Oostburg vacation rentals

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Top-rated vacation rentals in Oostburg

Guests agree: these vacation 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, 233 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.

Feb 11 – 18

G$31,609 GYD per night

Guest favorite

Home in Howards Grove

4.95 out of 5 average rating, 151 reviews

Spacious lower level priv entrance no cleaning fee

Entire basement is for rent with a separate entrance. Kitchen area includes refrigerator, microwave, coffee pot, toaster, sink, dining table and chairs. NO STOVE OR OVEN IS AVAILABLE. Free Wifi and Cable TV. Air conditioning. Plenty of parking, keyless entry. 14 min to Road America, 13 min to Kohler, 9 min to Whistling Straits, 5 min to Lakeland University, 1 hr to Milwaukee, 1 hr to Green Bay. Lots of nice amenities, clean, spacious. No cleaning fee. Unit NOT set up for babies or toddlers.

Aug 12 – 19

G$22,602 GYD per night

Guest favorite

Home in Sheboygan

4.96 out of 5 average rating, 153 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.

Mar 4 – 11

G$28,238 GYD per night

Guest favorite

Home in Oostburg

4.96 out of 5 average rating, 138 reviews

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan completely private surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room and living room entertainment space, den with see thru log fired fireplace, screened in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and row boat are available for the boating enthusiast, with life jackets and other floating devices.

Nov 27 – Dec 4

G$59,479 GYD per night

Guest favorite

Apartment in Sheboygan

4.92 out of 5 average rating, 398 reviews

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

Jan 20 – 27

G$17,130 GYD per night

Guest favorite

Home in Oostburg

4.98 out of 5 average rating, 157 reviews

River Ridge-HOT TUB, Games, Luxury, 8 bed, 5 STARS

The search is over, you have found the PERFECT getaway at River Ridge South! The moment you pull in, you will become instant hero for planning the ultimate retreat. This property has something for everyone! Beautiful seclusive country home (3800 sq ft) on 4 acres of a pristine and manicured lawn with the Onion River passing through it. This home is THE perfect countryside retreat for large group gatherings with three levels of finished space and great outdoor amenities.

Dec 20 – 27

G$194,655 GYD per night

Guest favorite

Guesthouse in Oostburg

4.9 out of 5 average rating, 258 reviews

Beach House

This guesthouse is detached from the main house and comes with garage parking and has all the amenities you want including a wood-burning fire place! Towels, bath tissue, soaps and travel items. AC Window Unit. Kitchen includes pots/pans, dishes, mugs/glasses, coffee pot, toaster and microwave. Paper goods and hand sanitizer included. New appliances and new water heater in 2020. The beach is steps away with a fire pit, boat house lounge, kayaks, beach toys and bicycles.

Jan 28 – Feb 4

G$46,428 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.

Dec 7 – 14

G$34,322 GYD per night

Guest favorite

Home in Oostburg

4.96 out of 5 average rating, 164 reviews

Shamba on the Lake, Oostburg, WI

Large guest home , in a rustic setting, on a peaceful 2-acre wooded lot (only 5 homes on a very private road) on Lake Michigan with a large private beach a few feet from the deck. . Magnificent panoramic view, amazing sunrises, serene twilights, magical star-studded night skies. A slice of Paradise you must experience. Located a mile from I43, 40 minutes from downtown Milwaukee, 20 mins. from golf courses in Kohler, 30 mins. from Road America in Elkhart Lake...

Nov 20 – 27

G$79,143 GYD per night

Guest favorite

Apartment in Sheboygan

4.84 out of 5 average rating, 183 reviews

Sheboygan Surf House "Jetties"

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our Urban living oasis is a fully equipped studio apartment conveniently located in the heart of downtown, just steps from bars and restaurants and only blocks to Lake Michigan South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake, Kite boarding, charter fishing, a Wedding or leisure time SSH is perfect for you. Support Dog friendly

Dec 18 – 25

G$13,406 GYD per night

Superhost

Guesthouse in Sheboygan

4.83 out of 5 average rating, 367 reviews

Carriage House Sheboygan, Lake Mich beach access!

The Carriage House is the perfect getaway. Located in a beautiful historic neighborhood with Lake Michigan public beach access across the street, 100 yards away. Ideal for a family of four or an individual in town for business. Amenities have been thoughtfully placed to create the most comfortable and convenient stay for guests. We pride ourselves on ensuring you enjoy your stay with us and guarantee you'll love the neighborhood!

Oct 16 – 23

G$22,341 GYD per night

Guest favorite

Apartment in Waldo

4.98 out of 5 average rating, 259 reviews

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.

Mar 22 – 29

G$22,245 GYD per night