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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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Oostburg vacation homes

A small, single-story house with a porch, surrounded by a gravel driveway and lush greenery.

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

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Oostburg
10.0 out of 10, Exceptional, (144 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is ￥24,578
￥29,495 total
includes taxes & fees
Oct 13 - Oct 14
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A dining table with a vase of green leaves and a candle.

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

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Sheboygan
10.0 out of 10, Exceptional, (8 reviews)
"The house was great! It had everything we needed, was very clean, and cozy. We enjoyed our stay and Ginger was welcoming, available, and responsive. "
United States
Christine P.
The price is ￥17,281
￥34,086 total
includes taxes & fees
Sep 21 - Sep 22
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
A wall with two framed paintings, a bench with cushions, and a light fixture.

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

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Sheboygan
The price is ￥27,650
￥45,679 total
includes taxes & fees
Oct 1 - Oct 2
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Sheboygan
10.0 out of 10, Exceptional, (42 reviews)
"Many extras that we have never seen at other rentals.Children's toys, beach toys, dog extras- leash dog bowls towels and a new toy to bring home. Walking distance to Lake Michigan. Restaurants that are 5 min distance driving. Kohler Andrae 15 min away! Kitchen had every item you would need.Hope to say again. Thanks for a great experience"
United States
Anonymous traveler
The price is ￥21,429
￥63,726 total
includes taxes & fees
Sep 21 - Sep 22
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A modern kitchen with a central island, stainless steel appliances, and a view to the outdoors.

5. Updated Plymouth Home ~ 5 Mi to Road America!

Updated Plymouth Home ~ 5 Mi to Road America!
Plymouth
10.0 out of 10, Exceptional, (19 reviews)
"This house was an excellent choice for our race weekend at Road America. It was very clean, the bedrooms were comfortable, check-in was easy, the neighborhood was quiet, and the proximity to the race track was great. Would definitely stay again!"
United States
Patricia V.
Updated Plymouth Home ~ 5 Mi to Road America!
A modern kitchen with a central island, a dining area with a coffee table, a sofa, and a TV mounted on the wall.

6. Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
10.0 out of 10, Exceptional, (2 reviews)
"Nice quiet place. Would stay again."
United States
Tressie J.
The price is ￥28,418
￥45,622 total
includes taxes & fees
Sep 15 - Sep 16
Sheboygan Riverside Condo
A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (13 reviews)
"Home was very clean and had everything we needed. Beds were comfortable. Easy to find and close to everything. "
United States
Andrea S.
The price is ￥34,562
￥94,671 total
includes taxes & fees
Sep 27 - Sep 28
The Links! - Luxury Golf Retreat with Golf Simulator
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

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Sheboygan
9.6 out of 10, Exceptional, (40 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is ￥48,387
￥88,570 total
includes taxes & fees
Sep 17 - Sep 18
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
A neatly made bed with a wooden headboard, a nightstand with a lamp, and a large mirror.

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

Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
Sheboygan
The price is ￥40,553
￥50,212 total
includes taxes & fees
Oct 1 - Oct 2
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
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.

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

Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
Sheboygan
10.0 out of 10, Exceptional, (17 reviews)
"Everything was clean and spacious. Had a great time and would definitely stay again! "
United States
Brad T.
The price is ￥67,435
￥137,212 total
includes taxes & fees
Sep 15 - Sep 16
Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
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

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Plymouth
9.8 out of 10, Exceptional, (17 reviews)
"Great property! Close to many great places. Property was very kid and adult friendly. Great time with family. We'll be back again. "
United States
Andrew M.
The price is ￥31,244
￥86,442 total
includes taxes & fees
Sep 15 - Sep 16
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
A cabin with a deck, a covered porch, and a paved driveway.

12. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (69 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
United States
Barbara
The price is ￥30,568
￥40,353 total
includes taxes & fees
Sep 15 - Sep 16
The Esker Ridge Chalet, Pristine Elkhart Solitude
A hotel room with two beds, a dining area, and a view of the outdoors.

13. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
The price is ￥14,670
￥26,805 total
includes taxes & fees
Sep 15 - Sep 16
Victorian Inn #241 | 2 Queen Beds
A patio with a fire pit, outdoor seating, and string lights.

14. 3 Min to Road America, "Amazing Location!!"

3 Min to Road America, "Amazing Location!!"
Plymouth
10.0 out of 10, Exceptional, (2 reviews)
"Beautifully appointed home. Perfect for family gathering or large group. Our family was pleasantly surprised with this gorgeous property!Host very accessable and reasonable."
United States
Kristine D.
The price is ￥60,215
￥127,217 total
includes taxes & fees
Sep 15 - Sep 16
3 Min to Road America, "Amazing Location!!"

15. Modern Lakehouse w/ Hot Tub & Private Beach

Modern Lakehouse w/ Hot Tub & Private Beach
Port Washington
The price is ￥90,968
￥109,423 total
includes taxes & fees
Oct 8 - Oct 9
Modern Lakehouse w/ Hot Tub & Private Beach
A deck with a hot tub, outdoor seating, and a view of a forested area.

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

Stunning private home hidden in the woods. Can sleep 11 guests
Plymouth
10.0 out of 10, Exceptional, (20 reviews)
"Our stay was great! Really enjoyed it!"
United States
Nic B.
The price is ￥122,888
￥141,478 total
includes taxes & fees
Sep 15 - Sep 16
Stunning private home hidden in the woods. Can sleep 11 guests
A spacious kitchen with a brick accent wall, wooden cabinets, and a bar area with stools.

17. Home Port Vacation Escape, Luxury Historic Home, Walk to Port, Beach, Shops

Home Port Vacation Escape, Luxury Historic Home, Walk to Port, Beach, Shops
Port Washington
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful home...great amenities and super communication from host!"
United States
Linda M.
The price is ￥40,977
￥92,536 total
includes taxes & fees
Oct 6 - Oct 7
Home Port Vacation Escape, Luxury Historic Home, Walk to Port, Beach, Shops
An outdoor patio with a hot tub, string lights, and a covered seating area.

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

Immersed in Nature, Hot Tub, Sleeps 9, EV Charger
Cascade
10.0 out of 10, Exceptional, (39 reviews)
"Great place for a lot of people to stay! Host was great! Hot tub was awesome. Very comfortable beds!! Will definitely be back."
United States
Luke L.
The price is ￥68,541
￥114,609 total
includes taxes & fees
Sep 28 - Sep 29
Immersed in Nature, Hot Tub, Sleeps 9, EV Charger
A grassy outdoor area with a wooden deck, a small shed, and a green hose coiled on the ground.

19. 5 min from Road America. Great yard and plenty of parking

5 min from Road America. Great yard and plenty of parking
Elkhart Lake
9.8 out of 10, Exceptional, (8 reviews)
" 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...
United States
Paul & Jacqleene M.
The price is ￥115,208
￥175,835 total
includes taxes & fees
Sep 26 - Sep 27
5 min from Road America. Great yard and plenty of parking
A modern kitchen with a large island, bar stools, stainless steel appliances, and a view of a lake.

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

Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.
Campbellsport
9.0 out of 10, Wonderful, (2 reviews)
"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...
United States
Amy T.
The price is ￥164,793
￥272,712 total
includes taxes & fees
Sep 20 - Sep 21
Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oostburg Hotel Reviews

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

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

10/10 Excellent
"Everything was great"
Travis M. 3-night trip
Posted 7 hours ago
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Find out more about Oostburg

Oostburg Vacation Homes information

Number of reviews
4,945
Accommodation
195 Vacation Homes
Lowest Price
￥10,753
Highest Price
￥174,347