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

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Oostburg vacation 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, (147 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
$160 nightly
The price is $169
Nov 9 - Nov 10
Total with taxes and fees
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, (1,105 reviews)
"Nice place and good breakfast"
United States
Kristin
$133 nightly
The price is $151
Nov 3 - Nov 4
Total with taxes and fees
Grandstay Residential Suites Hotel - Sheboygan
A bedroom with a wooden headboard, a bed with grey bedding, a fireplace, and a clock displaying 6:00.

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, (37 reviews)
"Very quiet, and only two blocks from Lake Michigan"
United States
Terri
$85 nightly
The price is $96
Oct 13 - Oct 14
Total with taxes and fees
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
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
$171 nightly
The price is $194
Oct 13 - Oct 14
Total with taxes and fees
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, (32 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
$230 nightly
The price is $261
Oct 14 - Oct 15
Total with taxes and fees
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
A bathroom with white shelves holding wicker baskets and a potted plant.

6. 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.
$181 nightly
The price is $205
Nov 10 - Nov 11
Total with taxes and fees
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.

7. 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.
$191 nightly
The price is $217
Oct 12 - Oct 13
Total with taxes and fees
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Living area

8. Come see Fall Colors in the Country and take up some hiking at local state parks

Come see Fall Colors in the Country and take up some hiking at local state parks
Waldo
10.0 out of 10, Exceptional, (7 reviews)
"Nice place to stay with family."
United States
Ann H.
$149 nightly
The price is $157
Oct 12 - Oct 13
Total with taxes and fees
Come see Fall Colors in the Country and take up some hiking at local state parks
A hotel room with a bed, a bedside table with a lamp, a small potted plant, and a window with curtains.

9. 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.
$307 nightly
The price is $348
Oct 12 - Oct 13
Total with taxes and fees
Sleeps 7{SPACIOUS}Pets Welcome!
A modern living room with a grey sofa, a white armchair, a round coffee table, and a side table with a lamp.

10. Beautiful & Convenient!

Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (22 reviews)
"Wonderful property! Communication was wonderful and so very helpful at all times. Not far from the marina, where we spent a lot of our time. "
United States
Susan G.
$297 nightly
The price is $337
Oct 12 - Oct 13
Total with taxes and fees
Beautiful & Convenient!
A laundry room with two front-loading washing machines, a shelf with cleaning supplies, and a green ironing board.

11. 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, (13 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
$170 nightly
The price is $193
Nov 8 - Nov 9
Total with taxes and fees
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A balcony with a wooden deck, a television on a wooden stand, and a fireplace.

12. Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!

Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
Sheboygan
10.0 out of 10, Exceptional, (17 reviews)
"Every detail was thought of and the host went out above and beyond to make it a memorable stay. "
United States
Melissa D.
$297 nightly
The price is $337
Nov 1 - Nov 2
Total with taxes and fees
Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
A two-story house with a front porch, a well-maintained lawn, and a sidewalk leading to the street.

13. 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
$299 nightly
The price is $339
Nov 11 - Nov 12
Total with taxes and fees
Logan Ave Holiday House - Upper
May 10, 2024

14. 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, (83 reviews)
"Location and privacy exceptional."
United States
michael g.
$370 nightly
The price is $390
Nov 2 - Nov 3
Total with taxes and fees
4 bed house on the shore of Lake Michigan
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

15. 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
$340 nightly
The price is $386
Nov 9 - Nov 10
Total with taxes and fees
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A deck with a view of a lake, surrounded by various signs and advertisements.

16. Victorian Inn Elkhart Lake Wisconsin

Victorian Inn Elkhart Lake Wisconsin
4.0 star property
Elkhart Lake
8.8 out of 10, Excellent, (3 reviews)
"Perfect location, great amenities."
United States
Deirdre
$644 nightly
The price is $706
Oct 12 - Oct 13
Total with taxes and fees
Victorian Inn Elkhart Lake Wisconsin
A living room with a coffee station, a sofa, a ceiling fan, and a view of the outdoors.

17. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (31 reviews)
"It suited our needs. Interior lighting was a bit harsh"
United States
James
$349 nightly
The price is $396
Nov 8 - Nov 9
Total with taxes and fees
Sleeps 8 & Spacious!
Beach

18. Beachfront Paradise: King Suite - Sleeps 8!

Beachfront Paradise: King Suite - Sleeps 8!
Sheboygan
7.0 out of 10, Good, (6 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.
$576 nightly
The price is $654
Oct 12 - Oct 13
Total with taxes and fees
Beachfront Paradise: King Suite - Sleeps 8!
A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (15 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
Oct 12 - Oct 13
Total with taxes and fees
The Links! - Luxury Golf Retreat with Golf Simulator
A stone building with two doors, numbered 426 and 427, and a bench outside.

20. Grace Adventure House, walk to Port, Lake Michigan

Grace Adventure House, walk to Port, Lake Michigan
Port Washington
10.0 out of 10, Exceptional, (30 reviews)
"Easy check in and check out!"
United States
Yvonne V.
$254 nightly
The price is $289
Oct 26 - Oct 27
Total with taxes and fees
Grace Adventure House, walk to Port, Lake Michigan
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

Inviting, Rustic Beach front cottage on Beautiful Lake Michigan

Inviting, Rustic Beach front cottage on Beautiful Lake Michigan

10/10 Excellent
"A great place for dogs! The fenced in deck is superb and lots of nice places to walk!"
Melody M. 4-night trip
Posted 2 days ago
Inviting, Rustic Beach front cottage on Beautiful Lake Michigan

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: This Oostburg vacation home rental 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.