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
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Oostburg vacation rentals

Children's area

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, (139 reviews)
"Great little cottage. Perfect for a night away "
United States
James R.
The price is ￥25,184
￥30,389 total
includes taxes & fees
Sep 1 - Sep 2
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, (1,062 reviews)
"Great place to stay breakfast was good then room was good. Staff were great as well only issue is the pool is tiny."
United States
Devin
The price is ￥19,389
￥22,007 total
includes taxes & fees
Sep 1 - Sep 2
Grandstay Residential Suites Hotel - Sheboygan
House (2 Bedrooms) | Interior

3. Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
Sheboygan
The price is ￥28,489
￥65,118 total
includes taxes & fees
Aug 3 - Aug 4
Large Backyard, Walk to Hospital: Sheboygan Abode!
1 bedroom, WiFi

4. 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, (30 reviews)
"Communicative host, good location, comfortable and clean apartment. "
United States
Hannah T.
The price is ￥14,953
￥20,545 total
includes taxes & fees
Aug 17 - Aug 18
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Smart TV

5. 3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Sheboygan
9.8 out of 10, Exceptional, (18 reviews)
"Nice place, exactly as pictured. Enjoyed the coffee bar"
United States
Sylvia L.
The price is ￥26,601
￥46,629 total
includes taxes & fees
Aug 3 - Aug 4
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
TV

6. Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Great place to stay, the area is safe and close to the Marina. Owner/host was excellent to communicate with."
United States
Mary A.
The price is ￥21,564
￥66,459 total
includes taxes & fees
Aug 3 - Aug 4
Large Backyard, Walk to Hospital: Sheboygan Abode!
Terrace/patio

7. Stunning private home hidden in the woods. Can sleep 11 guests

Stunning private home hidden in the woods. Can sleep 11 guests
Plymouth
10.0 out of 10, Exceptional, (19 reviews)
"Our stay was great! Really enjoyed it!"
United States
Nic B.
The price is ￥125,920
￥151,776 total
includes taxes & fees
Aug 3 - Aug 4
Stunning private home hidden in the woods. Can sleep 11 guests
Exterior

8. Just Beachy: 4 Bedroom, Sleeps 12!

Just Beachy: 4 Bedroom, Sleeps 12!
Sheboygan
8.0 out of 10, Very Good, (6 reviews)
"The condo was very clean and comfortable. It was just steps from the lake. It's a great place to stay!"
United States
Erika M.
The price is ￥79,487
￥174,376 total
includes taxes & fees
Aug 3 - Aug 4
Just Beachy: 4 Bedroom, Sleeps 12!
Interior

9. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (28 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
The price is ￥20,322
￥62,368 total
includes taxes & fees
Aug 3 - Aug 4
Sleeps 8 & Spacious!
Smart TV, books

10. Beautiful & Convenient!

Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (21 reviews)
"Place was clean and had everything we needed! "
United States
stormy a.
The price is ￥19,434
￥55,466 total
includes taxes & fees
Aug 24 - Aug 25
Beautiful & Convenient!
Interior

11. 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, (6 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 ￥27,388
￥43,591 total
includes taxes & fees
Aug 25 - Aug 26
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Dining

12. 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, (7 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 ￥32,110
￥49,665 total
includes taxes & fees
Sep 1 - Sep 2
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Dining

13. 4 Bedroom Home on the River with Private River access

4 Bedroom Home on the River with Private River access
Sheboygan
9.8 out of 10, Exceptional, (43 reviews)
The price is ￥39,948
￥64,099 total
includes taxes & fees
Aug 13 - Aug 14
4 Bedroom Home on the River with Private River access
Golf

14. Luxury Home Historic location 4BR-3 FullBath- Walk 3 min beach, 10 to downtown

Luxury Home Historic location 4BR-3 FullBath- Walk 3 min beach, 10 to downtown
Sheboygan
9.8 out of 10, Exceptional, (40 reviews)
"We were very pleased with everything and would rent again if in the area."
United States
Amy K.
Luxury Home Historic location 4BR-3 FullBath- Walk 3 min beach, 10 to downtown
House (3 Bedrooms) | Interior

15. 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
The price is ￥30,378
￥62,521 total
includes taxes & fees
Aug 10 - Aug 11
Updated Plymouth Home ~ 5 Mi to Road America!
Coffee/tea maker, fridge, microwave, oven

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (10 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 price is ￥50,998
￥117,194 total
includes taxes & fees
Aug 4 - Aug 5
The Links! - Luxury Golf Retreat with Golf Simulator
Exterior

17. Be Still & Know, Luxury Apartment, Dog-friendly, Walk to Port, Shops, & Beach!

Be Still & Know, Luxury Apartment, Dog-friendly, Walk to Port, Shops, & Beach!
Port Washington
10.0 out of 10, Exceptional, (47 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 ￥28,746
￥58,712 total
includes taxes & fees
Aug 4 - Aug 5
Be Still & Know, Luxury Apartment, Dog-friendly, Walk to Port, Shops, & Beach!
Exterior

18. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.8 out of 10, Exceptional, (6 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
The price is ￥24,932
￥60,991 total
includes taxes & fees
Aug 5 - Aug 6
Logan Ave Holiday House - Upper
3 bedrooms, iron/ironing board, travel crib, WiFi

19. 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, (7 reviews)
"We enjoyed our stay and found the place very comfortable for our family of five. It was easy to walk down to see the lake and a quick drive to restaurants in town."
United States
Amanda
The price is ￥21,721
￥36,266 total
includes taxes & fees
Sep 1 - Sep 2
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Smart TV, books

20. Close to Downtown & Shore | Great Location

Close to Downtown & Shore | Great Location
Sheboygan
8.8 out of 10, Excellent, (8 reviews)
"Have stayed in all but one unit on this property and i must say, they are absolutely amazing!"
United States
Elizabeth S.
The price is ￥25,398
￥63,486 total
includes taxes & fees
Aug 9 - Aug 10
Close to Downtown & Shore | Great Location
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 Harborview on Lake Michigan, an Ascend Collection Hotel

The Harborview on Lake Michigan, an Ascend Collection Hotel

10/10 Excellent
"Na"
Ruth Anne 2-night trip
Posted 6 hours ago
The Harborview on Lake Michigan, an Ascend Collection Hotel

Find out more about Oostburg

Search for holiday rentals in Oostburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Oostburg using one of the methods below:

  • View our selection of featured holiday rentals in Oostburg
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Look no further and take a look at our great range of rental properties in Oostburg!

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?

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.: This Oostburg vacation home rental is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games. Another good choice for your trip to Oostburg is Large Unique & Artistic Lake Michigan Beachfront House with Awesome Game Room.

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.