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

Oostburg Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Oostburg vacation rentals

A living room with a fireplace, a large clock, and a dining area with wooden furniture.

1. Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Oostburg

Cheryl

AED 508 total

includes taxes & fees

16 Nov - 17 Nov

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

2. Grandstay Residential Suites Hotel - Sheboygan

Downtown Sheboygan

Vivian

AED 438 total

includes taxes & fees

12 Nov - 13 Nov

A bedroom with a wooden headboard, a bed with grey bedding, a fireplace, and a clock displaying 6:00.

3. Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Ellis Historical District

Terri

AED 321 total

includes taxes & fees

18 Nov - 19 Nov

A hallway leading to a room with a wooden floor, a white door, and a painting of sailboats on the wall.

4. Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

Sheboygan

Heidi

AED 636 total

includes taxes & fees

15 Nov - 16 Nov

A spacious living room with a sofa, armchairs, a coffee table, and a TV mounted on the wall. There is a dining area in the background with a table and chairs.

5. 3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

Sheboygan

Brian L.

AED 671 total

includes taxes & fees

27 Nov - 28 Nov

A narrow hallway with a bench, pillows, and a potted plant.

6. Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Sheboygan

Benjamin B.

AED 655 total

includes taxes & fees

18 Nov - 19 Nov

A bathroom with white shelves holding wicker baskets and a potted plant.

7. Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

Sheboygan

Stephanie K.

AED 675 total

includes taxes & fees

12 Nov - 13 Nov

A living room with a coffee station, a sofa, a ceiling fan, and a view of the outdoors.

8. Sleeps 8 & Spacious!

Sheboygan

Dean M.

AED 1,403 total

includes taxes & fees

8 Dec - 9 Dec

A spacious living room with a sofa, coffee table, and a TV. There is a ceiling fan, a fireplace, and a large window.

9. The Beach town bungalow

Sheboygan

A spacious living area with a wooden dining table, chairs, and a sofa. There is a staircase leading to another level, and a large window providing natural light.

10. Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Downtown Sheboygan

Andrea L.

A two-story house with a front porch, a well-maintained lawn, and a sidewalk leading to the street.

11. Logan Ave Holiday House - Upper

Sheboygan

Alex N.

AED 1,233 total

includes taxes & fees

10 Dec - 11 Dec

A modern living room with a grey sofa, a white armchair, a round coffee table, and a side table with a lamp.

12. Beautiful & Convenient!

Sheboygan

Susan J.

AED 1,314 total

includes taxes & fees

10 Dec - 11 Dec

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

13. The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

Sheboygan

Jean S.

14. Beachfront Paradise: King Suite - Sleeps 8!

Sheboygan

Nina S.

AED 2,281 total

includes taxes & fees

9 Dec - 10 Dec

A deck with a view of a lake, surrounded by various signs and advertisements.

15. Victorian Inn Elkhart Lake Wisconsin

Elkhart Lake

Deirdre

AED 2,099 total

includes taxes & fees

12 Nov - 13 Nov

A beach with pebbles, a wooden structure, and several birds.

16. Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

Sheboygan

Nicole B.

A living room with a sofa, coffee table, and TV.

17. Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Sheboygan

Maggie A.

AED 2,105 total

includes taxes & fees

13 Nov - 14 Nov

A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

18. The Links! - Luxury Golf Retreat with Golf Simulator

Sheboygan

Kristian N.

19. Just Beachy: 4 Bedroom, Sleeps 12!

Sheboygan

Erika M.

20. Edgewater Villa: 4 Bedroom, Sleeps 14!

Sheboygan

Rebecca B.

AED 2,889 total

includes taxes & fees

11 Dec - 12 Dec

View all properties

Find vacation rentals that suit your style

Top Oostburg Hotel Reviews

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

Fairfield Inn & Suites by Marriott Sheboygan

Sheboygan

10/10 Excellent

My 6 year old daughter and I were taking our first "mother-daughter" vacation to Sheboygan for a few days. We were originally reserved to stay at a nearby hotel. That experience was a nightmare (extremely dirty hotel room, "upgraded" to another dirty room, terrible customer service, etc.) and it looked like I was going to have to cancel our trip and my daughter was very upset. At the last minute, there was an opening at Fairfield Inn that my husband was able to reserve for us. He had been...

Jenny

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

Comfort Inn & Suites Sheboygan I-43

Sheboygan

10/10 Excellent

Michelle

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

AmericInn by Wyndham Sheboygan

Sheboygan

10/10 Excellent

Gina

Grandstay Residential Suites Hotel - Sheboygan

Downtown Sheboygan

10/10 Excellent

Adam

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

Harbor Winds Hotel

Sheboygan

10/10 Excellent

jim

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

Inn On Woodlake

Kohler

10/10 Excellent

Dennis

AmericInn by Wyndham Plymouth

Plymouth

10/10 Excellent

Rob

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

Baymont by Wyndham Plymouth

Plymouth

10/10 Excellent

Anonymous traveler

A two-story white building with green shutters, a front porch, and a staircase leading to the upper floor.

The Rochester Inn, A Historic Hotel

Sheboygan Falls

10/10 Excellent

Anonymous traveler

A restaurant with multiple tables set for dining, featuring white tablecloths and floral centerpieces.

Siebkens Resort

Elkhart Lake

10/10 Excellent

We wanted to take a night off in the country away from the Chicago area and our favorite two hour away place is Elkhart Lake, WI. We were upgraded to a 2 bedroom condo due to an issue in the reserved room. The condo had a fireplace, kitchen, a tremendous view of the lake, it was outstanding! We didn't expect the upgrade but the staff was so accommodating, what a delightful stay at Siebken's in Elkhart Lake, thank you!

Mary

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

The Harborview on Lake Michigan, an Ascend Collection Hotel

Port Washington

10/10 Excellent

Tammy

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

The Port Hotel

Port Washington

10/10 Excellent

This was our first visit to The Port Hotel and it certainly won't be the last! From the easy "no check-in desk" check-in through a very complete continental breakfast, this hotel is a true gem. Speaking of the "continental breakfast, the selections available rivaled or excelled many other hotel chains touting their "full" breakfast. The room was very clean and spacious. Bed linens were great and the bed itself was very comfortable. This property definitely deserves the "Best Hotel in Port...

Bill

Frequently Asked Questions

Can I find vacation rentals in Oostburg?

Yes, we offer vacation rentals near popular local attractions in Oostburg, or you can choose a more secluded option if you'd like a relaxing place to stay.

What's the top vacation rental in Oostburg?

Large Unique & Artistic Lake Michigan Beachfront House with Awesome Game Room: This Oostburg vacation home rental is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a private yard and a selection of games. Another good choice for your trip to Oostburg is Beautiful Remodeled Lake Michigan Beachfront Home, white sandy beach, 500Mpb int.

How many vacation rentals will I find in Oostburg?

With 21 Expedia vacation rentals, you're sure to find just the right place for your Oostburg stay.

What can I see and do in Oostburg?

Lake Michigan and Veteran's Park are a couple of scenic spots to enjoy the outdoors, whereas Whispering Pines Amphitheater is one of the cultural attractions. Kohler-Andrae State Park and Oostburg Public Library are other places to visit while you're in town.

What are vacation rentals like in Oostburg?

Vacation rentals are private accommodations you can stay in for several days or longer in Oostburg. Vacation rentals offer extras like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family trip or a small group gathering.

Oostburg Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oostburg vacation rentals

1. Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

2. Grandstay Residential Suites Hotel - Sheboygan

3. Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

4. Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

5. 3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

6. Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

7. Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

8. Sleeps 8 & Spacious!

9. The Beach town bungalow

10. Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

11. Logan Ave Holiday House - Upper

12. Beautiful & Convenient!

13. The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

14. Beachfront Paradise: King Suite - Sleeps 8!

15. Victorian Inn Elkhart Lake Wisconsin

16. Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

17. Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

18. The Links! - Luxury Golf Retreat with Golf Simulator

19. Just Beachy: 4 Bedroom, Sleeps 12!

20. Edgewater Villa: 4 Bedroom, Sleeps 14!

Find vacation rentals that suit your style

Top Oostburg Hotel Reviews

Fairfield Inn & Suites by Marriott Sheboygan

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Oostburg?

What's the top vacation rental in Oostburg?

How many vacation rentals will I find in Oostburg?

What can I see and do in Oostburg?

What are vacation rentals like in Oostburg?