Vacation rentals in Lakeside
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Top-rated vacation rentals in Lakeside
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Couples alert! PVT beach access, hot tub, firepit!
ADORABLE LAKESIDE COTTAGE W/YEAR-ROUND HOT TUB AND A GUEST FAVORITE - ACCESS TO SEMI-PRIVATE LAKE MICHIGAN BEACH SHARED BY JUST 10 HOMES SO IT'S NEVER CROWDED! BEACH ACCESS GATE IS 7 MIN WALK FROM COTTAGE. LOFT LIKE HOME IS SUPER CLEAN WITH VERY COMFY KING SIZE BED AND ONE PULL-OUT COUCH FOR 4 GUEST (MAX). FIREPIT SUPPLIED WITH WOOD, AN OUTDOOR PATIO AND WEBER GRILL - YOU WILL LOVE IT! Bike/walking path out front and just 10 mins to New Buffalo, Whistle Stop, coffee - just steps away!! HURRY!
The Honey Bee Lakeside
Keep it simple at this peaceful, centrally-located place. Modern and pristinely cared for home w/open floor plan offers privacy and autonomy. Close to Harbor Country beaches and amenities. Set on an acre with gorgeous screen porch to while away the afternoons, plus large deck built around a giant oak to commune with nature, and fire pit to hang with friends. Attached garage with ping pong for the youngsters and young at heart. En suite primary plus two additional bedrooms. 6 adults, 2 dogs max
Cozy Green Cottage with Private Beach
Cozy cottage hidden away in a quiet neighborhood 1.5 blocks from Lake Michigan, featuring a screened back porch perfect for morning coffee. Near the Benton Harbor Arts District, downtown St Joe, this cottage is surrounded by local restaurants, breweries, wineries, golf courses and shops. The beach is a year round destination, each season has its own wonders. Note: no TV, and WiFi can be spotty due to hills. Expect 90+ tiered steps to the sandy beach below. AC upstairs, original claw footed tub.
Charming Harbor Country Chalet with Hot Tub
Excited to share our home with you! Handcrafted in the 80’s from the hardwoods grown on the property, our home was built by the original owners to resemble a Swiss Chalet. There are 3 bedrooms, 2 baths and a kitchen with a breakfast bar and dining table for 6. The house has cathedral ceilings and plenty of natural light. Ideal for a small family or a group of friends. There is a fire pit in our large backyard and a hot tub and gas grill on the wraparound porch. Instagram @harborcountrychalet
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!
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.
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.
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.
"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.
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.
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.
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.
Popular amenities for Lakeside vacation rentals
Lake side house rentals in Lakeside
House of Reilly - 5 Min Walk to Private Beach!
The Walnut House, Michigan Woods Retreat
Barn & Beach Guest house New Buffalo/Union Pier
Private Beach/Hot Tub/Sauna/Lake Michigan
Steps to Beach & Starbucks! Private Yard, Firepit!
The Schmidt House
Here and Now
Aunt Betty's Lakeside Abode, Hot Tub Steam Shower
Other great vacation rentals in Lakeside
Designer Cottage Relax Pool Beach & Spa—Windjammer
Family Getaway with Year Round Hot Tub!
CASA TICA Serenity Amongst Nature Dog Friendly
McComb's Cabin, Union Pier, MI
The Cranny at Michaels Nook
The Cottage of Harbor Country - Close to it all!
TRYON FARM MID-MODERN SPA IN THE WOODS
The Yellow Door Cottage
All about Lakeside
Chicago residents have been escaping to the southeast coast of Lake Michigan for a century, and hidden among the tree-lined beaches of Lakeside are thousands of rustic cottages and inns. This is a retreat designed for relaxation: You can hike in the woods, swim, bike, go wine tasting, or just do nothing — many people are here specifically to soak up the sun and spend long afternoons reading amid the trees. Many shops, bars, and antique stores along Red Arrow Highway cater to urban tastes, and the mood is serene and friendly. (Lakeside is not an isolated getaway, however, and if you need to buy supplies, Michigan City, just over the Indiana border, is only 20 minutes away.)
What are the top things to do in Lakeside?
Warren Dunes State Park
Warren Dunes is kind of the Riviera of the southern coast, with miles of fine-sand beach that fills up with castle-builders and sun-seeking teenagers. If you hear excited screaming, look up to see kids who have climbed to the top of a 250-foot sand dune flying or rolling down.
Red Arrow Highway
This north-south road connects the towns of the southeastern Michigan coast, and the stretch from New Buffalo to Bridgeman is lined with galleries, craft stores, and antique shops selling both knickknacks and high-end furniture. You can also find welcoming cafes, roadhouses, and a beloved Turkish restaurant.
Three Oaks
The town of Three Oaks, just a few miles inland from Lakeside, is the center of the region’s biking culture. You can rent bikes from little cruisers to heavy-duty mountain bikes, and there’s a bike museum. Three Oaks has created 20 bike routes that range from short and flat to September’s Apple Cider Century bike tour of wine and orchard country.
Destinations to explore
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- Soldier Field
- Lincoln Park
- Grant Park
- Warren Dunes State Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- 875 North Michigan Avenue
- University of Notre Dame
- University of Chicago
- The Field Museum
- Shedd Aquarium
- Guaranteed Rate Field
- Lincoln Park Zoo
- Beachwalk Vacation Rentals
- Washington Park Zoo
- Oak Street Beach
- Museum of Science and Industry
- Chicago Theatre
- Silver Beach Carousel
- Potato Creek State Park
- Wintrust Arena
- Chicago History Museum
- New Buffalo Public Beach