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Milwaukee is having a moment. Whether you’re here for a romantic getaway, family adventure, or weekend with friends, where you stay can make all the difference.
From historic hotels with skyline views to stylish boutique Airbnbs in walkable neighborhoods, this guide features 25 of the coolest places to stay in Milwaukee — with hyper-local tips from a lifelong Milwaukeean and options for every kind of traveler, from couples and families to wedding parties and girls’ weekends.
👉 Looking for something splash-friendly? Check out our guide to the best downtown hotels with indoor pools.
👉 Want to explore beyond Milwaukee? Don’t miss our list of the Most Unique Places to Stay in Wisconsin for more one-of-a-kind stays around the state.
Boutique Hotels
1. The Iron Horse Hotel
📍 Location: 500 W Florida St, Milwaukee, WI 53204 — Walker’s Point
Vibe: Industrial-chic boutique hotel with serious character
Good for: Parents on a stylish date night, couples who love cool architecture, Harley-Davidson fans
Why it’s cool:
- Set in a 1907 warehouse, now a luxury boutique hotel with exposed brick and polished concrete
- Spacious rooms (400 sq ft+) with custom furniture, local art, and Milwaukee-made finishes
- Onsite restaurant Ash serves modern American cuisine and cocktails on a vibey outdoor patio
- Full-service spa, state-of-the-art fitness center, and walkable access to local restaurants and the Harley-Davidson Museum
- Bonus: It’s pet-friendly and motorcycle-friendly – guests can even roll their bikes inside
👉 Check availability at The Iron Horse Hotel ➝
These stylish stays are the cherry on top of our comprehensive Wisconsin family vacation planner.
2. Saint Kate – The Arts Hotel
139 E Kilbourn Ave, Milwaukee, WI 53202
📍 Location: 139 E Kilbourn Ave, Milwaukee, WI 53202 — Downtown
Vibe: Artsy, upscale, and full of creative energy
Good for: Culture-loving couples, art lovers, parents planning a downtown date night
Why it’s cool:
- One of the most unique hotels in Milwaukee, Saint Kate is an immersive arts experience with local and national artwork in every room
- Set inside a beautifully renovated historic building (originally the 1893 Button Block building)
- Features 219 contemporary rooms and suites with art-forward design and original pieces
- Hosts live performances, exhibits, and rotating installations all year long
- Includes a black box theater, art galleries, and an upscale on-site restaurant
- Walkable to Fiserv Forum, the Marcus Performing Arts Center, Milwaukee Riverwalk, and the Milwaukee Art Museum
👉 Check availability at Saint Kate – The Arts Hotel ➝
3. The Trade Milwaukee
📍 Location: 420 W Juneau Ave, Milwaukee, WI 53203 — Downtown / Deer District
Vibe: Sleek, upscale, and built for modern travelers
Good for: Couples on a foodie getaway, Bucks fans, concert-goers at Fiserv Forum
Why it’s cool:
- One of the newest boutique hotels in Milwaukee, right in the heart of the Deer District near Fiserv Forum
- Designed with luxury and comfort in mind, perfect for event weekends or downtown exploring
- Home to Il Cervo, a rooftop Italian restaurant that’s quickly become one of the best places to eat in Milwaukee
- Standouts include roasted garlic focaccia, handmade pastas, and a dark chocolate torte you won’t forget
- Ideal location for walking to games, shows, and nightlife in Milwaukee’s entertainment hub
👉 Check availability at The Trade Milwaukee ➝
4. The Plaza Hotel
📍 Location: 1007 N Cass St, Milwaukee, WI 53202 — East Town
Vibe: European charm meets vintage art deco
Good for: Quiet getaways, boutique hotel fans, families visiting nearby cultural spots
Why it’s cool:
- A hidden gem in East Town, tucked into a walkable neighborhood near the lakefront and Milwaukee Art Museum
- Vintage art deco design with cozy, apartment-style rooms (each has a kitchenette!)
- The Plaza Café is a local favorite — especially in summer when you can dine in the lush, ivy-covered courtyard
- Easy access to Cathedral Square Park, Veterans Park, the Riverwalk, and downtown attractions
- Feels peaceful and residential while still being in the heart of the city
👉 Check availability at The Plaza Hotel ➝
5. Hotel Metro
📍 Location: 411 E Mason St, Milwaukee, WI 53202 — Downtown
Vibe: Sophisticated, modern, and walkable
Good for: Business travelers, couples on a downtown date night, weekend staycations
Why it’s cool:
- A boutique hotel with modern design, spacious rooms, and upscale amenities
- Features a rooftop terrace, fitness center, stylish lounge, and valet parking
- Easy walking distance to top Milwaukee attractions: the Art Museum, Historic Third Ward, and Harley-Davidson Museum
- Offers a relaxing retreat while keeping you close to the city’s best dining, shopping, and lakefront views
- Ideal for both work trips and romantic weekends
👉 Check availability at Hotel Metro ➝
6. The Pfister Hotel
📍 Location: 424 E Wisconsin Ave, Milwaukee, WI 53202 — Downtown
Vibe: Historic luxury with art, elegance, and a touch of mystery
Good for: Romantic escapes, special occasions, art and history lovers, tea time with a view
Why it’s cool:
- Milwaukee’s most iconic 5-star hotel, dating back to 1893, with opulent Victorian architecture and upscale amenities
- 307 guest rooms (including 82 suites), indoor pool, fitness center, 24-hour business center, and an in-house spa
- Hosts the largest Victorian art collection of any hotel in the world
- The Artist-in-Residence program lets you chat with a working artist in a public studio
- Enjoy morning coffee at the cozy Pfister Café, or sip cocktails high above the city at Blu, the 23rd-floor lounge with panoramic skyline and lake views
- Don’t miss the Afternoon Tea at Blu — it’s one of the most unique tea experiences in the city, complete with live harp music and spectacular views. Read our full guide to Afternoon Tea at The Pfister ➝
- Past guests include Presidents McKinley, Taft, JFK, and Obama, plus countless celebrities
Local Lore:
The Pfister is often called Milwaukee’s most haunted hotel. Many MLB players have shared stories of flickering lights, phantom footsteps, and electronics turning on by themselves. Don’t worry though – it’s more “historic charm” than “haunted house.”
👉 Check availability at The Pfister Hotel
7. Kimpton Journeyman Hotel
📍 Location: 310 E Chicago St, Milwaukee, WI 53202 — Historic Third Ward
Vibe: Trendy, upscale, and effortlessly cool
Good for: Couples, foodie getaways, sports fans, and stylish staycations
Why it’s cool:
- Located in the heart of the Historic Third Ward, steps from the Milwaukee Public Market, art galleries, and some of the city’s best dining
- Stylish rooms with curated décor and luxe touches, true to the Kimpton brand
- Home to The Outsider, a chic rooftop cocktail lounge with one of the best views in the city — perfect for golden hour drinks or cozy firepit hangs
- Keep your eyes peeled: it’s a favorite hotel for NBA teams visiting the Milwaukee Bucks — don’t be surprised to see a team bus parked out front
- Pet-friendly, design-forward, and one of the best boutique hotel experiences in Milwaukee
👉 Check availability at the Kimpton Journeyman Hotel
8. Kinn Guesthouse
📍 Location: 600 N Broadway, Milwaukee, WI 53202 — Downtown
Vibe: Boutique guesthouse meets modern urban retreat
Good for: Couples, solo travelers, business guests, and food lovers exploring Third Ward
Why it’s cool:
- A unique 31-room guesthouse housed in a historic Lawrence Block building—now offering luxurious comfort with residential-style amenities
- Each floor features a fully equipped chef’s communal kitchen, ideal for cooking or gathering
- Includes rooftop event space called The Lookout and cozy tiled meeting rooms
- Located steps from the Milwaukee Public Market, Riverwalk, and boutique shops of the Third Ward
- Downstairs, you’ll find The Wolf on Broadway, a restaurant from the owners of Uncle Wolfie’s. They serve brunch, dinner, and late happy hour in a casual yet stylish dining space—perfect after check-in or travel
- Has a private speakeasy-style lounge on the lower level for late night drinks and live music
Pro Tip: Dining reservations at The Wolf are walk-in only on weekends, and brunch tends to fill quickly—arrive early!
👉 Check availability at Kinn Guesthouse
9. Ambassador Hotel
📍 Location: 2308 W Wisconsin Ave, Milwaukee, WI 53233 — Near Marquette University
Vibe: Art Deco elegance with old Hollywood flair
Good for: Vintage design lovers, architecture buffs, travelers visiting Marquette or attending events
Why it’s cool:
- Built in 1928 with striking Art Deco design, this hotel is full of restored architectural details
- Designed by Milwaukee architect Frederick J. Gaertner, who also designed the iconic Riverside Theater
- Hosted legends like JFK, Eisenhower, Elvis, and Liberace
- Carefully renovated to include modern comforts while preserving its glamorous history
- Offers complimentary shuttle service and easy access to downtown, Fiserv Forum, and the Pabst Mansion
👉 Check availability at the Ambassador Hotel
10. The Brewhouse Inn & Suites
📍 Location: 1215 N 10th St, Milwaukee, WI 53205 — Brewery District
Vibe: Historic, industrial, and beer-lover heaven
Good for: Architecture fans, beer enthusiasts, and travelers looking for something truly Milwaukee
Why it’s cool:
- Housed in the original Pabst Blue Ribbon Brewery, with copper brewing kettles still on display
- Rooms are loft-style with exposed brick, heavy timber beams, and high ceilings
- Don’t miss the stained glass window of King Gambrinus, patron saint of beer
- Walkable to Fiserv Forum, the Pabst Mansion, and the new Brewery District restaurants
- Great for a unique overnight during a Bucks game or brewery tour
👉 Check availability at The Brewhouse Inn & Suites
11. The Knickerbocker on the Lake
📍 Location: 1028 E Juneau Ave, Milwaukee, WI 53202 — Yankee Hill / East Side
Vibe: Classic elegance by the lake
Good for: Longer stays, quiet retreats, and travelers who want a more residential vibe
Why it’s cool:
- Built in the 1920s and listed on the National Register of Historic Places
- Full of original features: marble floors, brass fixtures, ornate lighting
- Located in Yankee Hill, part of Milwaukee’s historic Gold Coast along Lake Michigan
- Most rooms include kitchenettes — great for longer visits or family stays
- Close to Veterans Park, the Oak Leaf Trail, and downtown attractions
👉 Check availability at The Knickerbocker
12. Dubbel Dutch
📍 Location: 817 N Marshall St, Milwaukee, WI 53202 — East Town
Vibe: Historic charm meets indie hotel cool
Good for: Couples, solo travelers, and architecture lovers
Why it’s cool:
- A restored double house from the 1890s, now an intimate 17-room boutique hotel
- Every room is unique, blending antique character with modern comforts
- Features hand-painted walls, local artwork, and a coffee and cocktail bar in the cozy lobby
- Short walk to the Art Museum, Lakefront, Cathedral Square, and summer festivals
- Feels like a secret stay — one of the city’s true hidden gems
👉 Check availability at Dubbel Dutch
13. County Clare Irish Inn & Pub
📍 Location: 1234 N Astor St, Milwaukee, WI 53202 — Lower East Side
⭐ Vibe: Cozy, quirky, and unmistakably Irish
👪 Good for: Pub lovers, travelers seeking charm over polish, Brady Street fans
Why it’s cool:
- Traditional Irish inn and pub with hand-crafted woodwork, rich fabrics, and hearty vibes
- Rooms feature double whirlpool tubs, handcrafted comforters, and Celtic touches throughout
- Just a short stroll to Brady Street, the lakefront, and festival grounds
- Known for its warm hospitality and real-deal Irish breakfasts downstairs
- Great for travelers who want something different than a typical hotel stay
Unique Airbnbs & Vacation Rentals in Milwaukee
Looking for a one-of-a-kind stay in Milwaukee? These thoughtfully designed Airbnbs and VRBOs offer a memorable experience, whether you’re visiting with family, planning a girls’ weekend, or hosting a wedding party.
1. HGTV Renovated Home
📍 Location: Walker’s Point
Vibe: Instagrammable, modern, and designed by a local celeb
Good for: Girls’ weekends, family stays, wedding groups
Why it’s cool:
- Designed by Milwaukee’s own Jenni Yolo (IG DIY expert!) and featured on an HGTV pilot
- Three stylish bedrooms, clawfoot tub, and fenced backyard for pups
- Walkable to bars, restaurants, and event venues
- Fully equipped kitchen and dining space for 8
2. Cream City Victorian
📍 Location: Walker’s Point
Vibe: Historic charm with modern updates
Good for: Large families, bachelorette weekends, friend trips
Why it’s cool:
- Beautifully updated Victorian home that sleeps up to 11 guests
- Includes 3 bedrooms and a pull-out lounger
- Walkable to breweries, bars, and restaurants
- Only a 5-minute Uber from downtown
👉 Book your stay at Cream City Victorian
3. The Bentley Condotel
📍 Location: S 6th St — Walker’s Point
Vibe: Stylish, historic, and group-friendly
Good for: Wedding parties, family reunions, Milwaukee history fans
Why it’s cool:
- Set in an 1892 Cream City brick building by John Bentley
- Features 4 themed apartments, private garden, and free parking
- Near Harley-Davidson Museum, Potawatomi Casino, and MIAD
- 5.6 miles from the airport for easy group arrivals
👉 Check availability at The Bentley Condotel
4. Schlitz Castle
📍 Location: Bay View
Vibe: Grand, quirky, and packed with space
Good for: Large groups, Summerfest visitors, birthday weekends
Why it’s cool:
- Historic home turned luxury VRBO
- Sleeps up to 12 with 5 bedrooms, 4 bathrooms, and 2 kitchens
- Walkable to Bay View bars, restaurants, and wedding venues
- 20+ five-star reviews and plenty of Milwaukee character
👉 Book your stay at the Schlitz Castle
5. The Pink Lady Airbnb
📍 Location: Walker’s Point
Vibe: Feminine, fun, and party-ready (but classy!)
Good for: Bachelorette parties, girls’ getaways, birthday trips
Why it’s cool:
- Instagram-famous with a pink kitchen, champagne bar, and private patio
- Open-concept layout ideal for group hangs
- Note: No parking included, and events must be approved in advance
👉 Check availability at The Pink Lady
6. The White Loft
📍 Location: Downtown Milwaukee
Vibe: Minimalist, airy, and artsy
Good for: Solo travelers, couples, or design-conscious guests
Why it’s cool:
- Combines Mediterranean calm with industrial Milwaukee character
- Located in a historic downtown building
- Refurbished in 2019 with creative, open design
- Perfect for quiet weekends or as a home base for exploring the city
👉 Book your stay at The White Loft
Bed & Breakfasts in Milwaukee
For travelers who prefer a cozy, home-like stay with local flavor, these Milwaukee B&Bs offer charm, hospitality, and personal touches you won’t find in chain hotels. Ideal for romantic weekends, solo getaways, or art-filled adventures.
1. Schuster Mansion Bed & Breakfast
📍 Location: 3209 W Wells St, Milwaukee, WI 53208 — Concordia Neighborhood
Vibe: Grand Victorian charm with a romantic twist
Good for: Couples, history lovers, tea drinkers, and B&B traditionalists
Why it’s cool:
- Built in 1891, this restored Victorian mansion is filled with antique furniture and period details
- Offers nine uniquely decorated guest rooms, each with a private bathroom and free Wi-Fi
- Guests can enjoy a complimentary gourmet breakfast and optional low or high tea service
- Popular for romantic getaways, micro-weddings, and weekend escapes with a touch of old-world elegance
- The warm, welcoming hosts make it feel like staying at a friend’s (fabulous) historic home
👉 Book your stay at the Schuster Mansion
2. The Muse Gallery Guesthouse
📍 Location: 602 E Lincoln Ave, Milwaukee, WI 53207 — Bay View
Vibe: Artsy, colorful, and full of personality
Good for: Solo travelers, couples, creatives, and anyone craving a walkable Bay View stay
Why it’s cool:
- Located in a Victorian-style home built in 1889, right in the heart of Bay View
- Each room is decorated with local art, luxury linens, and modern conveniences (Wi-Fi, Netflix, iHome clock radios)
- Includes a shared community kitchen, free off-street parking, complimentary snacks and beverages
- Don’t miss the wine and cheese welcome hour, free bicycles, and on-site gift shop
- A short walk or bike ride to the lakefront, Bay View coffee shops, and Lincoln Avenue restaurants
👉 Book your stay at The Muse Gallery Guesthouse
Downtown Hotels With Great Locations
Looking for comfort, convenience, and walkability? These downtown Milwaukee hotels put you close to the city’s best attractions, entertainment, dining, and more — perfect for families, business travelers, or anyone who wants to be in the heart of it all.
1. Aloft Milwaukee Downtown
📍 Location: 1230 N Doctor M.L.K. Jr Dr, Milwaukee, WI 53212
Vibe: Modern, playful, and steps from the RiverWalk
Good for: Families, Marquette visitors, and Fiserv Forum event-goers
Why it’s cool:
- Spacious rooms with 9-foot ceilings, large windows, and workstations
- On-site W XYZ Bar, indoor pool, fitness center, and 24-hour snack shop
- Pool tables and a vibrant lounge vibe
- Walkable to Fiserv Forum and just a 9-minute drive to the Art Museum
👉 Check availability at Aloft Milwaukee Downtown
2. Hyatt Regency Milwaukee
📍 Location: 333 W Kilbourn Ave, Milwaukee, WI 53203
Vibe: Polished and professional with skyline views
Good for: Business travelers, pet owners, and conference attendees
Why it’s cool:
- Connected to the Wisconsin Center via skywalk — ideal for events and expos
- 18-story atrium with modern rooms and downtown views
- On-site dining: Bistro 333 and Bar 333 for local bites and craft cocktails
- Close to Milwaukee’s theater district, restaurants, and museums
👉 Book your stay at the Hyatt Regency
3. Hilton Garden Inn Milwaukee Downtown
📍 Location: 611 N Broadway, Milwaukee, WI 53202
Vibe: Historic architecture with modern comfort
Good for: Couples, families, and architecture lovers
Why it’s cool:
- Located inside the iconic Loyalty Building with a stunning 5-story atrium
- Marble, granite, and iron finishes under a glass skylight
- Walkable to the Historic Third Ward, Milwaukee Public Market, and Westown
- Combines big-brand reliability with gorgeous old-Milwaukee vibes
👉 Check availability at Hilton Garden Inn
👉 Planning your visit?
Don’t miss our guide to the Top Attractions in Milwaukee — perfect for mapping out your stay.
Calie Herbst, Editor-in-Chief of Milwaukee With Kids, has spent over a decade combining her experiences as a parent of three to create a hub for Milwaukee’s family adventures.
Her decade-long teaching career in Milwaukee Public Schools and academic background, including a Master’s in Teaching from Marquette University and dual B.A.s in Sociology and Spanish from the University of Wisconsin – Madison, fuel her passion for inclusive and engaging family content.
Calie is also a recognized voice in local media, contributing to WISN Channel 12 News, WTMJ Wisconsin Morning News, Fox 6’s Real Milwaukee, and B93.3.
Discover more about Calie’s journey and editorial approach on her About Page and Editorial Policy Page.
