Holiday houses in Lakeside

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Top-rated holiday rentals in Lakeside

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

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Guest favourite

Farm stay in La Porte

4.99 out of 5 average rating, 441 reviews

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.

2 – 9 Aug

$1,722 AUD total

Guest favourite

Home in Lakeside

4.96 out of 5 average rating, 157 reviews

Adorable couples escape with year-round hot tub!

3 NIGHT MIN JUNE 15 - END OF AUG! 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!

7 – 14 Mar

$2,982 AUD total

Guest favourite

Apartment in Sawyer

4.97 out of 5 average rating, 270 reviews

Ozzie’s Hideaway-Smack between Three Oaks & Sawyer

This entirely redone, adorable apartment features automotive themed collectibles and vintage finds, black & white photos, car part art & furniture. Custom made pillowcases and duvet covers portray the ultimate road trip. Play the license plate game you played riding in the backseat as a kid, with our collection of license plates. The boomerang countertops welcome you in a fully equipped kitchen, an outdoor patio, grill and fire pit will help you create lasting memories of your next road trip.

17 – 24 May

$1,529 AUD total

Guest favourite

Home in Lakeside

4.99 out of 5 average rating, 101 reviews

Lakeside Retreat Nestled Among the Trees

Welcome to our cozy 'Tree House,' nestled among the trees in Lakeside, Michigan! Our renovated cottage is located 90 minutes from Chicago in the heart of all that Harbor Country has to offer. Our bright, open home features high end finishes, luxury mattresses and comfortable seating. Nature-inspired hues invite you in, making relaxation a top priority! Generous outdoor spaces include a large deck with ample dining space, rocking chairs, and two outdoor fire pits for s'mores under the stars.

22 – 29 Oct

$4,959 AUD total

Guest favourite

Cottage in Union Pier

4.97 out of 5 average rating, 185 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. Newly updated cabin-style home offers rustic feel with luxury comforts & highspeed WiFi, and great indoor & outdoor space. Garage plus add'l 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.

8 – 15 Dec

$2,524 AUD total

Guest favourite

Guesthouse in New Buffalo

4.98 out of 5 average rating, 695 reviews

"Tiny House" Guest House Under the Oak Trees

"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 a grill. Convenient charger for electric cars. Never a cleaning fee.

21 – 28 May

$1,532 AUD total

Guest favourite

Cabin in Union Pier

4.96 out of 5 average rating, 292 reviews

McComb's Cabin, Union Pier, MI

Giant trees welcome you down the drive back to the secluded cabin in the woods. 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/ birthdays - Singles, seeking a simple life under the pines.

24 Nov – 1 Dec

$1,858 AUD total

Guest favourite

Cottage in Union Pier

4.95 out of 5 average rating, 272 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!

25 Sept – 2 Oct

$3,938 AUD total

Guest favourite

Guesthouse in New Buffalo

4.96 out of 5 average rating, 471 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!

6 – 13 Mar

$1,723 AUD total

Guest favourite

Guesthouse in Sawyer

4.92 out of 5 average rating, 150 reviews

Heron's Rest hideaway close to beaches, breweries

Privacy on 11 acres of conservancy-protected land including woods, two ponds, and a river. Minutes from Michigan’s most popular beach, breweries, wineries, antique malls, farm-to-table restaurants. Fully equipped kitchen, gas fireplace. Private fire pit, deck, and gas grill. Fish on site. Kayak, bike, hike nearby. Ideal for nature lovers. Separated from our home by breezeway. Private entrance, quiet road, dark nights. Daytime woodworking noise possible.

2 – 9 May

$1,327 AUD total

Guest favourite

Cottage in Sawyer

4.93 out of 5 average rating, 208 reviews

Northwind Llama retreat “Chicken coop”

Enjoy your farm style experience- Llamas, chicken’s, dog’s and cats! 400 sq. ft. "Efficiency Suite" Revel and Relax . Rest in the queen memory foam bed complete with custom Upstate bedding. The open space living area has ample seating, desk, and full- size fridge for your libation. Private bathroom with stand up shower with exclusive Robert Jeffrey products. Your family pet is welcome! Please add your pet to rsvp !

17 – 24 Nov

$1,680 AUD total

Guest favourite

Cottage in Union Pier

4.98 out of 5 average rating, 148 reviews

Union Pier Cottage—Steps to lake, hot tub, sauna!

Charming modern vintage cottage located steps away from the beach! Sleeps 6 guests with 2 queen beds, 1 king bed, 1.5 bathrooms + a fully private, hot/cold outdoor shower! Huge fenced-in backyard! Washer/dryer. Eat-in kitchen. Heat, A/C. Front & back decks with outdoor seating, fire pit, grill, sauna, hot tub, beach chairs, cooler, and towels. Includes up to 5 parking spots with a 240V outlet for charging.

24 – 31 Jan

$5,310 AUD total