Holiday houses in Lakeside

4.95 out of 5 average rating, 335 reviews

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.

Superhost

Home in Union Pier

4.91 out of 5 average rating, 221 reviews

CASA TICA Serenity Amongst Nature Dog Friendly

Come spend your holiday retreat in truely private loft house. Casa Tica has the feel of tree house surrounded by trees, living space on 2nd floor on acre of moss tree lined trails. Sit on your lrg 10x14 deck and listen to the birds sing and gaze from above into the beautiful woods. This is your space to feel alone and amongst nature. Behind your loft look out to the magical woods and enjoy a fire at the bomb fire pit or let the kid loose in you and swing on the architectural swing set.

4.93 out of 5 average rating, 114 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.

4.9 out of 5 average rating, 153 reviews

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.

4.99 out of 5 average rating, 131 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.

5 out of 5 average rating, 126 reviews

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.

Guesthouse in New Buffalo

4.98 out of 5 average rating, 838 reviews

"Tiny House" Guest House - No Cleaning Fee

"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.

4.93 out of 5 average rating, 344 reviews

Cottage in Union Pier

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!

4.88 out of 5 average rating, 104 reviews

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 local beers, seltzer water and a snack are provided to help kick off your stay.

4.96 out of 5 average rating, 230 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!

4.98 out of 5 average rating, 407 reviews

Farm stay in Sawyer

Your SW Michigan Modern Farmhouse Cottage Awaits

Located in Sawyer, you can bike or drive to countless beaches, breweries, wineries, distilleries, and outdoor adventures. Afterward come home to this stylish modern farmhouse cottage that looks out onto 14 acres of scenic barn, pasture. and woods. Your home away from home has a well appointed kitchen for foodies who like to cook or great local dining options for those who don't.

Guesthouse in New Buffalo

4.99 out of 5 average rating, 353 reviews

Rainbows End 🌈 Bourgeois

Escape to a pet-friendly cottage in the Midwest. Nestled amidst scenic trails, with access to the South Branch of Galien River. Relax in the whirlpool tub, explore nature, and create cherished memories. Fully equipped kitchen, washer/dryer, and inviting ambiance. 10 mins from Lake Michigan, 3 miles from Fourwinds Casino. Experience rural bliss in this delightful cottage.

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Other great holiday rentals in Lakeside

4.67 out of 5 average rating, 6 reviews

2BR garden-style cottage with beach access

GintareRating, 5 stars9 months ago

We had a lovely stay at this cottage. It’s exactly what you would expect from a “garden-style” cottage in the area. The beach was, without a doubt, the highlight of our stay. It was amazing, clean, close, easy to access, and had plenty of space to spread out and relax. The kitchen had the basics of what we needed. Overall, we had a nice, peaceful weekend.

4.99 out of 5 average rating, 95 reviews

Cabin in Union Pier

Walk 2 Lake/Shops | Hot Tub | King Bed | Fireplace

IonitRating, 5 stars2 days ago

Thank you for hosting, Sarah! We enjoyed walking to the beach and crossing the street for coffee and pastries at the Blackcurrent Bakery.

4.88 out of 5 average rating, 72 reviews

Cottage in Lakeside

Kelly Kottage

AnneRating, 5 stars9 months ago

We had a great time at Candi’s cabin. Everything was very nice and clean. The fire pit was perfect for s’mores and we particularly enjoyed the screen porch.

4.63 out of 5 average rating, 16 reviews

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

VictoriaRating, 5 stars8 months ago

The house was great: super clean, great beach access, and comfortable for two couples. My only tip: There are no window coverings on the bedroom windows, so depending on the time of year the sunlight may wake you earlier than you would like.

4.97 out of 5 average rating, 33 reviews

Cottage in Lakeside

Lakeside House w/ Private Beach Access

MichelleRating, 5 stars9 months ago

This is our second time staying here this summer. We enjoyed it so much the first time we booked again. Great location with tons of good local eats. Christen is very easy to work with and so communicative. The house feels like home- so much that our kids asked when we were moving here. The walk to the beach is short and the privacy of the beach is so nice.

5 out of 5 average rating, 96 reviews

Home in La Porte

UncleLarrysLakePlace HotTubKayaksPingPong

Sai SharukRating, 5 stars1 week ago

An amazing place to stay for our group’s senior trip. The view and surrounding area was peaceful yet vibrant. The AirBnB was beautiful, having several useful amenities plus being very clean upon our stay. Jamie is an amazing host and was very responsive to our needs!