Holiday rentals in Lakeside

5 out of 5 average rating, 201 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.

4.92 out of 5 average rating, 115 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.

4.99 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.

Guest house in New Buffalo

4.98 out of 5 average rating, 840 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, 345 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, 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!

Guest house in New Buffalo

4.97 out of 5 average rating, 593 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!

4.94 out of 5 average rating, 512 reviews

Flat in Sawyer

Cozy Chalet by Lake MI&Dunes with Fire Pit

Sawyer Gem: Cozy Vintage Retreat Near Lake & Dunes! Charming vintage chalet sleeps 4 . Sun-drenched sunroom, private fire pit. Walk to restaurants, bars, antiques. Minutes to Lake Michigan & Warren Dunes. Adding to its unique charm, The Cozy Chalet is directly connected to Harbor Country Mission, a wonderful antique shop supporting the local community. You'll enjoy a separate entrance for complete privacy and convenience. Book your stay today!

4.98 out of 5 average rating, 151 reviews

Home in Sawyer

Wandering Soul Cabin

Wandering Soul Cabin is a contemporary country farmhouse harmoniously nestled within its natural surroundings, only minutes away from Downtown Sawyer and Cherry Beach. This inviting cabin has three bedrooms and two and a half baths. The primary suite features a king-sized bed, French doors that open onto a deck overlooking the backyard, with a path right to the pond, canoe and community garden.

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Popular amenities for Lakeside holiday rentals

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Air conditioning

Other great holiday rentals in Lakeside

Serviced apartment in New Buffalo

4.92 out of 5 average rating, 36 reviews

Charming 1BR/1BA Retreat with private beach access

AtaRating, 5 stars6 days ago

It was an excellent time staying in this property. Everything was great and we will definitely want to go back. Check in was easy. Managers were so helpful and friendly specially Pamela. Loved the fire-pits outside. Excellent location and very close to a beautiful private beach, local stores and restaurants.

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!

4.86 out of 5 average rating, 73 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.

5 out of 5 average rating, 23 reviews

Cottage in Union Pier

Charming Cottage - Hot Tub, Sauna, Large Yard

CarinaRating, 5 stars1 week ago

We loved our stay at Ashley and Bobby’s! The yard was great for our dogs and the beach, sauna and hot tub were great for us. Perfect spot for a peaceful week away. Bobby and Ashley were extremely accommodating and responsive to any needs. They have a beautiful home and I hope we can return!!

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!

5 out of 5 average rating, 21 reviews

Private! Warren Woods Pool Retreat

OliviaRating, 5 stars5 months ago

Staying at Mary’s place was wonderful! It had everything we needed for the holidays and she was easily available for any questions. Only a 5 minute drive into town! I would definitely stay here again.