Weekend Getaways in Wisconsin
Weekend getaways in Wisconsin are some of the best in the Midwest. I love all the unique destinations, favorite spots, and underrated gems that keep me coming back.
Weekend getaways in Wisconsin are some of the most unique and refreshing escapes in the Midwest. They’re easily among my favorite ways to enjoy lakes, small towns, and scenic countryside!
Whether you’re looking for outdoor adventure, cozy relaxation, or historic charm, Wisconsin has some of the best weekend trip options around.
What makes Wisconsin so special is the variety. You can spend the day kayaking on a crystal-clear lake, hiking forest trails, or wandering through an artsy downtown filled with local shops and breweries. Add in incredible food (like amazing cheese, farm-to-table dining, and craft beer) and you’ve got all the ingredients for a perfect weekend getaway.
From the lakefront beauty of Door County to the rolling hills of the Driftless Area, from Madison’s lively cultural scene to the underrated charm of towns like Bayfield, each destination feels unique.
With four true seasons, every trip has its own flavor, whether it’s a snowy winter escape or a summer lakeside retreat.
For me, Wisconsin isn’t just about where you go. It’s about the warm hospitality, local flavor, and unique experiences that make each weekend trip feel special.
Best Romantic Weekend Getaways in Wisconsin:
Grand Geneva Resort and Spa
We drove a little over an hour southwest from Milwaukee, the road cutting through farmland and rolling hills before reaching Lake Geneva.
There was something instantly grounding about Grand Geneva. Tucked into rolling hills and forested trails, Grand Geneva Resort and Spa felt like a world unto itself, where we could just be.
Grand Geneva Resort & Spa in Lake Geneva, Wisconsin, is one of my favorite Midwest getaways and honestly feels like a hidden gem when it comes to year-round resorts.
Originally built as a Playboy Club Hotel in the 1960s, the property has transformed into a luxurious retreat that balances history, charm, and modern comfort.
I loved how expansive the resort felt—set on 1,300 acres of rolling hills, with a lake, golf courses, ski slopes, and walking trails, it truly feels like its own destination.
My favorite feature was the stunning views from nearly every corner of the property, whether I was relaxing in my room, playing a round of golf, or sitting by the fire pits at sunset.
The accommodations are spacious and stylish, with cozy beds, fireplaces in some rooms, and balconies overlooking the beautiful grounds.
For me, one of the best parts of the stay was the WELL Spa + Salon. I indulged in a massage and spent time unwinding in the relaxation lounges—it was the perfect escape.
What makes Grand Geneva special is how much there is to do in every season. In the summer, I loved lounging by the outdoor pool and taking advantage of the lake activities.
In the winter, the ski hill and ice skating rink made it feel like a snowy retreat. The resort also offers two championship golf courses, award-winning dining, and plenty of family-friendly amenities.
For me, Grand Geneva Resort & Spa is one of the best all-season resorts in the Midwest—a perfect blend of relaxation, recreation, and understated luxury.
It’s easily one of my favorite escapes when I want a mix of adventure and serenity.
To book, check availability or prices for Grand Geneva Resort and Spa.
Milwaukee - Saint Kate - The Arts Hotel
We drove in from the lakefront in just a few minutes, the streets lined with theaters and old brick buildings as we reached the center of downtown.
Saint Kate – The Arts Hotel wasn’t just a hotel, it was an experience. Art was everywhere: on the walls, in the rooms, in the energy. We wandered from gallery to cocktail bar to live jazz in the lounge, completely wrapped in color and inspiration.
Saint Kate – The Arts Hotel in Milwaukee, Wisconsin, is easily one of my favorite boutique hotels in the Midwest, and I think it’s one of the most underrated gems for travelers who love creativity and culture.
From the moment I walked in, I felt like I had stepped into a living art gallery—the entire hotel celebrates the arts in every form, from visual installations to live performances.
What I loved most was how the hotel seamlessly blends luxury with artistic expression.
The lobby is filled with rotating exhibits and thought-provoking pieces, and even the hallways showcase contemporary art. My room felt like a creative retreat, with sleek modern design, curated artwork, and cozy yet stylish touches.
My favorite detail was the record player with a selection of vinyls—it gave the stay such a fun, personal vibe.
Saint Kate goes beyond being just a hotel, it’s an experience.
I enjoyed sipping craft cocktails at the bar while listening to live music, and I loved exploring the on-site galleries that highlight both local and national artists.
The dining options were another highlight, especially their restaurant ARIA, which offered inventive dishes with a Midwest twist.
The location in downtown Milwaukee made it easy for me to walk to theaters, museums, and the RiverWalk, but honestly, I could have spent all weekend inside the hotel itself and still felt inspired.
For me, Saint Kate – The Arts Hotel is more than just a place to stay.
It’s vibrant, imaginative, and unforgettable, a true hidden treasure that has quickly become one of my favorite boutique hotels anywhere.
To book, check availability or prices for Saint Kate – The Arts Hotel.
Bayfield - Old Rittenhouse Inn
We drove north along the shore of Lake Superior, the road curving through forests and small towns before opening to the harbor at Bayfield.
Bayfield was quiet and crisp, the kind of small town that makes you want to walk slowly and speak softly. At Old Rittenhouse Inn, we stepped back in time, clawfoot tubs, stained glass windows, and candlelit breakfasts.
The Old Rittenhouse Inn in Bayfield, Wisconsin, is one of my favorite historic inns and truly a hidden gem on the shores of Lake Superior.
This charming Victorian mansion feels like stepping back in time, with its beautifully preserved architecture, warm hospitality, and cozy atmosphere that makes every stay special.
I loved how the inn combines historic character with comfort.
My room was filled with antique furnishings, stained-glass windows, and a fireplace that made it feel so inviting.
My favorite feature was the sweeping view of Lake Superior—waking up to that sparkling water was unforgettable.
Some rooms even have whirlpool tubs and private balconies, which add an extra touch of romance and relaxation.
One of the best parts of staying at the Old Rittenhouse Inn is the dining. Their on-site restaurant is known for creative, locally inspired cuisine, and breakfast each morning was a highlight.
I loved starting my day with homemade pastries, fresh fruit, and hearty dishes, all served in a beautiful dining room with lake views. The location in Bayfield is also perfect.
I could stroll to quaint shops, galleries, and the ferry to Madeline Island, or simply relax on the inn’s wraparound porch with a glass of wine and watch the world go by.
In autumn, the fall colors are spectacular, and in summer, the lake feels alive with activity.
For me, the Old Rittenhouse Inn is the best of Bayfield—historic, welcoming, and full of charm. It’s easily one of my favorite escapes in Wisconsin and a truly underrated treasure on Lake Superior.
To book, check availability or prices for Old Rittenhouse Inn.
The Delafield Hotel
We drove west from Milwaukee in about half an hour, the highway giving way to rolling countryside before we reached the small town of Delafield.
There was a clean elegance to Delafield, the way the light hit the brick buildings, the way The Delafield Hotel blended history with modern grace. It felt grown-up and grounding, a place where romance didn’t need a soundtrack.
The Delafield Hotel in Delafield, Wisconsin, is one of my favorite boutique luxury hotels in the Midwest, and I think it’s an underrated gem that deserves more attention.
Tucked just outside Milwaukee, it offers the perfect mix of small-town charm and sophisticated comfort.
What I loved most was the elegance of the rooms.
Each one feels more like a private residence than a hotel stay, with soaring ceilings, rich wood accents, plush furnishings, and spa-like bathrooms that often feature oversized soaking tubs and walk-in showers.
My favorite detail was the mix of classic design with modern luxury—it created a space that felt both cozy and indulgent.
The hotel also has one of the best dining experiences in the area.
Its on-site restaurant, I.d., is known for creative, seasonal dishes and a lively atmosphere.
I loved relaxing there in the evening with craft cocktails and inventive small plates—it felt like a destination on its own.
Another highlight for me was the location. The Delafield Hotel sits right in the heart of downtown Delafield, with charming boutiques, coffee shops, and galleries just steps away.
It’s also close to beautiful trails, lakes, and the Kettle Moraine State Forest, which made it easy to pair luxury with outdoor adventure.
For me, The Delafield Hotel is one of the best boutique stays in Wisconsin—stylish, welcoming, and full of character.
Whether for a romantic weekend, a foodie getaway, or simply a serene escape, it’s easily one of my favorite hidden treasures in the Midwest.
To book, check availability or prices for The Delafield Hotel.
Sturgeon Bay - The Holiday Music Motel - 2 hours 25 min from Milwaukee, WI
Stepping into The Holiday Music Motel was like opening a vinyl sleeve and hearing the needle drop. It had a rhythm all its own, bright colors, vintage vibes, and just enough kitsch to make you grin.
The Holiday Music Motel in Sturgeon Bay, Wisconsin, is one of my favorite quirky, hidden gems in Door County.
It’s not your typical hotel—it’s actually the only fully operational motel in the U.S. that’s also dedicated to supporting and celebrating music.
I loved how it combines retro charm with a creative spirit, making it one of the most unique places I’ve ever stayed.
The vibe here is pure 1950s Americana, with a fun mid-century design that feels both nostalgic and playful.
My room had vintage-inspired décor, cozy furnishings, and modern comforts that made it super comfortable.
My favorite touch was the old-school radio in the room that actually played local broadcasts featuring musicians connected to the motel—such a cool way to tie the theme together.
What I think makes this place really special is its connection to the local music scene.
The Holiday Music Motel hosts songwriting festivals and music events throughout the year, like the Steel Bridge Songfest, where artists come together to collaborate and perform.
I loved the feeling that I was part of something creative just by staying there.
The location is another highlight, you’re right in downtown Sturgeon Bay, within walking distance of shops, galleries, restaurants, and the waterfront.
It made exploring Door County super easy, while still having a cozy, welcoming place to come back to.
For me, The Holiday Music Motel is more than just a stay—it’s an experience.
It’s underrated, full of character, and one of my favorite spots in Wisconsin for anyone who loves music, history, and a little retro flair.
To book, check availability or prices for The Holiday Music Motel.
Fish Creek - Thorp House Inn and Cottages - 3 hours from Milwaukee, WI
We drove north along the peninsula from Sturgeon Bay in about forty minutes, the road lined with cherry orchards and glimpses of the bay.
Fish Creek was all dappled light and gently swaying trees, and Thorp House Inn and Cottages felt like it had been waiting for us. Our cottage creaked in the loveliest way, and the mornings smelled like pine and coffee.
The Thorp House Inn and Cottages in Fish Creek, Wisconsin, is one of my favorite hidden gems in Door County, and I think it’s one of the most underrated places to stay in the area.
Dating back to the 1800s, this charming inn has a rich history and perfectly captures the cozy, welcoming spirit of Door County.
I loved how the property is split between the main inn and several private cottages.
The inn itself is filled with historic character—antique furnishings, inviting parlors, and a warm, homelike atmosphere.
My room felt both elegant and comfortable, with thoughtful touches that made it hard to leave in the mornings.
My favorite feature, though, was the cottages.
They offered a bit more privacy, complete with kitchens, living rooms, and porches, making them perfect for longer stays or family getaways.
The location is one of the best parts. Right in the heart of Fish Creek, the Thorp House is just steps from boutiques, restaurants, and the waterfront, yet it still feels tucked away and peaceful.
I loved being able to stroll down to the harbor or head into Peninsula State Park for a day of hiking and exploring.
Breakfast at the inn was another highlight, with homemade treats and fresh coffee served in a cozy dining area.
It felt like starting the day in a friend’s home rather than a hotel.
For me, the Thorp House Inn and Cottages is a true Door County treasure—romantic, historic, and wonderfully welcoming.
It’s easily one of my favorite places to stay when I want the perfect blend of charm, comfort, and location.
To book, check availability or prices for Thorp House Inn and Cottages.
Where the Moments Feel More Meaningful
Whether it’s the golden light over Lake Geneva or the hush of snow outside a Door County cottage, Wisconsin has a way of deepening even the smallest romantic moments. These getaways remind us that love often lives in shared stillness, laughter by candlelight, or simply the chance to linger with no rush at all. Wherever you choose to go, let the journey bring you closer, to your partner, and to yourself.
My personal highlights:
Some of my favorite Wisconsin weekend getaways include Door County for its lighthouses and shoreline views, Madison for its mix of college-town energy and lakeside fun, and the underrated town of Bayfield as a gateway to the Apostle Islands.
Each one offers the best blend of scenery, culture, and relaxation.
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.
