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Wisconsin is known for its work hard, play hard mentality, and what better way to enjoy time off than with a stay in a beautiful Wisconsin resort.
Everyone deserves an occasional break away from the stresses of daily life. Whether to an urban oasis or a remote destination surrounded by the great outdoors, there are many ways to indulge in some R&R in Wisconsin.
And what’s especially great about America’s Dairyland is that it rocks four distinct seasons. As the weather changes from month to month, so too does the landscape. From sunshine and lush forests in the summer to fiery foliage in the fall and snow-covered trees in the winter, the wilderness of Wisconsin has something for everyone.
With a stay in one of these best resorts in Wisconsin, you can treat yourself to a luxurious getaway while experiencing the ever-changing beauty of the state.
Related Read: 14 Best Things to Do in Wisconsin in Every Season
1. Canoe Bay
Why you should stay: An all-inclusive lakeside resort perfect for couples seeking a reprieve in nature.
- Nearest city: Chetek
- Class: Four star
- Recent recognition: Voted #1 Resort in the Midwest in Conde Nast’s “2016 Readers’ Choice Awards”
- Rates start from: $348/night
Experience the charm of knotty pine cottages surrounded by 300-acres of sprawling Wisconsin landscape at Canoe Bay. Family is at the heart of this locally owned and operated outdoor resort founded about 30 years ago.
This adults-only resort can be found along the banks of Dead Goose Lake, where guests can soak up some sunshine, enjoy a refreshing dip in the calm waters, and partake in more active lake activities like fishing and kayaking. This neck of the woods also offers fantastic golf opportunities at Sioux Creek and Turtleback courses and downhill skiing at nearby Blue Hills Ski Resort.
Check AvailabilityFollow ‘em: @CanoeBayRelaisChateaux
2. Grand Geneva Resort & Spa
Why you should stay: Play, ski, and relax to your heart’s content at this modern resort in southern Wisconsin.
- Location: Lake Geneva
- Class: Four star
- Recent recognition: AAA Four-Diamond resort
- Rates start from: $159/night
Whether you’re looking for a family-friendly vacation or a romantic getaway for two, the Grand Geneva Resort & Spa is brimming with incredible amenities for everyone. Once the site of a Playboy Club Hotel, today, the grounds have been updated to feature architecture inspired by Wisconsin’s own Frank Lloyd Wright.
Not to mention, the resort boasts ski slope access, an onsite waterpark perfect for kiddos, and five dining options. For those interested in some pampering, a visit to the resort’s WELL Spa is a must. You’ll find this comprehensive resort conveniently located a few miles away from the bustle of downtown Lake Geneva and some of the region’s top golf courses.
Check AvailabilityFollow ‘em: @Grand_Geneva
3. The Osthoff Resort
Why you should stay: An upscale resort on the shores of Elkhart Lake offering private suites with one to three bedrooms.
- Location: Elkhart Lake
- Class: 3.5 stars
- Recent recognition: AAA Four-Diamond
- Rates start from: $180/night
There’s no need to journey to the seaside as The Osthoff Resort is a charming lakeside attraction that embodies the spirit of the east coast. Although the current iteration of the Osthoff opened its doors in 1995, this beautiful resort has been a popular tourist destination for city folk as far back as the late 1880s.
Travelers from all over come to indulge in lake activities, the resort’s private Aspira Spa, multiple swimming pools, and whirling hot tubs. The Osthoff is only a few miles from top Wisconsin attractions like the Henschel’s Indian Museum and the Road America Racetrack.
Check AvailabilityFollow ‘em: @OsthoffResort
4. The Edgewater
Why you should stay: A sophisticated boutique hotel in downtown Madison not far from the state capitol building and the Memorial Union Terrace.
- Location: Madison
- Class: Four star
- Recent recognition: AAA Four-Diamond
- Rates start from: $179/night
Modern amenities and retro elegance collide at The Edgewater, Madison’s beautiful 1940’s resort hotel on the banks of Lake Mendota. Known for its incredible lake views, many choose to stay at The Edgewater to enjoy upscale suites.
When you’re not off enjoying the fabulous culinary scene downtown Madison is famous for, the hotel’s onsite dining, serving sophisticated dishes and casual offerings, is sure to please. Other amenities include a well-appointed gym, a spa, and a wellness center. In the winter, the resort’s outdoor terrace is transformed into a magical ice rink and a place to gather around blazing fire pits.
Check AvailabilityFollow ‘em: @TheEdgeH2O
5. The Pfister Hotel
Why you should stay: A luxurious Victorian hotel that’s been in business for over 125 years and has become an iconic landmark in Milwaukee.
- Location: Milwaukee
- Class: Four star
- Recent recognition: AAA Four-Diamond and Historic Hotels Worldwide®
- Rates start from: $250/night
Opulence and grandeur await you at the historic Pfister Hotel, an urban resort that’s recognized for its historical significance. One step inside, and you’ll be awed by the gilded accents and incredible mural on the vaulted ceiling. According to their website, The Pfister holds “the largest Victorian art collection of any hotel in the world.”
Aside from the rich history and impeccable interior design, the resort also features an indoor pool, fitness center, internationally recognized onsite dining, and a martini bar on the 23rd floor. The Pfister is in a prime spot within walking distance to Milwaukee’s Historic Third Ward and Lake Michigan
Check AvailabilityFollow ‘em: @ThePfisterHotel
6. Sundara Inn & Spa
Why you should stay: An intimate wellness spa with only 34 guest rooms and private villas on a quiet 90-acre property filled with fresh scented pines.
- Location: Wisconsin Dells
- Recent recognition: Top 10 Midwest Resort Hotels in Travel + Leisure magazine’s “World’s Best Awards” for 2021
- Rates start from: $369/night
At Sundara Inn & Spa, wellness and relaxation are the primary focus, and this philosophy shows in their incredible spa offerings. Treat yourself to a day of salt treatment therapy, massages, body treatments, nails, and more. When you’re not at the spa, you’re sure to be relaxing in the resort’s indoor to outdoor freeform swimming pool with a swim-up bar. There are two other outdoor pools, one of which has an infinity edge.
When dinner rolls around, head over to Nava, Sundara’s onsite restaurant for fresh dishes that utilize locally sourced and organic ingredients. The water parks and restaurants of downtown Wisconsin Dells are about a ten-minute drive away.
Check AvailabilityFollow ‘em: @sundara.spa
7. Stout’s Island Lodge
Why you should stay: An outdoor resort that offers lodge accommodation or private cabins on two little islands in the center of Red Cedar Lake.
- Location: Birchwood
- Class: Two star
- Rates start from: $189/night
Wake up every morning to the sights and sounds of lapping waves at Stout’s Island Lodge, a unique island getaway in northern Wisconsin. The entire resort sits on two connected islands, one 12-acres, and the other 5.7-acres, promoting a secluded and quiet lake getaway. Visitors must take the resort’s pontoon ferry to reach the islands, which leave once every hour during the day.
Everything you need during your stay is on the islands, from outdoor lawn games to canoes and kayaks and miles of hiking trails. The main lodge serves up complimentary breakfast as well as local Midwestern cuisine. Guests can also arrange trips back to the mainland to partake in local golf and other outdoor attractions.
Check AvailabilityFollow ‘em: @StoutsIslandLodge
8. Holiday Acres Resort
Why you should stay: A quaint and budget-friendly Wisconsin resort immersed in the Northwoods a short drive from the village of Rhinelander.
- Location: Rhinelander
- Class: Three star
- Rates start from: $95/night
Head Up North for a classic backcountry stay at the Holiday Acres Resort. Open since 1949, this resort on Lake Thompson has always been a family affair. Experience the untouched wilderness of the surrounding Northwoods with your very own cozy cottage, or book a room in the historic lodge close to the resort’s main amenities.
The resort has a main restaurant that serves local and international fare and a cafe that offers casual dishes. The resort also features a gift shop, an indoor heated pool, and a cedar sauna for utmost relaxation. The best outdoor activities at Holiday Acres include fishing for walleye, relaxing on the beach, and renting a pontoon bike.
Check AvailabilityFollow ‘em: @HolidayAcresResort
9. The American Club Resort Hotel
Why you should stay: A sophisticated hotel that holds the title for the only five-star resort in Wisconsin known for its highly-rated golf courses.
- Location: Kohler
- Class: Five star
- Recent recognition: AAA Five-Diamond Resort
- Rates start from: $352/night
Red brick and Tudor-style architecture wow at The American Club Resort Hotel. This glamorous resort was once a dormitory for employees of the historic Kohler Corporation but now offers upscale accommodation for those seeking utmost comfort in an elegant setting. Surrounded by popular golf courses like Blackwolf Run and The Bull at Pinehurst Farms, the property sits outside of Sheboygan just ten minutes from Lake Michigan.
Outside of the main brick building, there are even more accommodation options at the neighboring Carriage House. It’s here you can also book sessions at the Kohler Waters Spa, sit beside a bonfire on the rooftop terrace, and soak in the hot tub.
Check AvailabilityFollow ‘em: @TheAmericanClub
10. Justin Trails Resort
Why you should stay: A bed and breakfast resort on a sprawling 200 acres of farmland in Wisconsin’s Driftless Region.
- Location: Sparta
- Class: Three stars
- Rates start from: $229/night
Justin Trails Resort provides rest and relaxation in the countryside with a stay in their rustic yet homey cabins and farmhouse suites. A classic red barn and rolling greenery greet you as you drive up, creating a picturesque atmosphere. Dogs are more than welcome and will enjoy the miles of dog-friendly walking and snowshoeing trails on the resort grounds.
You’ll also find a disc golf course, fire pits, and three cute llamas roaming the farm. All bookings include a hot and fresh breakfast in the lodge. There are other noteworthy dining options in the nearby village of Sparta. Justin Trails is about a 35-minute drive from La Crosse.
Check AvailabilityFollow ‘em: @JustinTrails
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Seen in: Lodging, Midwest, Resorts, Where to Stay, Wisconsin
