Weekend Getaways in Wisconsin
I found weekend getaways in Wisconsin to be full of variety and charm. Within just a few hours’ drive, you can explore rolling farmlands, sparkling lakes, historic small towns, and vibrant cities with thriving food and arts scenes.
One of the best parts for me on my three week road trip was discovering the perfect lakeside cabin, cozy inn, or boutique hotel to make your base while you explore. Here are some unique accommodations I came across that I think you’ll enjoy on your Wisconsin adventures. Whether you get away for just a night or a weekend, these places will help you return more relaxed and refreshed.
1. Grand Geneva Resort and Spa
Just an hour from Milwaukee, this expansive, full-service resort is set amid 1,300 acres of rolling countryside near Lake Geneva. I loved how it blends elegance with contemporary comfort. The design embraces a warm, lodge-inspired aesthetic with stone accents, vaulted ceilings, and expansive windows framing views of the golf course and surrounding nature.
My two-night stay in a spacious guest room (a Premier King with Balcony) at Grand Geneva Resort and Spa featured plush, high-thread-count linens, a marble bathroom with walk-in rainfall shower, a private balcony overlooking the grounds, and a serene color palette inspired by natural woods and earth tones. The thoughtful amenities—like an in-room Keurig, oversized soaking tub, and deluxe bath products—made it feel both upscale and homely.
Around the resort, I discovered two championship golf courses, a world-class spa, multiple dining venues, indoor and outdoor pools, a modern fitness center, ski slopes in winter, and miles of scenic hiking trails. I especially appreciated the resort’s family-friendly touches, seasonal activities, and pet-friendly policies, which make it welcoming for all types of travelers.
Things to do near the resort include walking along the Geneva Lake Shore Path, relaxing at Riviera Beach, or exploring Big Foot Beach State Park.
To book, check availability or prices for Grand Geneva Resort and Spa.
My favorite moment was dinner at Ristorante Brissago, where authentic Northern Italian cuisine is served in an intimate, romantic setting.
2. Milwaukee - Saint Kate - The Arts Hotel
Right in Milwaukee so that we didn't have to travel far, this boutique design hotel is a true creative gem! From the moment you step inside, you’re immersed in a world where hospitality meets the arts. The sleek, contemporary design is elevated by rotating exhibitions, performance spaces, and thought-provoking installations scattered throughout the property, giving the entire hotel a gallery-like feel. It’s upscale, inspiring, and full of character.
My guest room for the night (a King Room with City View) struck the perfect balance between modern comfort and artistic flair. It featured minimalist yet chic furnishings, curated artwork from local creators, hardwood floors, plush bedding with crisp linens, and playful touches like an in-room record player and a selection of vinyls to set the mood. The bathrooms boasted walk-in showers, luxury bath products, and stylish finishes, adding to the boutique vibe.
Beyond the rooms, Saint Kate offers a variety of vibrant spaces to explore: a theater for live performances, multiple on-site art galleries, a modern fitness center, and a buzzing lobby bar that feels like a cultural hub. The hotel also embraces its artsy identity through curated experiences, from workshops to special exhibits, making every stay unique.
To book, check availability or prices for Saint Kate – The Arts Hotel.
My favorite were the gallery spaces that showcase Milwaukee’s vibrant art scene because it felt like both a hotel stay and a cultural journey. It truly makes it one of the best weekend getaways in Wisconsin!
3. Bayfield - Old Rittenhouse Inn
This historic Victorian mansion turned boutique B&B has timeless charm and plenty of character! Perched on a hill overlooking Lake Superior, the inn exudes old-world elegance with its grand woodwork, stained-glass windows, and antique furnishings. I thought this was one of the best romantic weekend getaways in Wisconsin. Why? The atmosphere is cozy, romantic, and steeped in history—perfect for a quiet getaway in Bayfield.
We drove 4 hours from Minneapolis and checked into a Fireplace King room with Lake View for two nights. Our romantic room was was both elegant and inviting. It featured period-style décor, a four-poster bed with soft linens, a private fireplace for cozy evenings, and large windows framing gorgeous views of the lake. The en-suite bathroom included a whirlpool tub, plush robes, and luxury bath amenities that elevated the historic charm with a touch of modern comfort.
The inn also offers intimate common areas, including a library lounge, parlor rooms, and a fine dining restaurant. Its Landmark Restaurant is one of Bayfield’s culinary highlights, offering gourmet breakfasts for guests and exquisite dinners with a focus on fresh, locally sourced ingredients. The overall experience feels like stepping back in time, but with all the comforts of boutique hospitality.
To book, check availability or prices for Old Rittenhouse Inn.
My favorite was the historic ambiance, from antique décor to lake views and cozy fireplaces.
4. The Delafield Hotel
The Delafield Hotel is located just outside Milwaukee and combines classic elegance with a modern sense of style. Its stately red-brick exterior and refined interiors set the stage for an upscale, intimate experience. Inside, the hotel balances traditional charm with contemporary design touches—think grand wood accents, rich fabrics, and sleek details—all creating a polished yet inviting atmosphere.
My guest room for the night (a Deluxe King Suite) was spacious and indulgent, designed with comfort and sophistication in mind. It featured a plush four-poster bed dressed in fine linens, a lavish marble bathroom with a spa tub and walk-in rainfall shower, elegant furnishings, and thoughtful details like soft robes and high-end bath products. The overall feel was both luxurious and serene, perfect for a restful retreat.
The hotel also impresses with its I.d. Restaurant, known for inventive, seasonal cuisine and artful plating, as well as its stylish bar for evening cocktails. Guests can enjoy a well-equipped fitness center, meeting spaces, and proximity to the charming shops and cafes of downtown Delafield. The property offers a boutique feel with five-star touches, making it equally suited for romantic getaways, weddings, or executive stays.
To book, check availability or prices for The Delafield Hotel.
My favorite was dining at I.d. Restaurant, where the menu features creative, chef-driven dishes with a focus on local ingredients.
5. Sturgeon Bay - The Holiday Music Motel - 2 hours 25 min from Milwaukee, WI
The Holiday Music Motel: Quirky, retro, and full of character—this motel is unlike anywhere else you’ll stay in Door County! Known as the world’s only fully operational motel with a working recording studio, it’s a haven for musicians and music lovers alike. The property has a vintage 1950s vibe, with colorful décor, neon signs, and a playful mid-century modern aesthetic that makes the experience feel both nostalgic and unique.
We drove 2 hours and 15 minutes from Milwaukee and checked into the hotel for one night. My guest room (a Standard Queen) was simple yet stylish, featuring retro furnishings, cozy bedding, and playful touches like bright accent walls and kitschy artwork. While not luxury in the traditional sense, it offered everything I needed for a comfortable stay, along with a strong dose of personality. The rooms are pet-friendly, and the vibe is more about community and creativity than frills.
What makes the Holiday Music Motel truly special is its music-first culture. The motel frequently hosts songwriting festivals, jam sessions, and live performances in partnership with its in-house Tambourine Lounge. Guests may even stumble upon spontaneous music-making in the lobby or courtyard, adding to its one-of-a-kind charm.
To book, check availability or prices for The Holiday Music Motel.
My favorite was the live music scene, from scheduled events to the impromptu jam sessions.
6. Fish Creek - Thorp House Inn and Cottages - 3 hours from Milwaukee, WI
Nestled in the heart of charming Fish Creek, just under 3 hours from Milwaukee, this historic 19th-century inn offers a romantic, storybook setting with all the warmth of a classic Door County escape. The main house, a beautifully preserved Victorian, exudes timeless character with wraparound porches, period antiques, and inviting sitting rooms. The atmosphere is tranquil and intimate, making it a perfect choice for couples or anyone seeking a slower, more nostalgic pace.
We stayed in one of the inn’s elegant romantic guest rooms for a night, which featured a cozy queen bed dressed in crisp linens, antique furnishings, and a gas fireplace that set a wonderfully romantic tone. Many rooms include whirlpool tubs, private balconies, and views of the garden or village. For more privacy, the on-site cottages are a delightful alternative, each with fully equipped kitchens, charming décor, and porches that let you soak up Fish Creek’s small-town charm over the weekend.
Breakfast is a highlight here: a generous spread of homemade pastries, fresh fruit, and hot dishes served each morning in the cheerful dining room. The inn is also perfectly located—you can stroll to boutiques, galleries, and the waterfront, or venture just minutes away to explore Peninsula State Park.
To book, check availability or prices for Thorp House Inn and Cottages.
My favorite part were the cottages, which combine the charm of a vintage Door County stay with the practicality of private kitchens and porches.
Conclusion
From romantic Victorian inns and boutique luxury hotels to quirky music-themed motels and cozy lakeside cottages, Wisconsin offers a wonderfully diverse range of weekend escapes. Whether you’re seeking fine dining and spa indulgence, a creative arts-inspired stay, or a relaxed retreat close to nature, there’s truly something for every type of traveler.
Booking Checklist
1. Book Your Flight - I use Expedia because I like their mobile app with my itinerary. They've helped me re-book flights on many occasions. Once you reach their Gold tier, support is especially good.
2. Book Your Hotel - I use Booking.com or Expedia, depending on my destination.
3. Book Your Rental Car - I use Expedia.
4. Book your tours on Viator or Get Your Guide.
