Vacation rentals in Lakeside

4.95 out of 5 average rating, 366 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, 193 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, 155 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, 248 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, 140 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, 377 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, 336 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, 278 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!

A two-story, light green cabin is set among lush greenery, with a well-maintained lawn and flower beds. Steps lead to the entrance, framed by decorative windows. Lake Michigan is visible in the background, surrounded by trees and an inviting blue sky.