Oostburg Holiday Rentals, Wisconsin: Private House Rentals

A wooden dock extending into a calm body of water, with boats docked nearby and a building with a red roof in the background.

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Our top choices for Oostburg hotels

A modern interior with a stone fireplace, seating area, and a flat-screen TV mounted above it.

A modern building entrance with glass doors, a covered walkway, and a view of a green landscape.

A modern interior with a stone fireplace, large windows, and a flat-screen TV above it.

A modern hotel with a flat roof, large windows, and a sign reading "The Watershed."

1. Watershed Hotel

Sheboygan

Brian

Rp2.336.341

Rp2.651.747 total

includes taxes & fees

4 Oct - 5 Oct

A spacious living area with a fireplace, a sofa, and a dining area in the background.

A spacious dining area with multiple wooden tables and chairs, a ceiling fan, and a bar area in the background.

A hotel room with two beds, a sofa, a TV, and a dining table.

A GrandStay hotel with a modern design, featuring a prominent entrance and a clear view of the parking area.

2. Grandstay Residential Suites Hotel - Sheboygan

Downtown Sheboygan

Kristin

Rp1.879.815

Rp2.133.590 total

includes taxes & fees

27 Sept - 28 Sept

An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled deck.

A reception area with a Baymont Inn & Suites sign, a reception desk, a small round table, and a decorative wreath.

A hotel room with a flat-screen TV, a desk with a chair, a bed, a sofa, and a large window with curtains.

A hotel room with two beds, a desk with a computer, a TV, and a window with curtains.

3. Baymont by Wyndham Plymouth

Plymouth

Paula

Rp2.364.091

Rp2.683.243 total

includes taxes & fees

11 Oct - 12 Oct

A hotel with a modern design, featuring a prominent tower with the hotel name, a covered entrance, and a well-maintained lawn.

A hotel room with two beds, a desk, a chair, a sofa, and a round yellow table.

A hotel room with a sofa, a small round table, a bed, a desk, and a lamp.

An indoor swimming pool with clear water, tiled floor, and safety railings.

4. Comfort Inn & Suites Sheboygan I-43

Sheboygan

Chelsea

Rp1.450.143

Rp1.645.913 total

includes taxes & fees

18 Oct - 19 Oct

A modern hotel lobby with a TV, wooden paneling, a round light fixture, and a reception desk.

A modern dining area with a dark wooden table and matching stools, a grey carpet, and a wall-mounted artwork.

A modern kitchen with white cabinets, a black tiled backsplash, stainless steel appliances, and a wooden floor.

A living room with two sofas, a coffee table, and a lamp. Large windows with curtains are on the walls, and the room has a carpeted floor.

5. Plymouth Suites Hotel

Plymouth

Grace

Rp1.740.172

Rp1.975.095 total

includes taxes & fees

27 Sept - 28 Sept

A modern kitchen with a marble countertop, a coffee machine, and various food items displayed.

A modern hotel bathroom with a large mirror, a sink, and a shower area.

A modern living room with a sofa, armchairs, and a coffee table.

A spacious lobby with a wooden staircase, a reception desk, and a seating area.

6. La Quinta Inn by Wyndham Sheboygan

Sheboygan

Tony Michael Williams

Rp1.764.520

Rp2.002.731 total

includes taxes & fees

25 Oct - 26 Oct

A restaurant with stone walls, a flat-screen TV, a fireplace, and a kitchen area with a water dispenser and coffee machines.

A spacious hotel lobby with a central kitchen area, a staircase, and a seating area with a sofa and a small table.

7. AmericInn by Wyndham Plymouth

Plymouth

Amy

Rp2.309.487

Rp2.621.267 total

includes taxes & fees

26 Oct - 27 Oct

An indoor swimming pool with wooden walls and ceiling, surrounded by white lounge chairs and tables.

A hotel room with a bed, a sofa, a desk, and a painting on the wall.

A hotel room with a bed, a sofa, a desk, and a television.

A pathway leading to a building with a patio area, surrounded by sunflowers and marigolds.

8. Quality Inn Sheboygan North I-43

Sheboygan

Christine

Rp1.638.483

Rp1.859.677 total

includes taxes & fees

18 Oct - 19 Oct

A modern hotel entrance with a curved canopy, multiple floors, and a prominent sign.

An outdoor patio with stone walls, a fire feature, and seating.

A reception area with a wooden reception desk, a digital display, and a refrigerator stocked with beverages.

A swimming pool with a lifeguard sign, lounge chairs, and a view of the outdoors.

9. Fairfield Inn & Suites by Marriott Sheboygan

Sheboygan

Napolean

Rp2.239.665

Rp2.542.020 total

includes taxes & fees

4 Oct - 5 Oct

A kitchen with dark cabinets, a wooden countertop, and pendant lights.

A view of a bridge with a tower, a river, and a sunset sky.

A waterfront hotel with a prominent sign, a flagpole, and a reflection in the water.

A hotel room with two beds, a desk, a chair, a TV, and framed pictures on the walls.

10. Harbor Winds Hotel

Sheboygan

janice

Rp1.861.908

Rp2.113.265 total

includes taxes & fees

4 Oct - 5 Oct

An indoor swimming pool with clear blue water, tiled walls, and large windows offering a view of a field.

A neatly made bed with white bedding, two bedside lamps, a dark headboard, and a small bedside table with a phone and a lamp.

A bar area with a long counter, multiple stools, and a selection of beverages.

A spacious lobby with marble flooring, vending machines, and a staircase.

11. The Oasis Hotel & Bar

Sheboygan Falls

Shane

Rp1.272.903

Rp1.406.558 total

includes taxes & fees

4 Oct - 5 Oct

An outdoor patio area with tables and chairs, string lights, and a view of the building in the background.

An indoor swimming pool with a geometric ceiling design, a seating area with chairs, and a view of the outdoors through large windows.

A modern hotel room with two beds, a desk, and a view of the outdoors.

A multi-story hotel with a modern design, featuring a covered outdoor seating area and a visible fire feature.

12. Home2 Suites By Hilton Sheboygan

Sheboygan

Susan

Rp2.334.193

Rp2.649.309 total

includes taxes & fees

4 Oct - 5 Oct

An indoor swimming pool with lounge chairs and tables, a clear blue pool, and a high ceiling with visible structural beams.

A restaurant with multiple dining tables, chairs, and a bar area.

A reception area with a wooden reception desk, a flat-screen TV, and a seating area with two chairs and a small table.

A conference room with a long table, six chairs, and a wooden accent wall.

13. Wingate by Wyndham Sheboygan

Downtown Sheboygan

Joell

Rp1.654.237

Rp1.877.560 total

includes taxes & fees

19 Oct - 20 Oct

A hotel room with two beds, a desk, and a window with a view of a parking lot.

A bathroom with a sink, mirror, towel rack, and toiletries.

A laundry room with two washing machines, a storage door, and a control panel.

A reception desk with a digital screen, a sign indicating check-in times, and a door.

14. Super 8 by Wyndham Sheboygan WI

Sheboygan

Dana

Rp1.700.785

Rp1.930.480 total

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with wooden cabinets, a dining table, and a coffee machine.

A living room with a sofa, a small table, and a TV mounted on the wall. There are two wall-mounted lights and a large potted plant.

A spacious living area with wooden flooring, a dining set, a TV, and a refrigerator.

A two-story house with a well-maintained lawn and flower beds.

15. Belgium Inn & Suites

Belgium

Jose

Rp1.595.157

Rp1.794.776 total

includes taxes & fees

4 Oct - 5 Oct

A reception area with a wooden counter, a welcome sign, a no smoking sign, and various items on shelves.

A motel with a red exterior, multiple rooms, a parking lot, and surrounding greenery.

A bathroom with a sink, mirror, towel rack, and a wall-mounted light fixture.

16. Bonne Belle Motel

Kewaskum

jennifer

Rp1.187.864

Rp1.253.196 total

includes taxes & fees

1 Oct - 2 Oct

A spacious living area with a stone fireplace, comfortable seating, and a balcony with a railing.

A coffee station with a chalkboard sign reading "Welcome to the Beginning of Day!" and various coffee-making equipment.

A hotel room with a bed, a desk with a sink, a chair, a small table, and a window with curtains.

A reception area with two desks, a TV, and orange chairs.

17. AmericInn by Wyndham Sheboygan

Sheboygan

Thomas

Rp1.582.625

Rp1.796.281 total

includes taxes & fees

4 Oct - 5 Oct

A Holiday Inn Express hotel with a brick facade, a covered entrance, and an American flag.

A modern dining area with a central island, bar stools, and a sofa.

An indoor swimming pool with clear blue water, surrounded by white chairs and tables, and large windows offering views of the outdoors.

A hotel room with two beds, a wooden headboard, bedside tables with lamps, and a small shelf.

18. Holiday Inn Express Sheboygan-Kohler by IHG

Sheboygan

Ryan

Rp2.488.517

Rp2.824.556 total

includes taxes & fees

4 Oct - 5 Oct

A spacious kitchen with dark wooden cabinets, a central island, and a dining area with a brown leather chair.

A dining table with food items, a microwave, and a couch in a living room.

A cozy living room with a brown leather sofa, a wooden coffee table, and a large window with curtains.

A restaurant with wooden flooring, tables, and chairs. There is a television mounted on the wall and a window with a view outside.

19. The Port Hotel

Port Washington

steve

Rp3.358.961

Rp3.812.444 total

includes taxes & fees

11 Oct - 12 Oct

A patio with tables and chairs, a red umbrella, and a view of a body of water and buildings.

A bar area with a long counter, multiple stools, and hanging light fixtures.

A modern interior with wooden flooring, a bar area with stools, and a seating area with tables and chairs.

A multi-story hotel with a docked boat, a waterfront view, and a clear sky.

20. The Harborview on Lake Michigan, an Ascend Collection Hotel

Port Washington

Joseph

Rp2.571.766

Rp3.391.235 total

includes taxes & fees

18 Oct - 19 Oct

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Stay near popular Oostburg attractions

Cedar Grove Hawk Research Station State Natural Area

This scientific landmark has tracked raptor migrations since the 1950s, banding over 38,000 birds from 24 species. Witness researchers at work during fall migration when hawks soar overhead in impressive numbers.

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Oostburg Public Library

This welcoming community hub houses over 32,000 volumes and hosts regular educational programmes for all ages. Browse the diverse collection or join a creative writing camp for an enriching local experience.

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Whispering Pines Amphitheater

You can make plans for a show at Whispering Pines Amphitheater on your trip to Oostburg.

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Veteran's Park

Veterans Park honours local heroes with its community-focused bandshell, built in 2007. Bring a blanket for summer concerts or attend the annual Augustfest celebrations in this peaceful Oostburg gathering space.

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Learn more about Oostburg

Discover things to see and do in Oostburg as you venture to popular sights like Lake Michigan.

See all hotels in Oostburg

Top Oostburg Hotel Reviews

The Oasis Hotel & Bar

8/10 Good

"The rooms are clean however it is an old property and smells food a lot. Lot of construction workers but beds were okay. Not for families. Fine for single guys...if you just want to sleep for a night"

Blue Harbor Resort and Conference Center

10/10 Excellent

"It was so special! Clean fun!"

Holiday Inn Express Sheboygan-Kohler by IHG

10/10 Excellent

"-"

Quality Inn Sheboygan North I-43

8/10 Good

"Pleased that a room was ready even though we arrived much earlier than expected. Housekeeping came in one of the days (we forgot to put out the DND sign) but they provided fresh towels and toiletries without disturbing or rearranging any of our personal items. Much appreciated."

AmericInn by Wyndham Sheboygan

8/10 Good

"The proper"

Super 8 by Wyndham Sheboygan WI

8/10 Good

"Fair pricing, been in worse for a lot more money. Beds were a bit hard, showers were hot, reserved an accessable room, apparently that means it's on the first floor. No grab bars in the shower or by the toilet. Good for the price."

Siebkens Resort

10/10 Excellent

"Enjoyed the Historic hotel. Wonderful staff. Nice to go breakfast offering. Food at Pam’s was wonderful. Hostess was very good to us. We came in late and many menu items were sold out. They still took care of us well."

La Quinta Inn by Wyndham Sheboygan

10/10 Excellent

"Great location. Great price. Great room."