Oostburg Holiday Rentals

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Our top choices for Oostburg holiday rentals

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, (116)
"We loved the cozy cottage and cuddled up with books under the afghans on the cool evenings. The lake was a pleasant walk away."
United States
bev w.
The price is AU$224
includes taxes & fees
5 Jan - 6 Jan 2026
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1010)
"Would definitely stay here again!"
United States
Donna
The price is AU$212
includes taxes & fees
17 Dec - 18 Dec
Grandstay Residential Suites Hotel - Sheboygan

Victorian Inn Elkhart Lake Wisconsin

Victorian Inn Elkhart Lake Wisconsin
4.0 star property
Elkhart Lake
8.8 out of 10, Excellent, (3)
"Perfect location, great amenities."
United States
Deirdre
Victorian Inn Elkhart Lake Wisconsin

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
10.0 out of 10, Exceptional, (1)
"In town for family celebration. This was a convenient location to my parent’s home! Thanks!"
United States
Shelly E.
The price is AU$259
includes taxes & fees
4 Jan - 5 Jan 2026
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

Upscale Waterfront and Pool View Condo!!

Upscale Waterfront and Pool View Condo!!
Elkhart Lake
10.0 out of 10, Exceptional, (4)
"We were in town for activities at Road America. The location of this villa is ideal and only a couple of miles from the track"
United States
Jason A.
The price is AU$668
includes taxes & fees
17 Dec - 18 Dec
Upscale Waterfront and Pool View Condo!!

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, (4)
"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 AU$259
includes taxes & fees
7 Jan - 8 Jan 2026
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
Sheboygan
The price is AU$603
includes taxes & fees
16 Dec - 17 Dec
Large Backyard, Walk to Hospital: Sheboygan Abode!

First Floor Pet Friendly Queen Suite with Single Pull-out

First Floor Pet Friendly Queen Suite with Single Pull-out
Elkhart Lake
10.0 out of 10, Exceptional, (2)
"So convenient to all things Elkhart Lake. Great accommodations and host. Would highly recommend!"
United States
Brenda H.
The price is AU$418
includes taxes & fees
14 Dec - 15 Dec
First Floor Pet Friendly Queen Suite with Single Pull-out

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, (6)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
United States
Stacy P.
The price is AU$289
includes taxes & fees
16 Dec - 17 Dec
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

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

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.8 out of 10, Exceptional, (24)
"Top notch, close to everything you want in Sheboygan "
United States
Cody
The price is AU$199
includes taxes & fees
20 Dec - 21 Dec
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

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

NEW Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
2.0 star property
Sheboygan
10.0 out of 10, Exceptional, (5)
The price is AU$411
includes taxes & fees
30 Dec - 31 Dec
NEW Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!

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
9.8 out of 10, Exceptional, (9)
"The flat is gorgeous and in a fantastic location. "
United States
Sarah G.
The price is AU$423
includes taxes & fees
24 Dec - 25 Dec
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.4 out of 10, Exceptional, (3)
"We had a great stay here during the boat races. The host was so nice and left us local cheese & beer to welcome us to the house/city. We would definitely stay here again!"
United States
MELISSA C.
The price is AU$475
includes taxes & fees
4 Jan - 5 Jan 2026
Logan Ave Holiday House - Upper

Modern Room Near Indoor Pool

Modern Room Near Indoor Pool
Elkhart Lake
9.6 out of 10, Exceptional, (4)
"Our host was extremely responsive and resourceful. The room was very clean and nice. "
United Kingdom
Brandon B.
The price is AU$418
includes taxes & fees
15 Dec - 16 Dec
Modern Room Near Indoor Pool

Sleeps 7{SPACIOUS}Pets Welcome!

Sleeps 7{SPACIOUS}Pets Welcome!
Sheboygan
9.4 out of 10, Exceptional, (3)
"Great location and amenities. Would definitely book again!"
United States
Elizabeth S.
Sleeps 7{SPACIOUS}Pets Welcome!

Waterfront Condo, Private Beach, Outdoor/Indoor Pools, & Walkable to Downtown

Waterfront Condo, Private Beach, Outdoor/Indoor Pools, & Walkable to Downtown
Elkhart Lake
10.0 out of 10, Exceptional, (8)
"Definitely recommend this unit and owner. "
United States
Patty M.
Waterfront Condo, Private Beach, Outdoor/Indoor Pools, & Walkable to Downtown

3 Min to Road America, outdoor deck, grill, & fire table

3 Min to Road America, outdoor deck, grill, & fire table
Plymouth
10.0 out of 10, Exceptional, (1)
"This place was perfect for our group. We were karting at Road America, and location was a little over a mile from the gate. Newly renovated and very nice. Hosts did lots of little things to add value to our stay. Plenty to do nearby. Kids loved the basement and yard, adults hung out on patio. Would definitely stay here again. "
United States
Matt W.
The price is AU$1,230
includes taxes & fees
12 Dec - 13 Dec
3 Min to Road America, outdoor deck, grill, & fire table

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
Sheboygan
9.8 out of 10, Exceptional, (12)
"It was an excellent place! Very comfortable, nice neighborhood, clean and exactly as described. We were very surprised and pleased with the welcome items left in the fridge! We Will definitely stay there again! "
United States
Kathy J.
The price is AU$560
includes taxes & fees
23 Dec - 24 Dec
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

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
10.0 out of 10, Exceptional, (21)
"Wonderfully close to the lake. Sad there was no off street parking."
United States
Lucas T.
The price is AU$604
includes taxes & fees
12 Dec - 13 Dec
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
2.0 star property
Ellis Historical District
9.6 out of 10, Exceptional, (12)
"A warm and cozy place to stay. Beautifully decorated and friendly hosts. Would stay again anytime we’re in Sheboygan."
United States
Rebecca S.
The price is AU$233
includes taxes & fees
20 Dec - 21 Dec
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
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

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 favourite 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 depend 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 AU$212 per night. Entering your travel dates in the search wizard might find you 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 Beach House / 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. Some other homes for rent in Oostburg include Tranquil Cottage in the Woods with Lake Michigan only 300 feet away. and Beautiful country home (3800 sq ft) on 4 acres with river frontage - 10 beds!.

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.