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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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Oostburg holiday 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.

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Oostburg
10.0 out of 10, Exceptional, (146 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is NZ$306
includes taxes & fees
7 Oct - 8 Oct
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A spacious living area with a fireplace, a sofa, and a dining area in the background.

2. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,094 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is NZ$198
includes taxes & fees
29 Sept - 30 Sept
Grandstay Residential Suites Hotel - Sheboygan

3. 4 bed house on the shore of Lake Michigan

4 bed house on the shore of Lake Michigan
Belgium
9.4 out of 10, Exceptional, (81 reviews)
"The residence was spacious and well-maintained. The view of the lake from the living area is truly remarkable. The bed was comfortable."
United States
Danielle M.
The price is NZ$508
includes taxes & fees
6 Oct - 7 Oct
4 bed house on the shore of Lake Michigan
A fire pit surrounded by four light blue chairs in a grassy outdoor area.

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, (10 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$340
includes taxes & fees
6 Oct - 7 Oct
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
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.

5. 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, (31 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
The price is NZ$464
includes taxes & fees
4 Oct - 5 Oct
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
A bedroom with a wooden headboard, a bed with grey bedding, a fireplace, and a clock displaying 6:00.

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

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.6 out of 10, Exceptional, (33 reviews)
"The room was very clean and, as described. It was perfect for our weekend event. It was easy to communicate with the host."
United States
Kimberly H.
The price is NZ$230
includes taxes & fees
1 Oct - 2 Oct
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
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

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Sheboygan
10.0 out of 10, Exceptional, (7 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
6 Oct - 7 Oct
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
A dining table with a vase of green leaves and a candle.

8. 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 NZ$415
includes taxes & fees
6 Oct - 7 Oct
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
A modern living room with a grey sofa, a white armchair, a round coffee table, and a side table with a lamp.

9. Beautiful & Convenient!

Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (22 reviews)
"Place was clean and had everything we needed! "
United States
stormy a.
The price is NZ$583
includes taxes & fees
6 Oct - 7 Oct
Beautiful & Convenient!
A living room with a coffee station, a sofa, a ceiling fan, and a view of the outdoors.

10. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (30 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
The price is NZ$668
includes taxes & fees
6 Oct - 7 Oct
Sleeps 8 & Spacious!
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

11. 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 traveller
The price is NZ$740
includes taxes & fees
29 Sept - 30 Sept
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A two-story house with a front porch, a well-maintained lawn, and a sidewalk leading to the street.

12. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.4 out of 10, Exceptional, (9 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
The price is NZ$597
includes taxes & fees
20 Oct - 21 Oct
Logan Ave Holiday House - Upper
A laundry room with two front-loading washing machines, a shelf with cleaning supplies, and a green ironing board.

13. 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, (12 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
The price is NZ$340
includes taxes & fees
6 Oct - 7 Oct
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A dining area with a table, chairs, and a window with curtains.

14. 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 NZ$457
includes taxes & fees
29 Sept - 30 Sept
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
A brick building with a covered entrance, a Christmas tree, and a wreath.

15. Grace Adventure House, Family & Dog Friendly, Walk to Port, Shops, & the Beach!

Grace Adventure House, Family & Dog Friendly, Walk to Port, Shops, & the Beach!
Port Washington
10.0 out of 10, Exceptional, (29 reviews)
"Easy check in and check out!"
United States
Yvonne V.
The price is NZ$436
includes taxes & fees
29 Sept - 30 Sept
Grace Adventure House, Family & Dog Friendly, Walk to Port, Shops, & the Beach!
A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (14 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 Links! - Luxury Golf Retreat with Golf Simulator
A modern kitchen with a central island, a dining area with a coffee table, a sofa, and a TV mounted on the wall.

17. 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 NZ$532
includes taxes & fees
29 Sept - 30 Sept
Sheboygan Riverside Condo

18. Beachfront Paradise: King Suite - Sleeps 8!

Beachfront Paradise: King Suite - Sleeps 8!
Sheboygan
6.8 out of 10, (5 reviews)
"It was ok but it was the second year in a row that we did not get condo we rented due to a "door lock" issue."
United States
Nina S.
The price is NZ$1,129
includes taxes & fees
1 Oct - 2 Oct
Beachfront Paradise: King Suite - Sleeps 8!
A living room with a sofa, coffee table, and TV.

19. 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, (42 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is NZ$1,062
includes taxes & fees
29 Sept - 30 Sept
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
A stone building with a blue door, surrounded by a garden with blue flowers and a tree.

20. Be Still & Know, Luxury Historic Dog-friendly Apartment, Fireplace, Walk to Port

Be Still & Know, Luxury Historic Dog-friendly Apartment, Fireplace, Walk to Port
Port Washington
10.0 out of 10, Exceptional, (48 reviews)
"Everything was wonderful, clean and well presented. My girls and I, and the pup enjoyed our stay very much. "
United States
dj V.
The price is NZ$536
includes taxes & fees
30 Sept - 1 Oct
Be Still & Know, Luxury Historic Dog-friendly Apartment, Fireplace, Walk to Port
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

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

8/10 Good
"Really charming little room. Comfy, clean, full size fridge, a microwave, basic dishes. A person could easily stay here awhile. Perfect location to walk to the Kohler Art Center, dine at the Black Pig and even walk to the lighthouse! Would rate higher, but I was double billed...once by Expedia and again by the front desk at check in. I called about it once I was home and the front desk gal was pleasant, admitted there had been an error and will refund me accordingly. No issues in resolving."
Susan 1-night trip
Posted 2 hours ago
Grandstay Residential Suites Hotel - Sheboygan

Find out more about Oostburg

Everything you need to know about Oostburg holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oostburg holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oostburg holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oostburg holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oostburg. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oostburg holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oostburg holiday rentals we have selected for you start as low as NZ$198 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oostburg rentals

At Expedia, we put the best Oostburg holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oostburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oostburg holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oostburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.