Loft vacation rentals in Lake Michigan

Windy City Suite At The Stewart

Enjoy the best view of the Arts District perched high above the streets below with 180 degree views from the bay windows. Sleep in tranquility in the soft king size bed in the master bedroom. Cook a classic continental breakfast of scrambled eggs, bacon or waffles (provided) or grab one of the best breakfasts around at Mason Jar or coffee at Forte Coffee! Walk to The Livery, Houndstooth Restaurant, Larks BBQ, Pipestone Indoor Golf or Harbor Shores Golf Course too! Industrial, elegant, romantic.

Downtown Traverse City Loft in Historic Firehouse

Firehouse One is a landmark historic building in the heart of Downtown Traverse City, just steps from West Bay, fine dining, and boutique shopping. Built in 1891 as the city’s first fire station, it was fully restored in 2025 to combine timeless charm with modern luxury. This loft showcases soaring 15’ ceilings, open air walls with three stylish bedrooms, a full bathroom, and a newly designed chef’s kitchen—designed to create an elegant, comfortable, and unforgettable stay. +2 parking spots !!

[Hidden Gem] steps to Short’s +restaurants + shops

Turn of the century home located in Downtown Bellaire. The second story has been converted into a private flat, with the famous Flying Pig store located in the retail space below. Just steps away from Short's Brewing Company, Mammoth Distilling, and downtown district of Bellaire. Just a short drive to Torch Lake, Shanty Creek Resort, Glacial Hills Trails, Lake Bellaire, and all of the surrounding chain of lakes and rivers. *If you are bringing a pet, you must add it to your reservation*

Romantic Gastro Loft Retreat for Two

Located above the area’s hottest new restaurant, this newly renovated 1BR/1BA urban loft features classic finishes - exposed brick, high ceilings, maple floors, and quartz countertops. Cozy, comfortable quarters directly above the Houndstooth restaurant provide a fantastic opportunity to get a “taste” of the Benton Harbor Arts District. Muffled sounds of music and activity from the restaurant below are often present in the loft during evening hours. Some guests may find this objectionable.

Wicker Park Loft - Walk To Everything!

Walk to Bucktown & Wicker Park bars, restaurants & shopping from this large apartment in working artists' building. 10 minute WALK to CTA Blue line TRAIN. FREE STREET PARKING. Premium mattresses and all essentials provided. Resident artists work on the first floor of this historic former telephone repair and switching station. Very laid back vibe. NOTE All guests must be on your reservation for an accurate $total. There is a $30 per night/ per guest charge AFTER 2 Guests (3rd to 5th)

Pilsen Modernist, Creative, Lightfilled Loft

Take morning drinks through the sunshine-yellow room to the back porch, or watch light dance on translucent walls and glossy black and white hardwood floors. Eclectic design includes a mix of new and vintage furniture, and a collection of art and design books for guests to enjoy. This unit is owned by an artist couple who split their time between Tucson, AZ and Chicago. This is their personal unit when they're in Chicago. Come stay here to get away, be comfortable, relax, and be inspired.

Fantastic Downtown Loft

Unique beautiful downtown loft overlooking 8th street shops and restaurants. Incredible space with 2 master bedrooms plus twin bed studio area. Full kitchen, dining area, seating areas, TV/ bar room, fireplace, library, and private roof top deck with hot tub and grill complete this one-of-a-kind home. Two reserved parking spaces. 100% updated. The building dates to the 1890's and all the brick and flooring is original, but everything else is new while the character has been preserved.

The Candy Loft in Arts District - 1BR/1.5BA Luxury

Welcome to The Candy Loft in Benton Harbor's Arts District! This 1BR/1.5BA condo boasts exposed brick, a king bed, and an oversized river rock shower in a spa-like bathroom illuminated by a skylight. The chef’s kitchen features a luxe Kitchenaid gas range, and an air mattress adds extra sleeping space. Housed in a historic candy factory, with an office in a former elevator shaft, it’s walking distance to restaurants, a brewery, and a coffee shop. Note: on the 2nd floor, stairs required.

Cozy Carriage House Loft – Walk to Lake & Downtown

Relax in this cozy Carriage House Loft, tucked in the heart of historic Port Washington. Just a mile from Lake Michigan, sandy beaches, the iconic lighthouse, marina, and the charming downtown with local dining, coffee shops, and boutique shopping. This private retreat has its own entrance and is set in a quiet neighborhood, giving you the ideal mix of seclusion and accessibility. You’re only a 30-minute drive to downtown Milwaukee, and a scenic 30 miles south of Sheboygan and Kohler.

Cute Urban Loft Gem: Minutes to Downtown & Beaches

Soak up summer in this stylish, highly rated downtown Traverse City loft—one of the area’s highest rated stays! "Cute & Cozy" offers 550 sq. ft. of charm with a plush king bed, queen sleeper, full kitchen, and big-screen TV. Ideal for couples or small families. Walk to beaches, bars, top restaurants, festivals, and shops! Sip wine, enjoy snacks, and relax. Guests love the comfort, quiet vibe, and unbeatable location. 5-star reviews, fast Wi-Fi, and free parking—book your stay now!

Hidden Country Hide-A-Way

Come relax in our cozy, modern country, studio apartment. It is  equipt with a fully stocked kitchenette, private bathroom, comfortable living space, large screen tv and office work space.  Enjoy some of the most picturesque landscape Northern Indiana has to offer.  We are just a 10 min walk from Stone Lake and have kayak rentals available upon request.  We are conveniently located 8 miles from Shipshewana and Middlebury, IN and just a 40 minute drive from Notre Dame.

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.