Sheboygan Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Sheboygan vacation homes
1. 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 4Sheboygan
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stay and only a short walk to the beautiful beach."
Brian L.
The price is CA $141
CA $278 total
includes taxes & fees
Nov 16 - Nov 17
2. Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire PitSheboygan
10.0 out of 10, Exceptional, (10 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!"
Stephanie M.
The price is CA $168
CA $311 total
includes taxes & fees
Nov 15 - Nov 16
3. 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, (151 reviews)
"Quiet place to just get away."
Cheryl
The price is CA $180
CA $197 total
includes taxes & fees
Nov 16 - Nov 17
4. The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully FencedSheboygan
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."
Jean S.
The price is CA $160
CA $514 total
includes taxes & fees
Dec 6 - Dec 7
5. Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Eclectic Artsy 3-bedroom house with King Bed & AC in SheboyganSheboygan
10.0 out of 10, Exceptional, (1 review)
"Great location, centrally located, clean and well-furnished. Ginger was a great host, very accommodating."
Tonja K.
The price is CA $167
CA $309 total
includes taxes & fees
Nov 15 - Nov 16
6. Victorian Inn #241 | 2 Queen Beds
Victorian Inn #241 | 2 Queen BedsElkhart Lake
The price is CA $145
CA $246 total
includes taxes & fees
Nov 22 - Nov 23
7. Beachfront Paradise: King Suite - Sleeps 8!
Beachfront Paradise: King Suite - Sleeps 8!Sheboygan
7.0 out of 10, Good, (6 reviews)
"Property was clean and the check in process was smooth. Right on the beach which was fantastic!"
Sherrill S.
The price is CA $278
CA $886 total
includes taxes & fees
Nov 15 - Nov 16
8. The Esker Ridge Chalet, Pristine Elkhart Solitude
The Esker Ridge Chalet, Pristine Elkhart SolitudeElkhart Lake
10.0 out of 10, Exceptional, (73 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
Barbara
The price is CA $321
CA $431 total
includes taxes & fees
Nov 17 - Nov 18
9. 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 citySheboygan
9.8 out of 10, Exceptional, (43 reviews)
"Nice location and spacious."
Maggie A.
The price is CA $449
CA $780 total
includes taxes & fees
Nov 22 - Nov 23
10. 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 ChairSheboygan
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!"
Nicole B.
The price is CA $377
CA $465 total
includes taxes & fees
Nov 15 - Nov 16
11. The Links! - Luxury Golf Retreat with Golf Simulator
The Links! - Luxury Golf Retreat with Golf SimulatorSheboygan
10.0 out of 10, Exceptional, (17 reviews)
"Perfect trip and great location"
Kristian N.
The price is CA $336
CA $854 total
includes taxes & fees
Nov 15 - Nov 16
12. New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!Two Rivers
10.0 out of 10, Exceptional, (50 reviews)
"So delightful and a wonderful stay!"
Tom & Jenny S.
The price is CA $141
CA $332 total
includes taxes & fees
Nov 22 - Nov 23
13. Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road AmericaReedsville
9.8 out of 10, Exceptional, (36 reviews)
"Our 4th time here. Great stay as always."
Jason R.
The price is CA $428
CA $655 total
includes taxes & fees
Nov 17 - Nov 18
14. Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable PlymouthPlymouth
9.8 out of 10, Exceptional, (19 reviews)
"Everything was amazing and if we come back next year we will be staying again"
Cristy
The price is CA $286
CA $794 total
includes taxes & fees
Nov 17 - Nov 18
15. 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, (18 reviews)
"Everything was clean and spacious. Had a great time and would definitely stay again! "
Brad T.
The price is CA $818
CA $1,448 total
includes taxes & fees
Nov 15 - Nov 16
16. 1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!Two Rivers
9.6 out of 10, Exceptional, (15 reviews)
"Great place for book club"
Kelly S.
The price is CA $211
CA $787 total
includes taxes & fees
Nov 17 - Nov 18
17. Road America, Elkhart Lake!
Road America, Elkhart Lake!Elkhart Lake
7.0 out of 10, Good, (2 reviews)
The price is CA $267
CA $524 total
includes taxes & fees
Dec 8 - Dec 9
18. Private Oasis•Point Beach State Park•Lake Michigan
Private Oasis•Point Beach State Park•Lake MichiganTwo Rivers
The price is CA $191
CA $385 total
includes taxes & fees
Nov 17 - Nov 18
19. Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!New Holstein
10.0 out of 10, Exceptional, (182 reviews)
"We stay there every year and are never disappointed. Great location and experience. Thank you!"
Doug S.
The price is CA $321
CA $516 total
includes taxes & fees
Nov 29 - Nov 30
20. The Pines-Hike, Hunt, Hot tub Sleeps 9
The Pines-Hike, Hunt, Hot tub Sleeps 9Cascade
10.0 out of 10, Exceptional, (39 reviews)
"Great place for a lot of people to stay! Host was great! Hot tub was awesome. Very comfortable beds!! Will definitely be back."
Luke L.
The price is CA $485
CA $838 total
includes taxes & fees
Nov 18 - Nov 19
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.
Find vacation rentals that suit your style
Cabins
Cottages
Save an average of 15% on thousands of hotels when you're signed in
Top Sheboygan Hotel Reviews
Grandstay Residential Suites Hotel - Sheboygan
10/10 Excellent
Find out more about Sheboygan
Sheboygan Vacation Homes information
Number of reviews | 599 |
|---|---|
Accommodation | 255 Vacation Homes |
Lowest Price | CA $197 |
Highest Price | CA $1,448 |
Explore a world of travel with Expedia
- Unique Rustic Industrial Ryder Cup Rental…
- Aparthotels in Fond du Lac
- B&B in Byron
- Sheboygan Falls Hotels
- Harbor Winds Hotel
- Romantic Hotels in Manitowoc
- Cabin Rentals in Collins
- Baymont by Wyndham Plymouth
- Blue Harbor Resort and Conference Center
- Belgium Hotels
- Kohler Hotels
- Historic Hotels in Plymouth
- 4 Star Hotels in Manitowoc
- B&B in New Holstein
- Castles in Kohler
- Holiday Inn Manitowoc by IHG
- Aparthotels in Reedsville
- Port Washington Hotels
- Inn On Woodlake
- Harbor Town
- Cottages in Pike Lake
- Inviting
- Farmstay in Manitowoc County
- Apartment near many locations.
- Lodges in Fond du Lac
- Vacation Homes in Kohler
- Villas in Cedarburg
- Apartments in Dexter
- Apartments in Orchard Grove
- Guest Houses in Manitowoc
- Cabin Rentals in Elkhart Lake
- Pristine Beach Access
- Cottages in Cedarburg
- Manitowoc Hotels
- Kiel Hotels
- Motels in Pike Lake
- B&B in Dundas
- Hotels with Hot Tubs in Sheboygan
- Cabin Rentals in Ashford
- Vacation Homes in Pike Lake
- Hotels near Whistling Straits Golf Course
- The Esker Ridge Chalet
- Plymouth Hotels
- The Rochester Inn
- The Osthoff Resort
- Vacation Homes in Sherwood
- Condo Rentals in Byron
- Cottages in Two Rivers
- Sheboygan Hotels
- The Oasis Hotel & Bar
- Motels in Dundas
- Hotels near Stefanie H. Weill Center for the Performing Arts
- Hotels near Road America
- B&B in Cedar Grove
- Guest Houses in New Denmark
- B&B in Malone
- Saukville Hotels
- Motels in Ozaukee County
- Resorts in Wells
- Americinn by Wyndham Manitowoc
- The Inn on Maritime Bay
- Resorts in Cranberry Marsh
- Milwaukee Hotels
- Cedar Grove Hotels
- Flights to Plymouth
- Flights to Elkhart Lake
- Flights from Elkhart Lake
- Flights to Manitowoc
- Flights from Chicago (ORD) to Sheboygan (SBM)
- Flights from Toronto (YYZ) to Green Bay (GRB)
- Flights to Sheboygan
- Flights from Kohler
- Flights from Toronto (YYZ) to Milwaukee (MKE)
- Flights to Kohler
- Flights from Portland (PDX) to Manitowoc (MTW)
- Flights to Saukville
- Flights from Valders
- Flights from Indiana (IDI) to Sheboygan (SBM)
- Flights from Detroit (DTW) to Manitowoc (MTW)
- Flights from Columbus (CMH) to Sheboygan (SBM)
- Flights to Sheboygan Falls
- Flights from Toronto (YYZ) to Manitowoc (MTW)
- Flights to Belgium
- Flights from New York (NYC) to Manitowoc (MTW)
- Flights from Flint (FNT) to Manitowoc (MTW)
- Flights from Toronto (YTZ) to Manitowoc (MTW)
- Flights from Minneapolis (MSP) to Sheboygan (SBM)
- Flights from Sheboygan
- Flights from Mesa (AZA) to Manitowoc (MTW)