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 Holiday Rentals

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Our top choices for Oostburg holiday rentals

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, (151 reviews)
"Quiet place to just get away."
United States
Cheryl
The price is NZ$248
includes taxes & fees
16 Nov - 17 Nov
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

2. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,131 reviews)
"Was a very nice stay, hotel room was nice and staff was very helpful and friendly. Will definitely be coming back"
United States
Maxim
The price is NZ$213
includes taxes & fees
16 Nov - 17 Nov
Grandstay Residential Suites Hotel - Sheboygan

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

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.4 out of 10, Exceptional, (41 reviews)
"Very quiet, and only two blocks from Lake Michigan"
United States
Terri
The price is NZ$157
includes taxes & fees
18 Nov - 19 Nov
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

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

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Sheboygan
9.8 out of 10, Exceptional, (12 reviews)
"Close to everything we were looking to do while visiting the area. Great communication and hospitality from host, would stay again!!"
United States
Heidi
The price is NZ$302
includes taxes & fees
16 Nov - 17 Nov
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

3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Sheboygan
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stay and only a short walk to the beautiful beach."
United States
Brian L.
The price is NZ$349
includes taxes & fees
16 Nov - 17 Nov
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

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Sheboygan
9.4 out of 10, Exceptional, (15 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
The price is NZ$322
includes taxes & fees
18 Nov - 19 Nov
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

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Sheboygan
9.8 out of 10, Exceptional, (8 reviews)
"Very clean and good location; nice place for our dog; we would definitely stay again if the opportunity presents itself."
United States
Stephanie K.
The price is NZ$341
includes taxes & fees
15 Nov - 16 Nov
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

8. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (32 reviews)
"Great place in a great location for us."
United States
Dean M.
The price is NZ$675
includes taxes & fees
6 Dec - 7 Dec
Sleeps 8 & Spacious!

9. The Beach town bungalow

The Beach town bungalow
Sheboygan
The price is NZ$461
includes taxes & fees
14 Nov - 15 Nov
The Beach town bungalow

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

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Downtown Sheboygan
10.0 out of 10, Exceptional, (33 reviews)
"The location was perfect to experience the Art Fair, downtown, and the area overall!Clean & comfortable - would return!"
United States
Andrea L.
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

11. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.4 out of 10, Exceptional, (9 reviews)
"We had a great time up there and the host was excellent and the property was fantastic"
United States
Alex N.
The price is NZ$600
includes taxes & fees
13 Dec - 14 Dec
Logan Ave Holiday House - Upper

12. Beautiful & Convenient!

Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (23 reviews)
"The place was in a quiet neighborhood and a great location with easy access to everything we needed. Very clean and the host communicated everything clearly."
United States
Susan J.
The price is NZ$607
includes taxes & fees
18 Nov - 19 Nov
Beautiful & Convenient!

13. 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, (43 reviews)
"We absolutely loved our stay. Everything was so well stocked and comfortable. Perfect location near the lake. Between the fenced in yard for the dog and the little play area for the kids, it couldn’t have worked out better."
United States
Jean S.
The price is NZ$642
includes taxes & fees
15 Nov - 16 Nov
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

14. Beachfront Paradise: King Suite - Sleeps 8!

Beachfront Paradise: King Suite - Sleeps 8!
Sheboygan
7.0 out of 10, Good, (6 reviews)
"Property was clean and the check in process was smooth. Right on the beach which was fantastic!"
United States
Sherrill S.
The price is NZ$1,086
includes taxes & fees
14 Nov - 15 Nov
Beachfront Paradise: King Suite - Sleeps 8!

15. Victorian Inn Elkhart Lake Wisconsin

Victorian Inn Elkhart Lake Wisconsin
3.0 star property
Elkhart Lake
8.8 out of 10, Excellent, (3 reviews)
"Perfect location, great amenities."
United States
Deirdre
The price is NZ$1,028
includes taxes & fees
15 Nov - 16 Nov
Victorian Inn Elkhart Lake Wisconsin

16. 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
10.0 out of 10, Exceptional, (2 reviews)
"Very nice place. The owners were very helpful during our stay with recommendations on things to do as our fishing trip was cancelled!"
United States
Nicole B.
The price is NZ$580
includes taxes & fees
15 Nov - 16 Nov
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

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Sheboygan
9.8 out of 10, Exceptional, (43 reviews)
"Nice location and spacious."
United States
Maggie A.
The price is NZ$1,020
includes taxes & fees
15 Nov - 16 Nov
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (17 reviews)
"Perfect trip and great location"
United States
Kristian N.
The price is NZ$1,064
includes taxes & fees
15 Nov - 16 Nov
The Links! - Luxury Golf Retreat with Golf Simulator

19. Just Beachy: 4 Bedroom, Sleeps 12!

Just Beachy: 4 Bedroom, Sleeps 12!
Sheboygan
8.6 out of 10, Excellent, (8 reviews)
"The condo was very clean and comfortable. It was just steps from the lake. It's a great place to stay!"
United States
Erika M.
The price is NZ$1,390
includes taxes & fees
14 Nov - 15 Nov
Just Beachy: 4 Bedroom, Sleeps 12!

20. Edgewater Villa: 4 Bedroom, Sleeps 14!

Edgewater Villa: 4 Bedroom, Sleeps 14!
Sheboygan
8.2 out of 10, Very good, (18 reviews)
"Nice property, close to the beach. It was perfect for our weekend getaway. "
United States
Rebecca B.
The price is NZ$1,390
includes taxes & fees
14 Nov - 15 Nov
Edgewater Villa: 4 Bedroom, Sleeps 14!
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

Find out more about Oostburg

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oostburg holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oostburg. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oostburg. Seeing all the best attractions is bound to make you fall in love with Oostburg. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oostburg short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Oostburg?

Yes, there are holiday rentals close to the most popular sights in Oostburg, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oostburg has to offer?

Large Unique & Artistic Lake Michigan Beachfront House with Awesome Game Room: This highly rated holiday home rental in Oostburg is located on the beach, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a private garden and a selection of games. Another good choice for your trip to Oostburg is Tranquil Cottage in the Woods with Lake Michigan only 300 feet away..

How many holiday rentals will I find in Oostburg?

With 21 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Oostburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oostburg. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.