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.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Oostburg

Pet friendly

Apartment

Pool

Condo

Hot tub

Family friendly

Cottage

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Oostburg hotels

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

A modern restaurant with wooden accents, white tiled walls, and yellow chairs.

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

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

1. Fairfield Inn & Suites by Marriott Sheboygan

Sheboygan

Kari

฿4,115

฿4,670 total

includes taxes & fees

4 Oct - 5 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 a sofa, a small round table, a bed, a desk, and a lamp.

A modern dining area with a long table and colorful chairs, a kitchen with dark cabinets, and a fruit display.

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

2. Comfort Inn & Suites Sheboygan I-43

Sheboygan

Chelsea

฿2,664

฿3,024 total

includes taxes & fees

8 Oct - 9 Oct

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

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

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.

3. AmericInn by Wyndham Sheboygan

Sheboygan

Angelica

฿2,908

฿3,300 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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.

4. Watershed Hotel

Sheboygan

David

฿4,292

฿4,872 total

includes taxes & fees

1 Oct - 2 Oct

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

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

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

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

5. Holiday Inn Express Sheboygan-Kohler by IHG

Sheboygan

Ryan

฿4,440

฿5,040 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 swimming pool with a no diving sign, chairs around it, and a max pool capacity sign.

6. Grandstay Residential Suites Hotel - Sheboygan

Downtown Sheboygan

Kristin

฿3,454

฿3,920 total

includes taxes & fees

27 Sept - 28 Sept

A hotel with a curved facade, illuminated signage, and snow-covered surroundings.

A cozy living room with a fireplace, leather furniture, and a chandelier.

A coastal golf course with a view of the ocean.

A spa area with a green heated floor, a ceiling with a cloud mural, and two relaxation chairs on either side.

7. Inn On Woodlake

Kohler

MARTHA

฿12,499

฿13,811 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

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

8. La Quinta Inn by Wyndham Sheboygan

Sheboygan

Tony Michael Williams

฿2,981

฿3,384 total

includes taxes & fees

8 Oct - 9 Oct

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

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

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

A Super 8 motel with a red roof, brick facade, and a signboard.

9. Super 8 by Wyndham Sheboygan WI

Sheboygan

Jessica

฿2,368

฿2,688 total

includes taxes & fees

27 Sept - 28 Sept

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

A restaurant with multiple tables and chairs, large windows, and a view of the outside.

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

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

10. Harbor Winds Hotel

Sheboygan

janice

฿3,449

฿3,915 total

includes taxes & fees

4 Oct - 5 Oct

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

A hotel dining area with tables, chairs, a reception desk, and a ceiling fan.

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.

11. Quality Inn Sheboygan North I-43

Sheboygan

Christine

฿2,635

฿2,990 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

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

12. Baymont by Wyndham Plymouth

Plymouth

Paula

฿4,343

฿4,930 total

includes taxes & fees

5 Oct - 6 Oct

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

13. AmericInn by Wyndham Plymouth

Plymouth

Amy

฿3,917

฿4,446 total

includes taxes & fees

15 Sept - 16 Sept

A spacious atrium with a grand chandelier, multiple balconies, and large windows allowing natural light.

A beachfront hotel with multiple red-roofed buildings, a sandy path leading to the beach, and clear blue water.

A large, white building with a symmetrical facade and multiple balconies.

A spacious lobby with a central chandelier, multiple levels with balconies, and rows of blue chairs.

14. Blue Harbor Resort and Conference Center

Sheboygan

Laura

฿6,052

฿7,736 total

includes taxes & fees

9 Sept - 10 Sept

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

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

A reception area with two counters, a marble wall, an ATM, and a staircase.

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

15. The Oasis Hotel & Bar

Sheboygan Falls

Pamela Baker

฿2,339

฿2,584 total

includes taxes & fees

4 Oct - 5 Oct

A large, historic building with multiple chimneys and a prominent American flag.

A spacious indoor area with multiple seating arrangements, including chairs and sofas, and a bar area with shelves.

A large indoor pool with a waterfall feature, surrounded by white chairs and a large towel rack.

16. The American Club

Kohler

Ken

฿21,215

฿23,443 total

includes taxes & fees

20 Sept - 21 Sept

17. Inn of Sheboygan

Downtown Sheboygan

Anonymous traveller

฿32,892

฿37,332 total

includes taxes & fees

22 Sept - 23 Sept

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 buffet counter with a coffee machine, a display case with food, and a digital menu board.

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

18. Home2 Suites By Hilton Sheboygan

Sheboygan

Teresa

฿4,558

฿5,174 total

includes taxes & fees

4 Oct - 5 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.

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

Port Washington

Mark

฿5,583

฿7,205 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 conference room with a long table, six chairs, and a wooden accent wall.

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

A hotel room with two beds, a desk, a chair, a TV, and an air conditioning unit.

20. Wingate by Wyndham Sheboygan

Downtown Sheboygan

Hannah

฿2,808

฿3,187 total

includes taxes & fees

8 Oct - 9 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Oostburg attractions

Whispering Pines Amphitheater

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

See properties

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.

See properties

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.

See properties

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.

See properties

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

A coastal beach with a lighthouse, pier, and grassy dunes.

Top Oostburg Hotel Reviews

Quality Inn Sheboygan North I-43

8/10 Good

"clean room friendly staff"

Super 8 by Wyndham Sheboygan WI

10/10 Excellent

"Every thing was Clean, and the AC work very god I rest like queen after a long trip."

Grandstay Residential Suites Hotel - Sheboygan

8/10 Good

"Smaller pool and exercise room, but offers them versus other hotels that don't. Overall, great location as it was close to everything, pharmacy, food, etc."

Comfort Inn & Suites Sheboygan I-43

8/10 Good

"Staff were great but hotel seemed a bit dated in the halls and rooms."

Watershed Hotel

10/10 Excellent

"This was an absolutely wonderful place. The staff was excellent and very helpful. We were able to walk to other places safely, although most of the restaurants were 3/4 of a mile away or more. I would absolutely recommend this hotel!"

Wingate by Wyndham Sheboygan

8/10 Good

"We were there a short time. A fan was drying the carpet in the hallway. Overall an acceptable room."

La Quinta Inn by Wyndham Sheboygan

10/10 Excellent

"Nothing fancy but for a room we only slept in it was clean and the staff were helpful."

The Harborview on Lake Michigan, an Ascend Collection Hotel

10/10 Excellent

"Beautiful views! Walking paths excellent. Restaurant breakfast was delicious.. Highly recommend"

Harbor Winds Hotel

10/10 Excellent

"Super cute hotel on the river. Staff was very friendly too. Was pleasantly surprised for the price and would come back again."

More cheap stays in Oostburg

The Oasis Hotel & Bar

600 N Main St Sheboygan Falls WI

฿2,339

฿2,584 total

4 Oct - 5 Oct

includes taxes & fees

8/10 Very good! (416 reviews)

Super 8 by Wyndham Sheboygan WI

3402 Wilgus Avenue Sheboygan WI

฿2,368

฿2,688 total

27 Sept - 28 Sept

includes taxes & fees

6.6/10 (868 reviews)

Quality Inn Sheboygan North I-43

4332 N 40th St Sheboygan WI

฿2,635

฿2,990 total

4 Oct - 5 Oct

includes taxes & fees

8/10 Very good! (847 reviews)

Comfort Inn & Suites Sheboygan I-43

3912 Motel Rd Sheboygan WI

฿2,664

฿3,024 total

8 Oct - 9 Oct

includes taxes & fees

Motel 6 Saukville, WI

180 S. Foster Drive Saukville WI

฿2,795

฿3,145 total

13 Sept - 14 Sept

includes taxes & fees

6.8/10 (873 reviews)

Grandstay Residential Suites Hotel - Sheboygan

708 Niagara Avenue Sheboygan WI

฿3,454

฿3,920 total

27 Sept - 28 Sept

includes taxes & fees

8.6/10 Excellent! (1,083 reviews)

Frequently asked questions

What's the best place to stay in Oostburg?

Grandstay Residential Suites Hotel - Sheboygan, located 10 mi (16.1 km) from the heart of Oostburg, is a top choice for your stay, based on our traveller data. Other good options for your stay in the area are Watershed Hotel and AmericInn by Wyndham Sheboygan. See all available top hotels, or vacation rentals in Oostburg.

If I need to cancel my hotel reservation in Oostburg, will I receive a refund?

Yes, most hotel reservations are refundable if you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you have a non-refundable reservation, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Oostburg.

What are some hotels with pools in Oostburg?

AmericInn by Wyndham Sheboygan: Hotel located near Lake Michigan. Offers daily, an indoor pool and free self parking. View all hotels with pools in Oostburg.

What's it like to stay in Oostburg?

Travellers to Oostburg will find plenty to explore and enjoy. A top sight in the city is Lake Michigan. In Oostburg, there are 32 hotels and other accommodation options to choose from. Find out more about Oostburg.

What are the top places to visit in Oostburg?

Favourite places to visit include Lake Michigan, Kohler-Andrae State Park and Oostburg Public Library. A couple of additional sights to add to your itinerary are Veteran's Park and Cedar Grove Hawk Research Station State Natural Area. Take a look at what more there is to see and do in Expedia's Oostburg guide.

What's the seasonal weather like in Oostburg?

The hottest months are usually August and July, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Oostburg are January, March, February and October, with each month seeing an average of 17 cm of snowfall.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Oostburg on Expedia.com

Find hotels in Oostburg, WI from ฿2,584

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Oostburg

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Oostburg hotels

1. Fairfield Inn & Suites by Marriott Sheboygan

2. Comfort Inn & Suites Sheboygan I-43

3. AmericInn by Wyndham Sheboygan

4. Watershed Hotel

5. Holiday Inn Express Sheboygan-Kohler by IHG

6. Grandstay Residential Suites Hotel - Sheboygan

7. Inn On Woodlake

8. La Quinta Inn by Wyndham Sheboygan

9. Super 8 by Wyndham Sheboygan WI

10. Harbor Winds Hotel

11. Quality Inn Sheboygan North I-43

12. Baymont by Wyndham Plymouth

13. AmericInn by Wyndham Plymouth

14. Blue Harbor Resort and Conference Center

15. The Oasis Hotel & Bar

16. The American Club

17. Inn of Sheboygan

18. Home2 Suites By Hilton Sheboygan

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

20. Wingate by Wyndham Sheboygan

Stay near popular Oostburg attractions

Whispering Pines Amphitheater

Oostburg Public Library

Cedar Grove Hawk Research Station State Natural Area

Veteran's Park

Learn more about Oostburg

Top Oostburg Hotel Reviews

Quality Inn Sheboygan North I-43

Super 8 by Wyndham Sheboygan WI

Grandstay Residential Suites Hotel - Sheboygan

Comfort Inn & Suites Sheboygan I-43

Watershed Hotel

Wingate by Wyndham Sheboygan

La Quinta Inn by Wyndham Sheboygan

The Harborview on Lake Michigan, an Ascend Collection Hotel

Harbor Winds Hotel

More cheap stays in Oostburg

The Oasis Hotel & Bar

Super 8 by Wyndham Sheboygan WI

Quality Inn Sheboygan North I-43

Comfort Inn & Suites Sheboygan I-43

Motel 6 Saukville, WI

Grandstay Residential Suites Hotel - Sheboygan

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app