Book a Chic Stay

By Kristine Hansen | Photography by Dave Burk, Kinn Guesthouse

Pairing a cool boutique hotel stay with browsing at nearby shops and enjoying winter-wonderland activities is the perfect way to pamper yourself during the long winter months. Make it a family adventure or grab just the gals for a grand time as a group.

From Milwaukee’s bustling downtown to a luxury staycation right here in town, these boutique hotels check all the boxes — they’re oozing with style, are right here in Madison or under two hours away, and are near attractions and activities.


In the heart of downtown, the 219-room Saint Kate Arts Hotel is loaded with art, such as artist- made touches in the rooms (from lampshades to the Kohler-branded sinks) and large-scale art installations in the lobby. The hotel even serves as a satellite location for West Bend’s Museum of Wisconsin Art, accessible from the lobby.

Clink flutes of bubbly at champagne bar Giggly, kick back in your room with pizzas from Proof Pizza or dress up for surf-and-turf dinner at Aria.

Also check out: Ice skating at nearby Red Arrow Park or the bars and restaurants in the Deer District outside Fiserv Forum.


Want to spread out with your group or have an Airbnb-type experience? These two connected historic 1898 buildings on the city’s East Side were once home to siblings and their families. The property’s décor details include Persian area rugs, hardwood floors and individual climate controls in its 17 rooms. Gülden Room’s salon-style coffee bar downstairs means you never have to go without a crafted cup in-hand.

Also check out: Instagram-worthy coffee and espresso drinks at Milwaukee Art Museum’s Discourse Coffee: Coffee Workshop or grab a brew at quintessential pub The Swingin’ Door Exchange. The wood bar and old-timey beer signs scream classic Milwaukee.


High on a hill, this 38-room hotel in charming Delafield features in-room massages, a fine-dining restaurant (I.d.) and a partnership with the gym next door. Lining the downtown streets are boutiques and cafes, including Blue Collar Coffee Co. for your pumpkin-spice latte fix. Fun fact: Delafield’s Colonial-style downtown was developed by Robert Lang, who founded the picturesque-scene stationary and calendar line, LANG.

Also check out: Dine in an igloo or inside Belfrē Kitchen (a former church) or cross-country ski at nearby Lapham Peak.


The city-chic hotel located in the former Mautz Paint Co. factory is ripe for a staycation with its pet-friendly vibe and you’ve-earned-this steaks at Palette Bar & Grill. Treat yourself to a night out — without the drive back home or trying to find parking — with artfully-prepared dishes at A Pig in a Fur Coat or cocktails at Old Sugar Distillery, both within a short walk.

Gift yourself with an item from nearby Hazel General Store, such as a candle or bath and body product.

Also check out: Ice skating at Tenney Park or sip a brew at PROST! Beer Hall.


Hearken back to college days — but with more class — via the plaid-motif- meets-Northwoods décor at this 72-room, pet-friendly hotel wedged between State and Langdon streets. Camp Trippalindee sports amazing views of the State Capitol from its rooftop perch and serves up deep-fried cheese curds while the lobby-level Poindexter Coffee’s breakfast sandwiches are worth coming back for after the staycation’s over.

Also check out: Stroll on State Street and enjoy the downtown views or grab a from-scratch bakery item and a seasonal hot drink at Colectivo Coffee.


On the banks of the Rock River, this 54-room hotel welcomes dogs — and even gifts them with a ball, treat and hotel-branded bandana. Rooms are spacious and flaunt luxe features like rainfall showers and plush robes. Ring the front desk in advance, and truffles and sparkling wine will be waiting in your room.

Also check out: Browse the Wright Museum of Art’s 6,000 works of art or pick up gourmet food gifts at Bushel & Peck’s.


Now with two locations, this eight-room Bay View property opened in 2017, and was followed by a 31-room downtown Milwaukee sibling earlier this year. The vibe is like checking into your cool cousin’s place, with eclectic décor and communal kitchens on every floor. Don’t want to cook? Sorella is on-site at the Bay View location, while the Wolf of Broadway is opening soon in the downtown hotel. Also near the downtown hotel: the Milwaukee Public Market (akin to Seattle’s Pike Place Market) for a cool culinary experience.

Also check out: Indie boutiques in Bay View, URSA; and downtown, (MOD GEN). Sip a seasonal hot drink at Hi-Fi Cafe (Bayview) or book an afternoon tea service at the Pfister Hotel downtown.


The crown jewel at this 34-room hotel is the rooftop. And because it’s enclosed in glass, it doesn’t close during winter! Grab cocktails and snackboards with a view (and cozy up by the firepits) before sitting down to an Italian menu at Velvet Buffalo inside the hotel.

Also check out: Take a stroll through Big Hill Park, known for its scenic views and bird-watching. At night head to 5BAR, a midcentury modern-chic bar with a cool vibe.

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