
Vacation rentals in Lakeside
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Popular amenities for Lakeside vacation rentals
Lakeside house rentals

Pet friendly stylish retreat with sauna, hot tub

The Heartwood House<3 : DT Three Oaks w/Game Room

Private Beach/Lake Michigan/Panoramic View/Hot Tub

Cozy Vintage Cottage Near the Lake

Casa Gitana - Boutique Style Stay in Three Oaks

The Walnut House, Michigan Woods Retreat

Wandering Soul Cabin

Family Getaway with Year Round Hot Tub!
Lakeside cottage rentals

Beach Bird Cottage- 5min walk to the lake! 3BR/1BA

The Pines Cottage on Birchwood

Casa Playa New House in Union Pier w/ Private Spa

Lake Bluff cottage, Unforgettable view and sunsets

New Buffalo retreat - Perfect year-round getaway!

Designer Cottage Relax Beach Pool & Spa—Windjammer

Prime Summer Days Still Open @ Birchwood Cottage!

Camp Wanderlust-Cozy lodge-20 minute walk to beach
Lakeside fishing vacation rentals

The Bright Yellow Retreat

Splash (Pool! Hot Tub!) at Aqua House by the Lake

Cozy Green Cottage with Private Beach

Lake House Retreat with a Pool

Pure Michiana - Rustic & Cozy - near the stateline

Pet friendly, lakefront home w/kayaks & pontoon!

Beach! Hot Tub! New Buffalo! Firepit! King Bed!

Quiet Grand Mere Coach House on Lake Michigan
Your guide to Lakeside
Introduction
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.)
The best time to stay in a vacation rental in Lakeside
If you prefer gentle climates, May through September are definitely the best months to visit the southern Lake Michigan coast. The lake tempers the heat during the summer, but temperatures in the 80s Fahrenheit are still common. As July segues into August the humidity goes up — you’ll want to make frequent trips to the lake to cool down. (Essential protections: sunglasses, sunblock, and bug spray.)
Autumn, which begins in mid-September, is a magnificent time to stay in one of the area’s cottage rentals, with crisp air and brilliantly colored foliage. Winters stretch from early December to the beginning of March. During those months, temperatures below the 40s Fahrenheit are the norm, and the lakeshore effect brings freezing winds and snows to much of southern Michigan and northern Indiana.
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.
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- Millennium Park
- Navy Pier
- Warren Dunes State Park
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- University of Notre Dame
- Lincoln Park
- Museum of Science and Industry
- Washington Park Zoo
- Lincoln Park Zoo
- Willis Tower
- Potato Creek State Park
- Silver Beach Carousel
- Chicago Cultural Center
- Adler Planetarium
- DuSable Museum of African American History
- Chicago History Museum
- Culver Academies Golf Course
- Promontory Point
- Buckingham Fountain
- Deep River Waterpark
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