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Sheboygan Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Sheboygan vacation rentals

Lobby

1. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,070 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 AED 450
AED 511 total
includes taxes & fees
1 Sep - 2 Sep
Grandstay Residential Suites Hotel - Sheboygan
1 bedroom, WiFi

2. 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 AED 349
AED 479 total
includes taxes & fees
18 Aug - 19 Aug
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Dining

3. 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, (24 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
The price is AED 411
AED 1,013 total
includes taxes & fees
15 Sep - 16 Sep
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Interior

4. 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 AED 412
AED 1,385 total
includes taxes & fees
19 Aug - 20 Aug
Sleeps 8 & Spacious!
3 bedrooms, iron/ironing board, travel crib, WiFi

5. 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, (9 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 AED 463
AED 792 total
includes taxes & fees
1 Sep - 2 Sep
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Smart TV

6. 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.
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Smart TV, books

7. 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 AED 404
AED 1,234 total
includes taxes & fees
31 Aug - 1 Sep
Beautiful & Convenient!
Children's area

8. 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, (140 reviews)
"Great little cottage. Perfect for a night away "
United States
James R.
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Interior

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, (12 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
The price is AED 476
AED 811 total
includes taxes & fees
24 Aug - 25 Aug
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Exterior

10. 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 AED 525
AED 1,351 total
includes taxes & fees
2 Sep - 3 Sep
Logan Ave Holiday House - Upper
House (2 Bedrooms) | Interior

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

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
Sheboygan
The price is AED 665
AED 1,520 total
includes taxes & fees
17 Aug - 18 Aug
Large Backyard, Walk to Hospital: Sheboygan Abode!
Smart TV

12. 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, (34 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is AED 661
AED 1,572 total
includes taxes & fees
17 Aug - 18 Aug
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
TV

13. 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.
Large Backyard, Walk to Hospital: Sheboygan Abode!
Interior

14. 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 AED 573
AED 934 total
includes taxes & fees
19 Aug - 20 Aug
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Dining

15. 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)
"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 AED 617
AED 992 total
includes taxes & fees
14 Sep - 15 Sep
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
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, (11 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 Links! - Luxury Golf Retreat with Golf Simulator
Exterior

17. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (65 reviews)
"What a perfect getaway and the host was very accommodating while respecting our privacy. We would definitely recommend!!!"
United States
Brycie K.
The price is AED 731
AED 1,011 total
includes taxes & fees
18 Aug - 19 Aug
The Esker Ridge Chalet, Pristine Elkhart Solitude
Coffee/tea maker, fridge, microwave, stovetop

18. Updated Plymouth Home ~ 5 Mi to Road America!

Updated Plymouth Home ~ 5 Mi to Road America!
Plymouth
10.0 out of 10, Exceptional, (19 reviews)
"This house was an excellent choice for our race weekend at Road America. It was very clean, the bedrooms were comfortable, check-in was easy, the neighborhood was quiet, and the proximity to the race track was great. Would definitely stay again!"
United States
Patricia V.
Updated Plymouth Home ~ 5 Mi to Road America!
Interior

19. Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Nice quiet place. Would stay again."
United States
Tressie J.
Sheboygan Riverside Condo
Iron/ironing board, WiFi, bed sheets

20. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
The price is AED 417
AED 724 total
includes taxes & fees
17 Aug - 18 Aug
Victorian Inn #241 | 2 Queen Beds
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

Fairfield Inn & Suites by Marriott Sheboygan

Fairfield Inn & Suites by Marriott Sheboygan

10/10 Excellent
"Clean room, and price was decent"
Kari 1-night trip
Posted 4 hours ago
Fairfield Inn & Suites by Marriott Sheboygan

Frequently asked questions

Can I find a vacation rental in Sheboygan?

Yes, we offer vacation rentals in Sheboygan close to John Michael Kohler Arts Center, or you can go with a more remote option if you want a relaxing stay. Visitors to Sheboygan speak positively about the scenic lakeside and top-notch restaurants in this destination. Leave some time to check out the marina and museums during your trip.

What are some of the best vacation home rentals in Sheboygan?

REMODELED HOME ON LAKE MICHIGAN: This Sheboygan vacation home rental is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind. Our travelers also rate Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host! as a favorite home for rent in Sheboygan.

How many vacation rentals will I find in Sheboygan?

Choose from 94 Expedia vacation rentals in Sheboygan for a memorable vacation.

What’s there to see and do in Sheboygan?

Enjoy the outdoors at Lake Michigan and North Side Municipal Beach, or simply take in cultural attractions like John Michael Kohler Arts Center and Sheboygan County Historical Museum. While here, Blue Harbor Resort & Conference Center Water Park and Bookworm Gardens are other places worth a visit.

What’s a vacation rental in Sheboygan like?

A vacation rental is a private property where you can stay for a long or short time in Sheboygan. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family getaway.