard.

ValueFamilyHeating

4.93 out of 5 average rating, 120 reviews
Guest favorite
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.

LocationFamilyBiking

4.91 out of 5 average rating, 140 reviews
Top guest favorite
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.
Cottage in Union Pier

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.

LocationFamilyPets

4.9 out of 5 average rating, 200 reviews
Top guest favorite
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.

LocationFamilyHiking

4.99 out of 5 average rating, 168 reviews
Top guest favorite
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.
Cottage in Union Pier

"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.

FamilyValueCondition

4.98 out of 5 average rating, 271 reviews
Top guest favorite
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.

LocationValueBeach

4.98 out of 5 average rating, 179 reviews
Top guest favorite
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.

ValueFamilyParks

5.0 out of 5 average rating, 153 reviews
Top guest favorite
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.
Cottage in Union Pier

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.

FamilyLocationLayout

4.98 out of 5 average rating, 166 reviews
Top guest favorite
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.
Home in Lakeside

Hot tub! Starlight cottage in Lakeside!

Feel relaxed, refreshed, & recharged! Our home is the perfect blend of comfort & cottage charm!Home is 2450 sq. ft., 3 bdrm,3 bth (2 BR, 2 BA in main home),updated & features a full kitchen, laundry room,6 TV’s,WiFi, & 2 eating areas.Attached guest apt. has 1 bdrm,1 bth upstairs w/ full kitchen,w/d,king bed, kids cubby w/ queen size gel mattress, & 2 TV’s.Guest apt. is attached & is perfect for people in your party requiring privacy!Close to everything in Harbor Country!

LocationFamilyOutdoor spaces

5.0 out of 5 average rating, 102 reviews

Popular amenities for Lakeside vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Lake side house rentals in Lakeside

Guest favorite
An indoor pool area features a bright, open design with vaulted wooden ceilings and intricate skylights. Surrounding the pool, large windows provide natural light, complemented by tiled flooring. Comfortable seating is positioned nearby, creating a relaxing and inviting atmosphere.
Home in Union Pier

Heated Indoor Pool & Tennis/Pickleball Court!

LocationFamilyIndoor spaces

4.85 out of 5 average rating, 108 reviews
Top guest favorite
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!

FamilyValueIndoor spaces

4.94 out of 5 average rating, 100 reviews
Superhost
The exterior of a two-story cabin is surrounded by lush greenery. Warm light filters through the windows, creating a welcoming ambiance. A stone pathway leads to the entrance, framed by natural landscaping and trees, inviting visitors to explore the serene setting.
Home in Chikaming Township

"Deer Crossing" Modern Cabin, Private Beach Access

ValueLocationAir conditioning

4.9 out of 5 average rating, 99 reviews
Top guest favorite
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!

LocationFamilyBeach

4.98 out of 5 average rating, 126 reviews
Superhost
A hot tub is situated on a patio, surrounded by lush greenery and outdoor furniture. A wooden deck is visible in the background, providing a relaxing atmosphere for outdoor gatherings. The sunlight reflects off the calm water surface, enhancing the serene environment.
Home in New Buffalo

Debs Michigan hot tub house, open all year

ValueLocationParks

4.85 out of 5 average rating, 622 reviews
Top guest favorite
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

FamilyLocationWifi

4.97 out of 5 average rating, 109 reviews
Guest favorite
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!

ValueFamilySleep quality

4.92 out of 5 average rating, 239 reviews
Top guest favorite
Home in Sawyer

Here and Now

LocationValueAccuracy

4.97 out of 5 average rating, 103 reviews

Other great vacation rentals in Lakeside

Top guest favorite
A cozy living area features a mix of modern and rustic decor, highlighted by large glass doors that open to scenic views. Warm wooden paneling surrounds comfortable leather seating and a coffee table, while large windows invite natural light into the space.
Guesthouse in New Buffalo

Rainbows End 🌈 Bourgeois

FamilyValueSolo travel

4.99 out of 5 average rating, 444 reviews
Top guest favorite
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.
Cottage in Union Pier

Harbor Country Michigan Hide-Away

FamilyValueAccuracy

4.97 out of 5 average rating, 291 reviews
Top guest favorite
Cottage in Union Pier

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

LocationFamilyComfort

5.0 out of 5 average rating, 75 reviews
Guest favorite
Home in Union Pier

Harbor Country Poolside

FamilyLocationAccuracy

5.0 out of 5 average rating, 21 reviews
Top guest favorite
Cabin in Lakeside

The Yellow Door Cottage

FamilyLocationDecor

4.96 out of 5 average rating, 53 reviews
Top guest favorite
A light-filled living area is characterized by high ceilings and large windows offering views of the outdoors. Soft beige furniture surrounds a round coffee table, while neutral tones create a calming environment. Decorative plants and art enhance the minimalist design, inviting relaxation.
Home in Union Pier

Designer home in Union Pier: steps to deeded beach

ValueFamilyLaundry

4.96 out of 5 average rating, 23 reviews
Guest favorite
Home in Lakeside

Charming Lakeside Bungalow

LocationFamilyKitchen

4.92 out of 5 average rating, 13 reviews
Guest favorite
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

4.89 out of 5 average rating, 19 reviews

All about Lakeside

Chicago residents have been escaping to the southeast coast of Lake Michigan for a century, and hidden among the tree-lined beaches of Lakeside are thousands of rustic cottages and inns. This is a retreat designed for relaxation: You can hike in the woods, swim, bike, go wine tasting, or just do nothing — many people are here specifically to soak up the sun and spend long afternoons reading amid the trees. Many shops, bars, and antique stores along Red Arrow Highway cater to urban tastes, and the mood is serene and friendly. (Lakeside is not an isolated getaway, however, and if you need to buy supplies, Michigan City, just over the Indiana border, is only 20 minutes away.)

What are the top things to do in Lakeside?

Warren Dunes State Park

Warren Dunes is kind of the Riviera of the southern coast, with miles of fine-sand beach that fills up with castle-builders and sun-seeking teenagers. If you hear excited screaming, look up to see kids who have climbed to the top of a 250-foot sand dune flying or rolling down.

Red Arrow Highway

This north-south road connects the towns of the southeastern Michigan coast, and the stretch from New Buffalo to Bridgeman is lined with galleries, craft stores, and antique shops selling both knickknacks and high-end furniture. You can also find welcoming cafes, roadhouses, and a beloved Turkish restaurant.

Three Oaks

The town of Three Oaks, just a few miles inland from Lakeside, is the center of the region’s biking culture. You can rent bikes from little cruisers to heavy-duty mountain bikes, and there’s a bike museum. Three Oaks has created 20 bike routes that range from short and flat to September’s Apple Cider Century bike tour of wine and orchard country.

Destinations to explore