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 !!

1920s fully updated unique open artist loft space

True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

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)

Modern, Open, Logan Square Loft w/ Unique Design

Welcome to our open concept studio loft. Located in the heart of Logan Square, we are walking distance to Palmer Square Park, plus some of the cities best coffee shops, restaurants, galleries and summer festivals. This space is airy, naturally lit, and comfortable with a 15' floor to ceiling main atrium, full height windows and custom architectural light screen plus all the amenities to make your stay comfortable. Easy access to public transportation makes getting around the city a breeze

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.

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

Historic Arts District Gastro Loft

This newly renovated loft was re-created from a long-neglected space in the historic Sheffield building. A perfect getaway for two, the loft is located above the area’s hottest new restaurant, the Houndstooth. Classic urban finishes - high ceilings, exposed brick, hardwood floors...and an expansive view of City Center Park.  Houndstooth draws diners from as far away as Chicago - a visit to Benton Harbor will not be complete without experiencing the big city fare of this hot spot.

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.