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Featured Cottages in Sheboygan

Fall and Holiday dates still available at Beachdaze!

Fall and Holiday dates still available at Beachdaze!

Oostburg
With a stay at this cottage in Oostburg, you'll be on the beach, within a 10-minute drive of Lake Michigan and Oostburg Public Library.
Fall and Holiday dates still available at Beachdaze!
Lake Cottage pet friendly in Kettle Moraine Forest w/ Optional Boat Rental

Lake Cottage pet friendly in Kettle Moraine Forest w/ Optional Boat Rental

Campbellsport
Located in Campbellsport, this cottage is on the waterfront, a 1-minute drive from Kettle Moraine State Forest and 6 minutes from Spring Lake State Natural ...
Lake Cottage pet friendly in Kettle Moraine Forest w/ Optional Boat Rental
Fall and holiday dates still available at Surfdaze!

Fall and holiday dates still available at Surfdaze!

Oostburg
This cottage is 0.1 mi (0.1 km) from Lake Michigan and 2.6 mi (4.2 km) from Oostburg Public Library.
Fall and holiday dates still available at Surfdaze!
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NEW! Lakeview Cottage on 3.5 acres w/hot tub and fire pit

NEW! Lakeview Cottage on 3.5 acres w/hot tub and fire pit

Cleveland
When you stay at this cottage in Cleveland, you'll be next to a golf course, just steps from Lake Michigan and a 3-minute drive from Hika Bay.
NEW! Lakeview Cottage on 3.5 acres w/hot tub and fire pit
A-frame on Horseshoe Lake

A-frame on Horseshoe Lake

Newton
Located in Newton, this cottage is on the waterfront, within a 15-minute drive of Esch Library and Dairyland Park.
A-frame on Horseshoe Lake
Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) )

Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) )

Kiel
Located in Kiel, this cottage is on a lake, within a 15-minute drive of Wilke Lake and Vanderbloemen Bog State Natural Area.
Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) )
The Pond Cottage - Lake Front on Beautiful Lake Michigan

The Pond Cottage - Lake Front on Beautiful Lake Michigan

Oostburg
This beach cottage is 0.1 mi (0.1 km) from Lake Michigan and 3.2 mi (5.2 km) from Oostburg Public Library.
The Pond Cottage - Lake Front on Beautiful Lake Michigan
Pristine Beach Access, Arcade near Kohler-Andrae

Pristine Beach Access, Arcade near Kohler-Andrae

Oostburg
With a stay at this cottage in Oostburg, you'll be near the beach, within a 15-minute drive of Lake Michigan and Whispering Pines Amphitheater.
Pristine Beach Access, Arcade near Kohler-Andrae
Lakefront Plymouth Cottage w/ Private Hot Tub

Lakefront Plymouth Cottage w/ Private Hot Tub

Plymouth
Located in Plymouth, this cottage is a 4-minute drive from Skip Barber Driving School and 5 minutes from Farmers Market.
Lakefront Plymouth Cottage w/ Private Hot Tub
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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.

Sheboygan Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Sheboygan will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Sheboygan definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Sheboygan, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Sheboygan Cottages essential information

Accommodation
50 Cottages
Lowest Price
AU$148
Highest Price
AU$297
Popular accommodation
Fall and Holiday dates still available at Beachdaze! , Lake Cottage pet friendly in Kettle Moraine Forest w/ Optional Boat Rental, Fall and holiday dates still available at Surfdaze! , NEW! Lakeview Cottage on 3.5 acres w/hot tub and fire pit, A-frame on Horseshoe Lake , Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) ), The Pond Cottage - Lake Front on Beautiful Lake Michigan, Pristine Beach Access, Arcade near Kohler-Andrae, Lakefront Plymouth Cottage w/ Private Hot Tub

Top trending hotels in Sheboygan

AmericInn by Wyndham Sheboygan

AmericInn by Wyndham Sheboygan

2 out of 5
3664 S Taylor Dr, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is AU$148 per night from 29 Nov to 30 Nov
AU$148
includes taxes & fees
29 Nov - 30 Nov
With a stay at AmericInn by Wyndham Sheboygan in Sheboygan, you'll be in a shopping district, within a 10-minute drive of Lake Michigan and Deer Trace Mall.
AmericInn by Wyndham Sheboygan
La Quinta Inn by Wyndham Sheboygan

La Quinta Inn by Wyndham Sheboygan

2.5 out of 5
2932 Kohler Memorial Dr, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 24 Nov to 25 Nov
AU$149
includes taxes & fees
24 Nov - 25 Nov
With a stay at La Quinta Inn by Wyndham Sheboygan in Sheboygan, you'll be next to a golf course, within a 10-minute drive of Lake Michigan and HSHS St. Nicholas ...
La Quinta Inn by Wyndham Sheboygan
Blue Harbor Resort and Conference Center

Blue Harbor Resort and Conference Center

3 out of 5
725 Blue Harbor Drive, Sheboygan, WI
The price is AU$297 per night from 24 Nov to 25 Nov
AU$297
includes taxes & fees
24 Nov - 25 Nov
When you stay at Blue Harbor Resort and Conference Center in Sheboygan, you'll be on the beach, within a 5-minute drive of Stefanie H. Weill Center for the Performing ...
Blue Harbor Resort and Conference Center
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Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

2.5 out of 5
708 Niagara Avenue, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is AU$190 per night from 24 Nov to 25 Nov
AU$190
includes taxes & fees
24 Nov - 25 Nov
With a stay at Grandstay Residential Suites Hotel - Sheboygan in Sheboygan (Downtown Sheboygan), you'll be within a 15-minute walk of Lake Michigan and Above ...
Grandstay Residential Suites Hotel - Sheboygan
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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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^Subject to availability and chosen travel dates.