Holiday rentals in Lakeside

5 out of 5 average rating, 199 reviews

Farm stay in Vandalia

One of a kind•HotTub•Fire Pit• Private•Lux•Charm

*Escape the ordinary and experience rural country luxury *Whether sipping coffee at sunrise or star gazing the Grain Binn is the perfect blend of rest and charm *Situated on 70 acres with flowing creek *Pickle Ball court 1 mile from Binn *Fully stocked kitchen *Fireplace *Hot tub with towels provided * Firepit with firewood *Bird feeder for Bird lovers *King size bed with quality bedding *Forgot something? Got cha *In floor heat *Snacks *Walking trails *Good WIFI *Unplug and un

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.

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.

4.88 out of 5 average rating, 125 reviews

Guest house in Sawyer

Lola's Pine Tree Cottage

Lola's Pine Tree Cottage is a uniquely perfect old-school Michigan Beach cottage, with modern amenities! Enjoy the quiet of 1.5 acre of combined yard and forest (with friendly deer and wills turkeys!); walk to the beach; snuggle in front of the fire! A perfect hideaway, fall, winter, spring, or summer! Close to all the charms and amenities of Sawyer, Three Oaks, Union Pier, New Buffalo, and St. Joes. Excellent writing retreat, we’ve been told, and a sweet spot for a romantic getaway!

Guest house 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

Flat 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, 229 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!

Guest house 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.

4.97 out of 5 average rating, 146 reviews

5 BR Cottage with Pier Street Beach Access

Wonderful classic cottage that has been updated with all the amenities that you would expect in a premium property. Centrally located to all that Harbor Country has to offer. Antiquing, wineries, art galleries, unique shopping and biking and hiking trails are minutes away.

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Popular amenities for Lakeside holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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.

4.97 out of 5 average rating, 75 reviews

The Honey Bee Lakeside

KatieRating, 5 stars2 weeks ago

This house was perfect for our impromptu weekend getaway! The space was clean & cozy. My friends and I felt right at home. Perfect location for all your Union Pier, Lakeside and Harbert needs!

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, 32 reviews

Cozy Lake House with Bonus Guest Cottage!

SarahRating, 5 stars9 months ago

Sandy's house was very comfortable and cute. The house has many different places places to hang out (living room, porch, fire pit area, and patio area). Each area is very peaceful. Our group had such a great time hanging out there and it was about 2-3 blocks walk to the beach. Sandy had flowers from her garden in vases for us and made us feel like we were home. We would definitely stay at Sandy's again!

4.89 out of 5 average rating, 44 reviews

Contemporary Romantic Cottage - 2 Blks. to Sunset

ShyaneRating, 5 stars9 months ago

The house was so comfortable and inviting from cooking a meal in the open kitchen to sitting on the screened in porch just relaxing. Within walking distance to the beach and cute little cafés close by. Perfect location to visit all the other towns along the water. The host was very friendly and the beds very comfortable! We will definitely be back!

5 out of 5 average rating, 22 reviews

Guest house in Sawyer

Flynn Coach House

AnnRating, 5 stars8 months ago

Denise &Ninel are wonderful! One of the best experiences we've had. The property is stunning and so peaceful. We enjoyed the spacious deck and walks in the woods. Pristine accommodations that were very comfortable for our party of 5. We loved being able to spend time together cooking in the well equipped kitchen, while doing puzzles and crafts at the large table. The gas fireplace and comfortable seating were perfect for latenight movies as well. The property is a great base for exploring Harbor Country, only minutes away from the beach, great restaurants, wineries, and all SW Michigan has to offer. Will definitely stay again!

4.97 out of 5 average rating, 33 reviews

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.

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