A wooden boardwalk along a sandy beach with dunes and a clear sky.

Holiday Rentals in Sheboygan County

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Our top choices for Sheboygan County holiday rentals

A spacious living area with a fireplace, a sofa, and a dining area in the background.

1. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,118 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is €122
includes taxes & fees
1 Nov - 2 Nov
Grandstay Residential Suites Hotel - Sheboygan
A spacious living area with a wooden dining table, chairs, and a sofa. There is a staircase leading to another level, and a large window providing natural light.

2. 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
10.0 out of 10, Exceptional, (33 reviews)
"The location was perfect to experience the Art Fair, downtown, and the area overall!Clean & comfortable - would return!"
United States
Andrea L.
The price is €276
includes taxes & fees
28 Oct - 29 Oct
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
A bedroom with a wooden headboard, a bed with grey bedding, a fireplace, and a clock displaying 6:00.

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

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.4 out of 10, Exceptional, (39 reviews)
"Very quiet, and only two blocks from Lake Michigan"
United States
Terri
The price is €90
includes taxes & fees
29 Oct - 30 Oct
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
A hallway leading to a room with a wooden floor, a white door, and a painting of sailboats on the wall.

4. 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
9.8 out of 10, Exceptional, (11 reviews)
"Close to everything we were looking to do while visiting the area. Great communication and hospitality from host, would stay again!!"
United States
Heidi
The price is €167
includes taxes & fees
28 Oct - 29 Oct
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
A living room with a coffee station, a sofa, a ceiling fan, and a view of the outdoors.

5. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (32 reviews)
"It suited our needs. Interior lighting was a bit harsh"
United States
James
The price is €333
includes taxes & fees
28 Oct - 29 Oct
Sleeps 8 & Spacious!
A modern living room with a grey sofa, a white armchair, a round coffee table, and a side table with a lamp.

6. Beautiful & Convenient!

Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (23 reviews)
"Wonderful property! Communication was wonderful and so very helpful at all times. Not far from the marina, where we spent a lot of our time. "
United States
Susan G.
The price is €333
includes taxes & fees
5 Nov - 6 Nov
Beautiful & Convenient!
A balcony with a wooden deck, a television on a wooden stand, and a fireplace.

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

Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
Sheboygan
10.0 out of 10, Exceptional, (18 reviews)
"Every detail was thought of and the host went out above and beyond to make it a memorable stay. "
United States
Melissa D.
The price is €280
includes taxes & fees
2 Nov - 3 Nov
Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

8. The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Sheboygan
10.0 out of 10, Exceptional, (43 reviews)
"We absolutely loved our stay. Everything was so well stocked and comfortable. Perfect location near the lake. Between the fenced in yard for the dog and the little play area for the kids, it couldn’t have worked out better."
United States
Jean S.
The price is €365
includes taxes & fees
16 Nov - 17 Nov
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A narrow hallway with a bench, pillows, and a potted plant.

9. Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Sheboygan
9.4 out of 10, Exceptional, (15 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
The price is €167
includes taxes & fees
28 Oct - 29 Oct
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

10. 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, (150 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is €185
includes taxes & fees
22 Nov - 23 Nov
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A two-story house with a front porch, a well-maintained lawn, and a sidewalk leading to the street.

11. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.4 out of 10, Exceptional, (9 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
The price is €283
includes taxes & fees
18 Nov - 19 Nov
Logan Ave Holiday House - Upper
A spacious living room with a sofa, armchairs, a coffee table, and a TV mounted on the wall. There is a dining area in the background with a table and chairs.

12. 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
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stay and only a short walk to the beautiful beach."
United States
Brian L.
The price is €212
includes taxes & fees
28 Oct - 29 Oct
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
A living room with a sofa, coffee table, and TV.

13. 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
9.8 out of 10, Exceptional, (43 reviews)
"Great place close to everything we needed. Walking distance to the coffee shop, beach, bar, and pizza place. Not much more you really need."
United States
Gregory D.
The price is €535
includes taxes & fees
31 Oct - 1 Nov
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
A modern kitchen with a central island, a dining area with a coffee table, a sofa, and a TV mounted on the wall.

14. Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
10.0 out of 10, Exceptional, (2 reviews)
"Nice quiet place. Would stay again."
United States
Tressie J.
Sheboygan Riverside Condo
A beach with pebbles, a wooden structure, and several birds.

15. Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
Sheboygan
10.0 out of 10, Exceptional, (2 reviews)
"Very nice place. The owners were very helpful during our stay with recommendations on things to do as our fishing trip was cancelled!"
United States
Nicole B.
The price is €305
includes taxes & fees
28 Oct - 29 Oct
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
A bathroom with white shelves holding wicker baskets and a potted plant.

16. 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
9.8 out of 10, Exceptional, (8 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 €178
includes taxes & fees
10 Nov - 11 Nov
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
A dining table with a vase of green leaves and a candle.

17. 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, (8 reviews)
"We stayed a very short time due to many wedding details and festivities and the stay was just what we needed. Convenient to wedding location, very clean, comfy beds, friendly and reliable host! Would highly recommend!"
United States
Stephanie M.
The price is €195
includes taxes & fees
1 Nov - 2 Nov
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
A modern kitchen with a central island, wooden cabinets, and a built-in stove. There is a dining area with a table and chairs, and a living room with a sofa and a fireplace.

18. Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.

Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
Sheboygan
10.0 out of 10, Exceptional, (17 reviews)
"Everything was clean and spacious. Had a great time and would definitely stay again! "
United States
Brad T.
The price is €872
includes taxes & fees
28 Oct - 29 Oct
Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
Exterior

19. Just Beachy: 4 Bedroom, Sleeps 12!

Just Beachy: 4 Bedroom, Sleeps 12!
Sheboygan
8.4 out of 10, Very good, (7 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 €734
includes taxes & fees
2 Nov - 3 Nov
Just Beachy: 4 Bedroom, Sleeps 12!
Beach

20. Beachfront Paradise: King Suite - Sleeps 8!

Beachfront Paradise: King Suite - Sleeps 8!
Sheboygan
7.0 out of 10, Good, (6 reviews)
"It was ok but it was the second year in a row that we did not get condo we rented due to a "door lock" issue."
United States
Nina S.
The price is €582
includes taxes & fees
29 Oct - 30 Oct
Beachfront Paradise: King Suite - Sleeps 8!
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 County Hotel Reviews

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

10/10 Excellent
"Quiet place near the lake."
Vivian 2-night trip
Posted 12 hours ago
Grandstay Residential Suites Hotel - Sheboygan

Find out more about Sheboygan County

Holiday Homes in Sheboygan County

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