Shorewood is one of the most revived neighborhoods in Milwaukee, so it’s no surprise that this loft is hip, trendy, and very happening. The loft is within walking distance of cool, chic bars as well as awesome shopping and restaurants. More importantly, it’s only a minutes-long trek to the beach of Lake Michigan. This place is perfect for those couples or families looking to have a bit of a quieter, nature-filled trip away from the hustle and bustle of downtown. That being said, downtown is only a 10-minute drive. Major plusses include an attentive but respectful host, Lynne, a very friendly 13-year-old dog, papillon/poodle mix that likes everyone, and croissants any time before 9am!
Cost Per Night: $95
If you’ve ever dreamed of a life at sea, then look no further than the beautiful waters of Lake Michigan! This 32′ yacht (yes yacht) is perfectly equipped for a wonderful escape to southern Wisconsin. The marina is ideal for walking around or taking a quick bike ride, and the best part is that some restaurants will actually deliver to the boat! So enjoy a meal in the galley or up on the deck for a perfect Milwaukee night.
Cost Per Night: $125
This location is perfect for a group of vagabond friends traveling the world and looking for the coolest places and best experiences! This house is on both the national and historical registry and was originally built as a single standing house for Milwaukee fixture, Sanford Kane. The house is composed of “Cream City” brick, which are the inspiration behind the city’s nickname of “Cream City.” This artsy abode is a fantastically whimsical place to spend a weekend in Milwaukee.
Riverwest is the ‘humble-brag’ of the city of Milwaukee. It’s cool, it’s effortless, and it’s filled with people who are amazing and eclectic. There are fantastic trails, restaurants and shopping just a stone’s throw away from this fabulous private guest house. It has recently been renovated, and it shows in its enticing details throughout. This cozy and fun place is a fabulous family or couple home to stay in all year round.
The Hawk’s Nest is the name of a fabulous building that will transport any guest from the bustling city to a country feel in seconds. Despite the fact of feeling like Anne of Green Gables, the Hawk’s Nest is only a small distance from most of the Milwaukee hubbub. Speaking of literary characters, the room offered gives up massive “Chronicles of Narnia” vibes, as the entrance is literally a secret bookshelf! They are close to the river and have an inflatable kayak for those wanting to venture out. What more could you need?
This suite is perfect for long lost reunions of college friends or just a laidback romantic weekend. Check out that awesome bathroom! It is near to many restaurants, bars, and clubs… and has its own private entrance. The owners are all about making the stay a positive event, so that everyone can love Milwaukee as much as they do.
Cost Per Night: $81
Solo adventurers and business travelers get ready, this place is fantastic for Instagram or chill nights preparing for an important presentation. Seven minutes south of downtown, this place is close to everything. Restaurants, bars, whatever you may need, including a quick trek to Lake Michigan. There’s laundry access, and a full kitchen, so at this point just book it out for a few weeks and get to know the city!
New York has the Ninja Turtle lair, Georgia has this killer tree house, and Milwaukee has the Captain’s Quarters. This exciting abode is completely ‘decked’ out from head to toe in the coolest tiki gear you’ve ever seen. Hawaii has come to Milwaukee in this totally awesome home above the “Foundation Tiki Bar” which was rated #4 on Critiki’s Ten Best Tiki Bars in the World 2016. So grab a Pina Colada and cool off… unless it’s winter, in which case – stay warm!
Ever wanted to be walking distance from all of the best places in Milwaukee? Then be sure to book this historic mansion room, which is so close to the lakefront, Art Museum, Summerfest, all of the best neighborhoods within the city. This means access to the coolest restaurants, and of course, the best views in the city.
If the hipster lifestyle is one that has always enticed you, then live your best Milwaukee life by staying in this picture perfect apartment. This place is decked out in all of the most adorable decor – making it irresistible to those staying there. Be sure to take a lot of pictures and take some style notes for your own unique abode. This place is also near some awesome taprooms, so get ready for a craft beer extravaganza!