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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 59 Cottages in Sheboygan with updated reviews, rates, and availability.

BeachDaze a Lake Michigan Property
On the beach, sun loungers

BeachDaze a Lake Michigan Property

10.0 out of 10, Exceptional, (130)
"As always Cassie’s rentals are great. The house is cute and comfy with all we needed. The location being on Lake Michigan, is perfect for staying in and enjoying the fireplace on cold days, or walking along the beach. Plenty of parks nearby by for hikes and scenery. Visits to Port Washington and aSheboygan are minutes away with lots of great restaurants and things to do.Cassie is very prompt in replying to messages, and responded immediately when we managed to lock ouselves out one chilly...
BeachDaze a Lake Michigan Property
Peaceful Cottage on Lake Michigan
Property grounds

Peaceful Cottage on Lake Michigan

10.0 out of 10, Exceptional, (52)
"If only we hadn’t chose the coldest weekend this place is FANTASTIC! Cozy quiet and very nicely stocked with things to do. Host(s) are fantastic communicators! Highly recommend! "
Peaceful Cottage on Lake Michigan
3-bedroom cottage just 10 minutes from Kettle Moraine State Forest
Pool

3-bedroom cottage just 10 minutes from Kettle Moraine State Forest

10.0 out of 10, Exceptional, (33)
"Stay was excellent."
3-bedroom cottage just 10 minutes from Kettle Moraine State Forest
NEW! Shoreline Serenity
Fridge, microwave, oven, stovetop

NEW! Shoreline Serenity

10.0 out of 10, Exceptional, (1)
"This place is beautiful. It is decorated with a beachy theme that matches the breathtaking views. The attention to detail was superb and the little extras the owner added made our stay very special."
NEW! Shoreline Serenity
June dates available at SurfDaze!
Property grounds

June dates available at SurfDaze!

10.0 out of 10, Exceptional, (102)
"It was lovely and relaxing. "
June dates available at SurfDaze!
Cozy Lakefront Escape: Perfect for Seasonal Getaways & Large Groups
Fridge, microwave, oven, stovetop

Cozy Lakefront Escape: Perfect for Seasonal Getaways & Large Groups

2.5 star property
Cozy Lakefront Escape: Perfect for Seasonal Getaways & Large Groups
Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) )
Outdoor dining

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

10.0 out of 10, Exceptional, (165)
"Roomy enough for two adults, clean and well maintained property with a lake view and a dock right out the patio door. Perfect for summer time relaxing."
Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) )
A-frame on Horseshoe Lake
Smart TV

A-frame on Horseshoe Lake

10.0 out of 10, Exceptional, (81)
"Super fun property!"
A-frame on Horseshoe Lake
Private Beach, Outdoor Dining, Firepit
Property grounds

Private Beach, Outdoor Dining, Firepit

10.0 out of 10, Exceptional, (93)
"It is truly a special little cottage."
Private Beach, Outdoor Dining, Firepit
Bright and Cheerful Lake Front Beach Cottage
Beach

Bright and Cheerful Lake Front Beach Cottage

10.0 out of 10, Exceptional, (3)
"Adorable cottage with its own beach area!"
Bright and Cheerful Lake Front Beach Cottage
Lakeview cottage,88 ft to Lake Michigan, 2 bikes🚲
Exterior

Lakeview cottage,88 ft to Lake Michigan, 2 bikes🚲

10.0 out of 10, Exceptional, (12)
"Cute little house across from the beach. Perfect for biking and beaching."
Lakeview cottage,88 ft to Lake Michigan, 2 bikes🚲
East Shore Retreat
Outdoor dining

East Shore Retreat

East Shore Retreat
Pristine Beach Access, Arcade near Kohler-Andrae
Exterior

Pristine Beach Access, Arcade near Kohler-Andrae

10.0 out of 10, Exceptional, (12)
"Our annual canoe trip got rained out so we were so happy to find this spot! Hiked Kohler Andrae before checking in and had a great time playing ping pong and arcade games after the rain hit. Everything was great!"
Pristine Beach Access, Arcade near Kohler-Andrae
Lakefront Plymouth Cottage w/ Private Hot Tub
Terrace/patio

Lakefront Plymouth Cottage w/ Private Hot Tub

9.8 out of 10, Exceptional, (8)
"Great location near the track. Beautiful lake and fall color views."
Lakefront Plymouth Cottage w/ Private Hot Tub
No Cleaning Fee. King Bed. Cedar soaking Hot Tub, 5min walk to Beach
Indoor spa tub

No Cleaning Fee. King Bed. Cedar soaking Hot Tub, 5min walk to Beach

10.0 out of 10, Exceptional, (16)
"Absolutely beautiful we would highly recommend to anyone looking for a relaxing getaway"
The price is AED 716
AED 926 total
includes taxes & fees
19 May - 20 May
No Cleaning Fee. King Bed. Cedar soaking Hot Tub, 5min walk to Beach
Peaceful Lakefront Property ONLY 9.5 miles from Road America !
Outdoor dining

Peaceful Lakefront Property ONLY 9.5 miles from Road America !

10.0 out of 10, Exceptional, (4)
"We came to visit family and were so happy with our accomodations. The hosts are so friendly and the cabin felt like home. It all everything we needed and the beach access was a wonderful bonus!"
Peaceful Lakefront Property ONLY 9.5 miles from Road America !
Pet-friendly Sheboygan Home: 4 Mi to Lake Michigan
Property grounds

Pet-friendly Sheboygan Home: 4 Mi to Lake Michigan

3.0 star property
Pet-friendly Sheboygan Home: 4 Mi to Lake Michigan
Colorful Cottage w/ Hot Tub - Steps to Long Lake!
Microwave, dishwasher, coffee/tea maker, toaster

Colorful Cottage w/ Hot Tub - Steps to Long Lake!

9.4 out of 10, Exceptional, (3)
"Just what we wanted and expected."
Colorful Cottage w/ Hot Tub - Steps to Long Lake!
Family-friendly House: Walk to Lake Michigan!
Microwave, oven, stovetop, dishwasher

Family-friendly House: Walk to Lake Michigan!

3.0 star property
10.0 out of 10, Exceptional, (1)
Family-friendly House: Walk to Lake Michigan!
Dog-friendly Sheboygan Home - 1 Mi to Town!
House (1 Bedroom) | Private kitchen | Microwave, oven, stovetop, dishwasher

Dog-friendly Sheboygan Home - 1 Mi to Town!

3.0 star property
Dog-friendly Sheboygan Home - 1 Mi to Town!
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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Other property types in Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
Lobby

Grandstay Residential Suites Hotel - Sheboygan

2.5 star property
8.6 out of 10, Excellent, (914)
"Good place to stay"
The price is AED 446
AED 507 total
includes taxes & fees
27 May - 28 May
Grandstay Residential Suites Hotel - Sheboygan
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Outdoor dining

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

9.8 out of 10, Exceptional, (241)
"Perfect family getaway, very clean, cozy house & beautiful views! Mark is a great host, very accommodating and the property is very well maintained. Would definitely stay again! "
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
REMODELED HOME ON LAKE MICHIGAN
Property grounds

REMODELED HOME ON LAKE MICHIGAN

10.0 out of 10, Exceptional, (149)
"Easy check in, very clean."
REMODELED HOME ON 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.