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

Check prices for these dates

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

Our top choices for Oostburg vacation rentals

Exterior

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, (145 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
$164 nightly
The price is $173
Oct 19 - Oct 20
Total with taxes and fees
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Lobby

2. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,090 reviews)
"Nice place and good breakfast"
United States
Kristin
$133 nightly
The price is $151
Sep 28 - Sep 29
Total with taxes and fees
Grandstay Residential Suites Hotel - Sheboygan
Dining

3. 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.
$210 nightly
The price is $238
Oct 6 - Oct 7
Total with taxes and fees
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
3 bedrooms, desk, iron/ironing board, travel crib

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
$176 nightly
The price is $200
Oct 6 - Oct 7
Total with taxes and fees
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
1 bedroom, WiFi

5. 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.
$115 nightly
The price is $131
Oct 1 - Oct 2
Total with taxes and fees
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
On the beach

6. 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, (79 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.
$248 nightly
The price is $262
Sep 27 - Sep 28
Total with taxes and fees
4 bed house on the shore of Lake Michigan
Dining

7. 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.
$229 nightly
The price is $259
Sep 27 - Sep 28
Total with taxes and fees
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Smart TV, books

8. Close to Downtown & Shore | Great Location

Close to Downtown & Shore | Great Location
Sheboygan
9.0 out of 10, Wonderful, (10 reviews)
"Have stayed in all but one unit on this property and i must say, they are absolutely amazing!"
United States
Elizabeth S.
$280 nightly
The price is $317
Sep 23 - Sep 24
Total with taxes and fees
Close to Downtown & Shore | Great Location
Interior

9. 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.
$179 nightly
The price is $203
Sep 23 - Sep 24
Total with taxes and fees
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
3 bedrooms, desk, iron/ironing board, travel crib

10. Sleeps 7{SPACIOUS}Pets Welcome!

Sleeps 7{SPACIOUS}Pets Welcome!
Sheboygan
9.4 out of 10, Exceptional, (3 reviews)
"Great location and amenities. Would definitely book again!"
United States
Elizabeth S.
$331 nightly
The price is $376
Oct 6 - Oct 7
Total with taxes and fees
Sleeps 7{SPACIOUS}Pets Welcome!
Smart TV, books

11. 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.
$315 nightly
The price is $357
Oct 6 - Oct 7
Total with taxes and fees
Beautiful & Convenient!
Coffee/tea maker, fridge, microwave, stovetop

12. 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!
Interior

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.
$196 nightly
The price is $222
Oct 5 - Oct 6
Total with taxes and fees
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
House (3 Bedrooms) | Interior

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

Updated Plymouth Home ~ 5 Mi to Road America!
3.0 star property
Plymouth
10.0 out of 10, Exceptional, (3 reviews)
"Everything was great, very convenient to Road America."
United States
Kelis
Updated Plymouth Home ~ 5 Mi to Road America!
Interior

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

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Sheboygan
$222 nightly
The price is $252
Oct 6 - Oct 7
Total with taxes and fees
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Smart TV

16. 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.
$382 nightly
The price is $433
Sep 23 - Sep 24
Total with taxes and fees
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Exterior

17. 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
$323 nightly
The price is $367
Oct 21 - Oct 22
Total with taxes and fees
Logan Ave Holiday House - Upper
Coffee/tea maker, fridge, microwave, oven

18. 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.
$543 nightly
The price is $616
Sep 27 - Sep 28
Total with taxes and fees
The Links! - Luxury Golf Retreat with Golf Simulator
Coffee/tea maker, fridge, microwave, oven

19. 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
$366 nightly
The price is $415
Oct 21 - Oct 22
Total with taxes and fees
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Interior

20. 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.
$342 nightly
The price is $388
Oct 6 - Oct 7
Total with taxes and fees
Sleeps 8 & Spacious!
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

The Oasis Hotel & Bar

The Oasis Hotel & Bar

8/10 Good
"Great location for our visit. Clean room. No issues. Thank you."
Heidi 1-night trip
Posted 8 hours ago
The Oasis Hotel & Bar

Find out more about Oostburg

Everything you need to know about Oostburg vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oostburg vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oostburg vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oostburg in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $151 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oostburg rentals

At Expedia, we put the best Oostburg vacation 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 vacation.

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.

Explore a world of travel with Expedia

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: Visitors like this Oostburg vacation home rental. It 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 Tranquil Cottage in the Woods with Lake Michigan only 300 feet away..

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.