Oostburg vacation rentals

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Top-rated vacation rentals in Oostburg

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

Apartment in Cedarburg

4.97 out of 5 average rating, 348 reviews

Cedarburg 2 br Apartment on prime Washington Ave

KelseyRating, 5 stars2 weeks ago

Kathy and Marty were very communicative. I knew without question if I needed anything they would answer right away. They were proactive with recommendations and directions for access. This is the second time I’ve stayed with them and will continue to do so any time I’m in Cedarburg! They are also close enough to Milwaukee for you to get multiple experiences if you are from out of town! Highly recommend a leisurely morning stroll to Boulangerie Du Monde and then Fiddleheads for coffee.

Guest favorite

Apartment in Port Washington

4.91 out of 5 average rating, 139 reviews

Lighthouse View -a real gem on Sweet Cake Hill

JohnRating, 5 stars1 week ago

Great hosts with a nice apartment, It was everything I remember about living in Port Washington. The older apartment made us feel right at home. Easy to find and within walking distance of downtown Port Washington. Thank you for providing our place to stay

Guest favorite

Home in Sheboygan

4.94 out of 5 average rating, 51 reviews

3-bdrm beachfront home on Lake Mich, Sheboygan WI

JohnRating, 5 stars6 months ago

Now that I have stayed at Jack's home @ 5 times, I can easily verify that every moment spent in that home is magical - steps away from a walk on the beach, the methodical waves lapping on the shoreline, and the majestic sunrises reflecting on the water combine to provide a therapeutic sensory experience that delivers 24 hours each day. If that isn't enough, there are fabulous coffee shops, restaurants, and bars that you can walk to as well as many others a short drive away. No - Jack does not pay me to write these reviews ... the reviews write themselves. Enjoy!

Guest favorite

Home in Oostburg

4.98 out of 5 average rating, 196 reviews

River Ridge-HOT TUB, Games, Luxury-10 bed, 5 STARS

JeremyRating, 5 stars5 days ago

Our stay at River Ridge was just what we were looking for. A relaxing stay with extra amenities to keep the family occupied. This hours has everything you need to be comfortable and is kept in amazing condition. Communication with Tyler and his management team was very simple and always very quick. We thoroughly enjoyed our stay!

Guest favorite

Home in Sheboygan

4.94 out of 5 average rating, 196 reviews

Beachfront getaway in Sheboygan

Laura KRating, 5 stars3 weeks ago

What a beautiful home! And a beautiful setting right on a sandy beach Lake Michigan. Plenty of board games and puzzles and music to listen to in the house. And we enjoyed trying local restaurants, all close by, and drove up to the dunes Park which was otherworldly and a short drive from the house.

Top guest favorite

Home in Oostburg

4.96 out of 5 average rating, 187 reviews

Shamba on the Lake, Oostburg, WI

SandyRating, 5 stars1 week ago

We have stayed at Shamba 4 times. It is an absolutely amazing spot on Lake Michigan. The home is lovely and very spacious. You could not ask for better views of the lake from inside or outside. The beach is literally right outside your door. Great spot for kids to play and great for walks too. Will definitely return again.

Guest favorite

Villa in Sheboygan

4.96 out of 5 average rating, 23 reviews

Perfect Paradise | 4BR Lakeview Condo w/ Jacuzzi

MikeRating, 5 stars6 months ago

Great host!! Great location!! Great property!! We came in town for a golf trip and this property was a perfect location and comfortable. Nice to start each morning with a quick walk to the beach and watch the sun rise over the lake. Would definitely stay here again and would recommend it to anyone looking to stay in the area.

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What guests are saying

A Glorious Getaway Sheboygan - LUX Lake Condo

4.98 out of 5 average rating, 41 reviews1 month ago

Susan was exceptionally responsive and inviting. She let us arrive early for our Mother's celebration of life weekend. It was easy to find once you figured out the address and unit numbers. Parking was ideal and plentiful. You can see the beach and lake from the walk out balcony.

Condo in Sheboygan

What guests are saying

Unmatched Location, Views, & Style. Welcome Home!

5 out of 5 average rating, 31 reviews1 week ago

This spacious and sublimely decorated, well-appointed, flat with gorgeous views of the Sheboygan River and Lake Michigan is immaculate, and each bedroom and bath is stocked with extra pillows, blankets, and fluffy towels. The furniture is comfortable, seems relatively new, and is not worn. Because we were due to arrive late on a very chilly night after a long flight and drive, I messaged Jill the morning of our scheduled arrival to let her know, and she made sure the place was heated and well lit when we arrived. There's very little for guests to do when checking out -Jill and crew make it easy.

Home in Sheboygan

What guests are saying

“On The Water” the Sheboygan River Overlook

4.94 out of 5 average rating, 18 reviews3 weeks ago

My husband, 8-year-old daughter, and I stayed at Dan’s place for two nights while in route to a tournament she was having that weekend. It was such a lovely stay. You don’t even need to leave the place. Our daughter just loved it and we felt right at home. Dan seems to go the extra mile- the towels were so soft, and the beds felt like clouds!

Home in Sheboygan Falls

What guests are saying

Woltring Waters Waterfront Home

4.9 out of 5 average rating, 72 reviews3 weeks ago

If you are in the general location of Lake Winnebago, I would highly suggest staying here! It had a lot of extra amenities that most places don't have and it was very relaxing and well located close to many things! I initially found great reasons to book Danielle's place because of the backyard and lake access which was definitely a hit for my girlfriend (she lives a block from the ocean) and also for me as it had a full kitchen, a large screen TV and also the ability for us to pack lighter due to the fact that there is a washer/dryer on site!

Home in Fond du Lac

What guests are saying

Heavenly Condo in the Malibu of the Midwest

4.97 out of 5 average rating, 31 reviews2 months ago

Debbie was super responsive from day 1 onward. Really enjoyed working with her for our 6-day stay. The place was nice and warm despite the sub-zero temps we had when there. Bed was comfortable and lots of hot water for showers. New appliances so meals in were easy. All in all a great place to stay. Thank you Debbie.

Condo in Sheboygan

What guests are saying

State Park w/ Orchard Style Yard & Pavilion

4.96 out of 5 average rating, 25 reviews7 months ago

We had a great stay at The Orchard House Retreat. The property is as described, looks like the pictures and had everything we needed. The kids especially loved all the toys and books! The house is 5 min to the State Park beach and 10 min from downtown. We loved having the backyard, the furniture was well taken care of and the fire pit was perfect for s’mores. The hosts were very responsive and accommodating— with everything labeled around the home. It’s also a great layout for bigger families /groups with 2 bedrooms upstairs, 1 on the main floor and 1 in the basement.

Home in Sheboygan

What guests are saying

Janelle's Dockside Condo

4.93 out of 5 average rating, 86 reviews2 weeks ago

We loved everything about this stay. Janelle has created a very beautiful space with absolutely everything we needed for a peaceful vacation. It is spacious and immaculately clean. The location is priceless. We had an easy walk to Lake Michigan, great restaurants, fun shops, and great coffee. We will definitely be back!

Condo in Sheboygan

What guests are saying

Spacious/stylish, 2br loft

4.98 out of 5 average rating, 96 reviews5 days ago

This was the perfect stay! Cynthia’s place is absolutely amazing—just as described. It’s a spacious, beautifully appointed loft in a great part of town. We were in town for an event at the John Michael Kohler Art Center, and everything planned for the weekend was just a few blocks away. We loved being able to walk everywhere and come home to such a gorgeous and comfortable space. Highly recommend!

Loft in Sheboygan

What guests are saying

Above Garage Apartment w/ Private Beach

4.94 out of 5 average rating, 54 reviews6 months ago

Dustin was a welcoming, kind host. He gave us the option of letting ourselves in or ringing the doorbell to meet him. We decided to meet him and had great conversation. We loved that he took the time to get to know us, even though he has a busy family. If we didn’t want to, we easily could have just walked up the stairs to the apartment with no contact, but meeting him made it more personal and memorable. Other notes: Dustin was very responsive and proactive. Prior to arrival, he messaged us, warning that there’s a dog (Stella) who would probably bark at us upon arrival. Indeed, she was there but was as sweet as can be and loved alllll the belly rubs. We had a busy weekend in the area, but we took a little time to explore the beautiful property. The apartment was just perfect and the best thing was that we didn’t have to do anything for checkout, except pack up our own things. We hope to visit again when we are up in that area in the future. Thank you, Dustin!

Guest suite in Waldo

What guests are saying

Luxury Retreat 1hr from Lambeau

4.98 out of 5 average rating, 40 reviews1 month ago

Amazing Stay – Impeccably Clean and Comfortable! I had an incredible stay at this home! From the moment I walked in, I was impressed by how spotless everything was. The space was not only beautiful but also meticulously cleaned, making it feel fresh and welcoming. The host clearly takes great care in maintaining the home, and it showed in every detail—from the crisp linens to the sparkling kitchen and bathroom. Beyond the cleanliness, the home was well-equipped with everything I needed for a comfortable stay. The bed was super cozy, and the atmosphere was peaceful, making it easy to relax. Communication with the host was seamless, and they were friendly and responsive. I highly recommend this place to anyone looking for a top-notch Airbnb experience. I would absolutely stay here again!

Villa in Plymouth

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Popular amenities for Oostburg vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Oostburg's top sights

Judi's Place9 locals recommend

Piggly Wiggly5 locals recommend

Oostburg Bakery3 locals recommend

Other great vacation rentals in Oostburg

Superhost

Cottage in Random Lake

4.84 out of 5 average rating, 67 reviews

Private 3 bedroom lake house

HoaRating, 5 stars1 week ago

Awesome place. We will be back!

Top guest favorite

Home in Hubertus

5 out of 5 average rating, 42 reviews

Cozy Cabin On Lake

CarloRating, 5 stars1 month ago

Just returned from the most amazing stay at the Cozy Cottage. It was an ideal break! Situated on Freiss Lake, the cottage is absolutely immaculate with wonderful attention to detail - every little thing has been considered and done to a high standard, to ensure you have a fantastic stay. It's been decorated in a rustic cabin style which beautifully compliments the space and setting. The place is just full of character and the beds are super comfortable. The other stand out is hosts, George and Noreen. They are warm, personable and nothing was too much trouble. They even made homemade chocolate chip cookies on my last night! So, stop reading reviews and go, this place is really special. Highly recommended!!!

Guest favorite

Farm stay in Germantown

4.97 out of 5 average rating, 98 reviews

Lace & Woods Farm "Hammer Hideaway"

RoryRating, 5 stars3 months ago

Such an enchanting stay. The hosts and resident animals were friendly. My family loved the barn cats that snuck their way to us - especially Carl. The wood fireplace added to the coziness. Everything was clean, comfortable, and heat moves well throughout the space. My mother-in-law is already planning our next visit come spring!

Superhost

Home in Sheboygan

4.77 out of 5 average rating, 13 reviews

3 Bedroom Beach House

KatieRating, 5 stars20 months ago

Place was great! Only comment I have is the beds were too soft (I need a firmer bed) :)

Top guest favorite

Home in Oostburg

5 out of 5 average rating, 11 reviews

SurfDaze! A Lake Michigan property

JosephRating, 5 stars1 month ago

We had an incredible stay at SurfDaze! The pictures don’t do it justice—this is a truly stunning beachfront property on Lake Michigan. The home was spotless, beautifully maintained, and exceptionally comfortable. Waking up to the sound of the waves and enjoying the breathtaking views made our trip unforgettable. We can’t wait to come back!

Superhost

Apartment in Sheboygan

4.5 out of 5 average rating, 12 reviews

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Christian DavidRating, 5 stars9 months ago

Excellent place, I was there for almost 2 months and is very peaceful, the place is exactly like photos, everything was great, Thank you Chris

Guest favorite

Home in Slinger

4.89 out of 5 average rating, 132 reviews

Aprés House - On the slopes of Little Switzerland

CarolinRating, 5 stars3 months ago

We absolutely loved our stay. This was our second time at this place! Great space, walking distance to Little Switz skiing, and enough space to host friends for dinner!

Top guest favorite