Vacation rentals with outdoor seating in Sheboygan County

Lakefront Charmer, cheerful decor gorgeous garden

This 2600 sqft lakefront home is a spacious retreat year round, friendly to kids and dogs. It is perched upon a bluff overlooking Lake Michigan with a gorgeous sunrise view. In winter, enjoy passing cargo ships and eagles along with ice formations. Inside, dine with seating and service for 12 after cooking in the spacious kitchen with wood fireplace. Kitchen, living room, dining room and 2 bedrooms have full lake view. 2 large screen tvs. Spa quality bath with whirlpool. Gas fireplace too!

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

The Hemingway on Church - It Tolls For Thee

"Kristine's property has all the charm of a modern day Mayberry" -Michael This 1906 historic home is nestled in the heart of the equally historic "Village of Kohler." Completely remodeled in 2019 adding Kohler spa amenities and modern touches to its original charm. Mixing modern & antique furniture finds like the Hemingway Sideboard (which inspired the literary theme) make this historic hideaway a true Kohler destination. "You cannot get a better location in Kohler than this house!" -Dennis

Blue Barn on the Green and Farmhouse Retreat

Imagine your perfect countryside escape. Nestled on five acres of farmland, this serene retreat offers tranquility and breathtaking views. Enjoy fishing, paddle boarding, or simply relaxing by the pond. For the golf enthusiasts, we're just a short drive from downtown Kohler and other top-rated courses. Our property is ideal for families, couples, or groups seeking a peaceful retreat. We also host unforgettable weddings in this idyllic setting. Contact us today to book your dream getaway!

hot tub and sauna on 5 private acres

Need a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your inspired getaway awaits!

Woodland Creek Retreat: explore & relax!

Lovely home nestled in 9 acres of peaceful woodland. 1.5 miles off I-43. Enjoy a walk in the woods or enjoy the dunes and wonderful views of Lake Michigan from Terry Andrae State Park only .2 miles away! Enjoy relaxing on the front porch or taking in the view of the woods from the spacious back deck. Be on the lookout for turkeys and deer. Wonderful wood burning fireplace and extensive game collection(500+) for staying in! We love the cozy and open cabin feel and hope you will too!

Boutique Wellness Retreat - Hot Tub and Fireplace

Enjoy this beautifully boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom with King size bed. Secondary bedroom has 2 twin beds. The beautiful fireplace in the living room is perfect for a relaxing couples evening. Enjoy a glass of wine or local brew on the patio while you grill out. EV Charger and E-Bikes to explore the area. Sonos audio throughout. This beautiful boutique home is sure to impress!

Logan's Guest Nest

Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

Beachside Lake View - 2br - First Floor - Garage

Located just one lot in from the beautiful shores or Lake Michigan. Amazing location provides year round stunning views . This is a lower 2 bedroom 1 bath condo in a 4unit building were all the units have the same basic layout. You can listen to the waves or walk just a few feet and have the sand on your feet. This condo features front and rear balconies. Makes for a great place to enjoy a weekend get away or a place to relax at night while on a business trip.