Vacation rentals with outdoor seating in Sheboygan

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Top-rated outdoor seating rentals in Sheboygan

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Oostburg

4.97 out of 5 average rating, 234 reviews

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

Mar 1 – 8

G$31,713 GYD per night

Guest favorite

Home in Sheboygan

4.96 out of 5 average rating, 154 reviews

Dog Friendly Blue Door Cottage / Fully Fenced Yard

Nobody should have to leave their fur baby behind while on vacation. This is exactly why we created this comfortable home with your family & puppy in mind. You'll be at ease knowing that your pooch will be having just as much fun as you are. Modern hints are complemented by the cozy, welcoming decor found throughout. The coffee bar is a fav for any morning person, and the "take-a-wine leave-a-wine" wine bar offers evening excitement! The huge yard features a fire pit, gas grill, & cornhole.

Jan 9 – 16

G$28,331 GYD per night

Guest favorite

Home in Sheboygan

4.99 out of 5 average rating, 190 reviews

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!

Oct 17 – 24

G$59,121 GYD per night

Guest favorite

Home in Plymouth

4.97 out of 5 average rating, 165 reviews

Wyatt's Country Home - King Bed!

Soak up the modern vintage charm of our fully remodeled and updated home! Thank you for choosing our sparkling clean space. Our home is nestled on two quiet acres just north of Plymouth in the peaceful country. Enjoy coffee as the sun rises from one of the two decks, or perhaps a cocktail by the fire as the sun sets. We ourselves lived in this home for our first 5 years and turned it into a beautiful and peaceful space for ourselves that we would now like to share with everyone.

Nov 14 – 21

G$23,290 GYD per night

Guest favorite

Home in Sheboygan

4.94 out of 5 average rating, 103 reviews

Relaxing Riverfront Retreat

Beautiful home on the Sheboygan River in the heart of Sheboygan. With its central location it is a short distance to the downtown, lakefront, and area attractions. You will enjoy the outside as much as the inside. Relax on the patio or around the fire pit taking in the view of the river. Fishing, kayaking, or canoeing are also options. One level living with three large bedrooms; one queen, two twins, and a full, with TVs in each. Large full bathroom complete with washer and dryer.

Oct 18 – 25

G$42,805 GYD per night

Guest favorite

Home in Campbellsport

4.99 out of 5 average rating, 138 reviews

Gleason's Chouse

You'll love staying in our unique home, in a quiet neighborhood. This is a recently remodeled 1867 church converted to a "Chouse". Featuring 2 bedrooms, Full Kitchen, 1 Bathroom, Balcony, Parking, and a Gazebo.. all beautifully complimented by a range of antiques and decorations. 8 Miles East of Hwy 41, a 45 min drive to Oshkosh or an hour to Milwaukee. Just down the from Lake Bernice & Eisenbahn Bike Trail. Also close enough to the Kettle Moraine Forest to hike and sightsee!

Sep 24 – Oct 1

G$26,734 GYD per night

Guest favorite

Home in Sheboygan

4.97 out of 5 average rating, 151 reviews

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.

Jul 23 – 30

G$30,826 GYD per night

Guest favorite

Apartment in Kohler

5.0 out of 5 average rating, 158 reviews

Church Street Romance & Retreats-Village of Kohler

“A well-appointed, cozy and stylish retreat close to everything in Kohler.” -Kim Take the stairs to my secluded 2nd floor tree view retreat! A private side entrance and open floor plan flanked by two bedrooms makes this unit perfect for couples or a girl's getaway spa weekend. Romantic turn-of-the-century touches meet modern convenience & comfort. Baker furniture, previously a Kohler Company, can be found throughout the apartment enhancing your Village of Kohler stay.

Oct 31 – Nov 7

G$35,881 GYD per night

Guest favorite

Condo in Sheboygan

4.87 out of 5 average rating, 192 reviews

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.

Nov 24 – Dec 1

G$30,751 GYD per night

Guest favorite

Home in Sheboygan

4.94 out of 5 average rating, 172 reviews

Beachfront getaway in Sheboygan

One of the few homes in Sheboygan that walks out onto the sands of Lake Michigan, this 3 bedroom/ 2 bath home is meant for total relaxation and fun. The open kitchen, dining and living room is full of light from the sliding glass doors on the back of the house, which access a deck and a large back yard. Upstairs is a spacious loft with a pull out couch. Fire pit in the back yard. Just steps from a playground at King Park. Amazing sunrises, worth waking up for.

Oct 3 – 10

G$63,975 GYD per night

Guest favorite

Home in Glenbeulah

4.98 out of 5 average rating, 112 reviews

Stay at Sunrise LLC, Like being at Grandma's

Welcome to Stay at Sunrise LLC. We offer a clean and comfortable home for your vacation enjoyment. We are in a rural farm area, the recreation trail head is 3 miles east of us as well as the Wade House, we are near the Kettle Moraine State Forest and the Ice Age Trail and 7 miles from Road America. Large yard, Fire pit, picnic table, child swing set. Garage parking on site if arranged in advance. Smoking is allowed outside of the home. No pets allowed.

Feb 17 – 24

G$18,050 GYD per night

Guest favorite

Home in Sheboygan

4.97 out of 5 average rating, 117 reviews

Lake Michigan home with gorgeous views!

Our beautiful lakefront home is perfect for bringing everyone together - Ladies weekend, guys golf trip, family reunion, Packers games...this is your place. Minutes to downtown Sheboygan/Kohler, with 5 star PGA championship golf courses (Black Wolf Run, Whistling Straits, The Bull of Pinehurst), Kohler Waters Spa, and the beaches/dunes of Kohler Andrae State Park. Renovated bedroom and movie room completed early 2020.

Oct 30 – Nov 6

G$123,831 GYD per night