Sheboygan Rentals

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21 Houses

(1) Excellent 

17

Lake Michigan by Whistling Straits

Wisconsin / Sheboygan

Sheboygan house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Child Friendly

Price per night from

$496

Responds fast!
avg. 1 hour 6 minutes

Price per night from

$496

(15) Excellent 

7

Lake Shore House on Lake Michigan! Dog Friendly!

Wisconsin / Sheboygan

Sheboygan house

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Child Friendly
“The Lakeshore House is just as nice as the pictures make it look!” My husband and I loved the Lakeshore House. It was cute, clean, and had beautiful views. There were many thoughtful surprises, like binoculars to view the birds and boats on the lake,
…see more

Price per night from

$95

Responds fast!
avg. 1 hour 41 minutes

Price per night from

$95

(2) Very Good 

18

REMODELED HOUSE ON LAKE MICHIGAN

Wisconsin / Sheboygan

Sheboygan house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.64 mi
  • Child Friendly

Price per night from

$126

Responds fast!
avg. 1 hour 42 minutes

Price per night from

$126

(1) Excellent 

19

Historic Mansion Right on Lake Michigan!

Wisconsin / Sheboygan

Sheboygan villa

9 25 3 nights min

  • 9 bedrooms
  • sleeps 25
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$1,487

Price per night from

$1,487

18

Bright and Beautiful Lake Escape

Wisconsin / Sheboygan

Sheboygan house

2 9 2 nights min

  • 2 bedrooms
  • sleeps 9
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$210

Price per night from

$210

15

Cozy house near the lake

Wisconsin / Sheboygan

Sheboygan house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$200

Price per night from

$200

(1) Very Good 

12

BEACHSIDE GETAWAY

Wisconsin / Sheboygan

Sheboygan condo

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$126

Price per night from

$126

19

REMODELED HOME OVERLOOKING LAKE MICHIGAN

Wisconsin / Sheboygan

Sheboygan house

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$335

Price per night from

$335

6

Centrally Located Sheboygan Charmer: Near Blue Harbor, Kohler & Lake MIchigan

Wisconsin / Sheboygan

Sheboygan house

4 7 2 nights min

  • 4 bedrooms
  • sleeps 7
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$151

Price per night from

$151

Great rentals within 20 miles that match your search

Distance approx 16.26 km from Sheboygan

28

3BR Elkhart Lake Townhome w/Multiple Porches

Wisconsin / Elkhart Lake

Elkhart Lake house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$426

Responds fast!
avg. 10 minutes

Price per night from

$426

Distance approx 10.06 km from Sheboygan

24

Charming Oostburg Home w/ Kayaks on Lake Michigan!

Wisconsin / Oostburg

Oostburg log cabin

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly

Price per night from

$181

Responds fast!
avg. 10 minutes

Price per night from

$181

Distance approx 15.97 km from Sheboygan

(12) Excellent 

32

Aspen House - Private, peaceful country home near Elkhart Lake

Wisconsin / Elkhart Lake

Elkhart Lake house

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Nearest beach 4 mi
  • Child Friendly
  • Air conditioning
“The best vacation rental ever!” I would like to start by thanking Nanette & Hans for their hospitality and personal caring to make my experience even more worthwhile. 95 private acres ... wow, you will feel like you own it! :) I felt completely comfo
…see more

Price per night from

$221

Responds fast!
avg. 22 minutes

Price per night from

$221

Distance approx 16.26 km from Sheboygan

26

Elkhart LakeTownhome w/Backyard- 1 Block to Beach!

Wisconsin / Elkhart Lake

Elkhart Lake house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$199

Responds fast!
avg. 53 minutes

Price per night from

$199

Distance approx 15.75 km from Sheboygan

24

NEW! Bright 4BR Plymouth Cottage on Crystal Lake

Wisconsin / Plymouth

Plymouth cottage

4 14 min stay varies

  • 4 bedrooms
  • sleeps 14
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$166

Responds fast!
avg. 10 minutes

Price per night from

$166

Distance approx 17.1 km from Sheboygan

10

Beautiful Victorian Near Racing, Golfing, & Hiking

Wisconsin / Glenbeulah

Glenbeulah house

4 7 2 nights min

  • 4 bedrooms
  • sleeps 7
  • 2 nights min

Price per night from

$451

Price per night from

$451

Distance approx 8.95 km from Sheboygan

19

Aunt Dot's Cottage on the Shores of Lake Michigan

Wisconsin / Oostburg

Oostburg house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly

Price per night from

$330

Price per night from

$330

Distance approx 15.2 km from Sheboygan

8

*Entertainment Villa. Close to Everything.*

Wisconsin / Elkhart Lake

Elkhart Lake villa

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$501

Price per night from

$501

Distance approx 19.36 km from Sheboygan

34

Cozy Valders Log Cabin -Gateway to Rural Wisconsin

Wisconsin / Valders

Valders log cabin

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly

Price per night from

$200

Responds fast!
avg. 10 minutes

Price per night from

$200

Distance approx 15.18 km from Sheboygan

(2) Excellent 

12

*Luxury Villa. Brilliant Location. Guest Approved.*

Wisconsin / Elkhart Lake

Elkhart Lake villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$801

Price per night from

$801

Distance approx 11.41 km from Sheboygan Show on Map

(1) Very Good 

17

RESToration House

Wisconsin / Cleveland

Cleveland house

1 6 3 nights min

  • 1 bedroom
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$151

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$151

Distance approx 10.51 km from Sheboygan

21

Great Place on a Great Lake 15 minutes from "Destination Kohler"

Wisconsin / Oostburg

Oostburg house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 0 mi
  • Child Friendly
  • Air conditioning

Price per night from

$251

Price per night from

$251