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Check prices for these dates

Next weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Sheboygan Cottages

NEW! Shoreline Serenity
Enjoy meals and socialize in this kitchen with a central island, ample cabinetry, and ocean views.

NEW! Shoreline Serenity

9.8 out of 10, Exceptional, (9)
"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
Fall dates available at SurfDaze!
Enjoy unobstructed views of the water from this outdoor seating area.

Fall dates available at SurfDaze!

10.0 out of 10, Exceptional, (104)
"We've been going to this area of Michigan beach for several years as a spring experience and this is our favorite lakefront vrbo. "
Fall dates available at SurfDaze!
On The Rocks. Lake Michigan Beachfront Home.
On the beach, sun loungers, beach towels

On The Rocks. Lake Michigan Beachfront Home.

9.8 out of 10, Exceptional, (7)
On The Rocks. Lake Michigan Beachfront Home.
3-bedroom lake cottage in the Kettle Moraine State Forest
Staircase ascends through a lush park setting surrounded by trees and greenery.

3-bedroom lake cottage in the Kettle Moraine State Forest

9.8 out of 10, Exceptional, (40)
"Stay was excellent."
3-bedroom lake cottage in the Kettle Moraine State Forest
A-frame on Horseshoe Lake
Cozy cabin-style room with a dining area, fireplace, and large windows.

A-frame on Horseshoe Lake

10.0 out of 10, Exceptional, (88)
"Super fun property!"
A-frame on Horseshoe Lake
East Shore Retreat
Enjoy a peaceful evening on the patio with a fire pit and breathtaking views of the water.

East Shore Retreat

6.0 out of 10, (1)
"Beautiful view and main room. Dishes were dir"
East Shore Retreat
Fall dates and holidays available!
Enjoy the tranquil ocean views from this elevated platform overlooking the beach.

Fall dates and holidays available!

10.0 out of 10, Exceptional, (133)
"My husband and I stayed here for a weekend to celebrate my birthday, and as soon as we got there we wanted to extend our stay! This is a wonderfully clean and well cared for home that had everything we needed. The views were amazing, and the fireplace was perfect for a cold March evening. Listening the waves and reading a book were just what we needed for a relaxing weekend. We hadn't left before we started looking into the listing to book our next trip to BeachDaze!"
Fall dates and holidays available!
Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) )
Relax in a serene backyard oasis with a deck, lush greenery, and a well-manicured lawn.

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

10.0 out of 10, Exceptional, (176)
"We experienced a death in the family. The cottage was quiet and healing. I loved being able to look at the lake and hear the ducks. "
Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) )
Peaceful Cottage on Lake Michigan
Relax by the ocean with a serene view, a picnic table, and benches surrounded by tall trees.

Peaceful Cottage on Lake Michigan

10.0 out of 10, Exceptional, (59)
"We loved our stay and were sad to leave. Location was great and the cottage had everything we needed and then some. Would definitely stay again!"
Peaceful Cottage on Lake Michigan
Peaceful Lakefront Property ONLY 9.5 miles from Road America !
Cozy cabin-style retreat with a charming porch and comfortable seating area.

Peaceful Lakefront Property ONLY 9.5 miles from Road America !

10.0 out of 10, Exceptional, (5)
"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 !
Private Beach, Outdoor Dining, Firepit
Relax in Adirondack chairs facing the ocean, with a fire pit at the center.

Private Beach, Outdoor Dining, Firepit

10.0 out of 10, Exceptional, (102)
"It is truly a special little cottage."
Private Beach, Outdoor Dining, Firepit
Cozy Lakefront Escape: Perfect for Seasonal Getaways & Large Groups
Enjoy cooking in this well-equipped kitchen with a central island, ample counter space, and integrated appliances.

Cozy Lakefront Escape: Perfect for Seasonal Getaways & Large Groups

2.5 star property
10.0 out of 10, Exceptional, (1)
"It’s a cute place with comfortable beds, clean linens, and plenty of seating. There are lots of windows in the downstairs and the view is great. There are four bedrooms upstairs, and a separate loft area over the garage with the other beds. It’s a great place and will be going back!"
Cozy Lakefront Escape: Perfect for Seasonal Getaways & Large Groups
See the Lake! Hear the Waves! Steps to the Beach! Entire cottage. 2 bikes.
Shopko Gate entrance leads to a retail space within the stadium, offering a convenient shopping experience.

See the Lake! Hear the Waves! Steps to the Beach! Entire cottage. 2 bikes.

10.0 out of 10, Exceptional, (13)
"Cute little house across from the beach. Perfect for biking and beaching."
See the Lake! Hear the Waves! Steps to the Beach! Entire cottage. 2 bikes.
Updated Plymouth Home ~ 5 Mi to Road America!
Relax in a spacious living room with a large window offering a view of the outdoors, a flat-screen TV, and a comfortable seating area.

Updated Plymouth Home ~ 5 Mi to Road America!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful spot, calm and clean neighborhood, close to the track. A real find."
Updated Plymouth Home ~ 5 Mi to Road America!
Steps to Lake Michigan: Manitowoc Home w/ Fire Pit
Enjoy cooking in this well-lit kitchen with sleek cabinetry, a dishwasher, and oven.

Steps to Lake Michigan: Manitowoc Home w/ Fire Pit

3.0 star property
Steps to Lake Michigan: Manitowoc Home w/ Fire Pit
Spacious Recently Built Home < 1 Mi to Lake!
Enjoy meals in this serene dining area with a view of the surrounding landscape.

Spacious Recently Built Home < 1 Mi to Lake!

3.0 star property
Spacious Recently Built Home < 1 Mi to Lake!
Lakefront Plymouth Cottage w/ Private Hot Tub
Relax on the deck overlooking the serene lake with a tranquil view of boats.

Lakefront Plymouth Cottage w/ Private Hot Tub

3.0 star property
Lakefront Plymouth Cottage w/ Private Hot Tub
Riverfront Two Rivers Vacation Rental By Beaches
House (2 Bedrooms) | Interior

Riverfront Two Rivers Vacation Rental By Beaches

3.0 star property
8.0 out of 10, Very good, (1)
"Overall, a very nice property. Updated amenities, comfortable space and right on the river, which was great. Two small frustrations - there were no toiletries in the house (body wash, shampoo, etc) which we have come to expect with rental properties like this. We had to go and buy our own. Second, there were quite a few flies in the house when we got there. We were able to get rid of them but it was a bit of a hassle. "
Riverfront Two Rivers Vacation Rental By Beaches
Family-friendly House: Walk to Lake Michigan!
Enjoy cooking in this well-equipped kitchen with a refrigerator, dishwasher, and countertop.

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!
Pet-friendly Sheboygan Home, 1 Mi to Lake Michigan
House (4 Bedrooms) | Interior

Pet-friendly Sheboygan Home, 1 Mi to Lake Michigan

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a great stay. This is a very nice home. BEAUTIFUL home. Would recommend. Only complaint was lack of electrical outlets. I would recommend and electrician come in and upgrade the home just a bit. OTHER WISE THIS PLACE IS AMAZING WITH TONS OF ROOM!"
Pet-friendly Sheboygan Home, 1 Mi to 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.
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Top Sheboygan Hotel Reviews

Watershed Hotel

Watershed Hotel

10/10 Excellent
"Excellent hotel. Very clean. Friendly and welcoming staff at check-in. I would highly recommend. The rooms are clean, modern, and esthetically pleasing. "
Jon 1-night trip
Posted 2 days ago
Watershed Hotel