Oostburg, WI Vacation Homes from AED 620

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 vacation homes

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

Elisabeth D.

AED 620 total

includes taxes & fees

9 Nov - 10 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.

2. 3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

Sheboygan

Brian L.

AED 850 total

includes taxes & fees

27 Oct - 28 Oct

A dining table with a vase of green leaves and a candle.

3. Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Sheboygan

Stephanie M.

AED 792 total

includes taxes & fees

4 Nov - 5 Nov

A bedroom with a bed, a ceiling fan, a window with curtains, a view of the outdoors, and a small round table.

4. Sheboygan Riverside Condo

Sheboygan

Tressie J.

AED 1,025 total

includes taxes & fees

25 Oct - 26 Oct

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

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

Sheboygan

Anonymous traveler

AED 1,459 total

includes taxes & fees

25 Oct - 26 Oct

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

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

Sheboygan

Kristian N.

AED 2,264 total

includes taxes & fees

25 Oct - 26 Oct

A neatly made bed with a wooden headboard, a nightstand with a lamp, and a large mirror.

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

Sheboygan

Nicole B.

AED 1,259 total

includes taxes & fees

25 Oct - 26 Oct

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

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

Sheboygan

Nikki M.

AED 2,218 total

includes taxes & fees

25 Oct - 26 Oct

A modern kitchen with a central island, wooden cabinets, and a built-in stove. There is a dining area with a table and chairs, and a living room with a sofa and a fireplace.

9. Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.

Sheboygan

Brad T.

AED 3,498 total

includes taxes & fees

25 Oct - 26 Oct

A patio with a fire pit, outdoor seating, and string lights.

10. 3 Min to Road America, "Amazing Location!!"

Plymouth

Patrick F.

AED 3,251 total

includes taxes & fees

31 Oct - 1 Nov

A spacious living area with a modern staircase, a fireplace, and a flat-screen TV mounted on the wall.

11. Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

Plymouth

Cristy

AED 2,217 total

includes taxes & fees

1 Nov - 2 Nov

12. Modern Lakehouse w/ Hot Tub & Private Beach

Port Washington

"This property is truly amazing! Even though it was just my wife and I, this beautifully remodeled home is large enough to accommodate a large group and has a second kitchen in the lower level. The lake views are amazing from the hot tub on the deck, and it had a bon fire area set up as well. The host was very responsive to any questions we had and made the entire process seamless. The kitchen is absolutely incredible and was my favorite feature of the house...plus it was fully stocked...

matt a.

AED 2,121 total

includes taxes & fees

26 Oct - 27 Oct

A hotel room with two beds, a dining area, and a view of the outdoors.

13. Victorian Inn #241 | 2 Queen Beds

Elkhart Lake

AED 667 total

includes taxes & fees

25 Oct - 26 Oct

A deck with a hot tub, outdoor seating, and a view of a forested area.

14. Stunning private home hidden in the woods. Can sleep 11 guests

Plymouth

Nic B.

AED 3,542 total

includes taxes & fees

25 Oct - 26 Oct

A spacious kitchen with a brick accent wall, wooden cabinets, and a bar area with stools.

15. Home Port Vacation Escape

Port Washington

Linda M.

AED 1,995 total

includes taxes & fees

2 Nov - 3 Nov

An outdoor patio with a hot tub, string lights, and a covered seating area.

16. Immersed in Nature, Hot Tub, Sleeps 9, EV Charger

Cascade

Luke L.

AED 2,207 total

includes taxes & fees

18 Nov - 19 Nov

A grassy outdoor area with a wooden deck, a small shed, and a green hose coiled on the ground.

17. 5 min from Road America. Great yard and plenty of parking

Elkhart Lake

" We enjoyed our stay very much. The house is lovely, spacious, and clean. The property is quite big and provides an excellent space to walk or room for younger children to play. Several family members enjoyed a walk about after our drive on Saturday. The house was perfect for our group, and the living room was our gathering place for Saturday evening as well as Sunday morning. We cooked our evening meal and our morning breakfast in the kitchen. The only minor issue was that our group had 9...

Paul & Jacqleene M.

AED 3,725 total

includes taxes & fees

24 Oct - 25 Oct

A modern kitchen with a large island, bar stools, stainless steel appliances, and a view of a lake.

18. Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.

Campbellsport

"We had a great time at this property. The house was clean, spacious, well organized and the lake was beautiful. I am a new wheelchair user and this was my first vacation in two years so I was initially disappointed that there was a step down from the house to the large deck. My brother-in-law ended up driving back home to pick up a portable ramp that I use when I visit his house. That worked really well so if you are a wheelchair use be advised to bring or rent a ramp ahead of time if you want...

Amy T.

AED 9,738 total

includes taxes & fees

24 Oct - 25 Oct

A dining area with a table, chairs, and a window with curtains.

19. Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan

Sheboygan

AED 905 total

includes taxes & fees

9 Nov - 10 Nov

A spacious living area with a high ceiling, a wooden staircase, leather sofas, a flat-screen TV, and large windows.

20. Wisconsin Vacation Rental: 1 Mi to Road America!

Plymouth

Hiren T.

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Top Oostburg Hotel Reviews

The Oasis Hotel & Bar

10/10 Excellent

"Bar inside of hotel. Pool and hot tub, could not beat it!"

Large Unique & Artistic Lake Michigan Beachfront House with Awesome Game Room

10/10 Excellent

"A nice large home with amazing views of Lake Michigan and surrounding woods. The kitchen was well stocked for cooking and we didn't need to go out for meals. The design of the house is rather dated-an 80s contemporary with plenty of stairs. But very clean and neat and comfortable. One drawback was that the upper bedrooms got very hot and there didn't seem to be cold air coming out of the ac vents.The main level was very comfortable. Overall we had a great time and would definitely come back! The host was very responsive to any questions or concerns.house is a bit quirky, as the master bedroom is on 2 levels."

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oostburg vacation homes

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

2. 3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4