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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
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Compare 239 Vacation Homes in Sheboygan with updated reviews, rates, and availability.

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Dining area

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

10.0 out of 10, Exceptional, (15)
"Very comfortable space. "
The price is SAR 469
SAR 1,332 total
includes taxes & fees
18 Feb - 19 Feb
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Rear deck, yard and Lake Michigan view!

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

9.8 out of 10, Exceptional, (235)
"The house wasn't quite as clean as advertised. (I took photos.) Tracks on the floor, stuff in sink. Needed blankets in living room! Biggest issue is lack of communication. The locks were due to be changed after we checked out. We were not told until we were locked out of the house. After over an hour we were able to get back in, but the whole experience was unnecessarily stressful. If Mark is willing to give us a partial refund, we'd like to stay at the property again. My partner loved it, aside...
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Riverfront Townhome with GIANT Rec Room and Private Riverfront Deck
A sunny riverfront deck featuring loungers, a gas-fire table, and a coffee bar.

Riverfront Townhome with GIANT Rec Room and Private Riverfront Deck

9.8 out of 10, Exceptional, (20)
"Was cute, comfortable, fully stocked and within 10 minutes of pretty much everything! "
The price is SAR 469
SAR 898 total
includes taxes & fees
18 Feb - 19 Feb
Riverfront Townhome with GIANT Rec Room and Private Riverfront Deck
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Southeast side of property.

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

10.0 out of 10, Exceptional, (98)
"Highly recommend this place. No detail missed by this host."
The price is SAR 488
SAR 594 total
includes taxes & fees
19 Feb - 20 Feb
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Perfect Rating DT Home! Walk to Beach, Eats and More! 5 Min. to Road America!
Welcome to ElkHeart Escape!

Perfect Rating DT Home! Walk to Beach, Eats and More! 5 Min. to Road America!

10.0 out of 10, Exceptional, (71)
"We love staying here and will be back next year!"
Perfect Rating DT Home! Walk to Beach, Eats and More! 5 Min. to Road America!
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room
Ultra private lakefront home located on Lake Michigan shoreline.

Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

9.4 out of 10, Exceptional, (185)
"We stayed in the fall with family ranging from 7-65. The beach and view was so beautiful and relaxing. There was plenty of room to spread out or all be together. The games in the basement were the highlight for all ages. "
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room
NFL Draft!!! Spacious 4,500 Sq Ft 5-Bedroom Retreat House In Chilton!
Exterior

NFL Draft!!! Spacious 4,500 Sq Ft 5-Bedroom Retreat House In Chilton!

10.0 out of 10, Exceptional, (1)
"The house was outstanding! We had a group of five high school skiers and four adults and we all found the house to be very comfortable and inviting. There were so many well thought out details from the games in the garage to the extremely well equipped kitchen, cozy gas fireplace, plenty of living room throw blankets, abundant towels in the bathrooms, and comfortable beds. It was also extremely clean and the owner was so friendly! It was the perfect place for our team to cook, have a team...
NFL Draft!!! Spacious 4,500 Sq Ft 5-Bedroom Retreat House In Chilton!
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!
Private kitchen

NEW Three bedroom ranch style pet friendly home with a patio & theatre room!

10.0 out of 10, Exceptional, (27)
"Great house. Super clean ans spacious. We hosted family Christmas. Everything was perfect. Hope to stay again next year."
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!
4 Bedroom Beachfront Condo - Fantastic Lake View
Sandy beachfront right outside the front door

4 Bedroom Beachfront Condo - Fantastic Lake View

10.0 out of 10, Exceptional, (65)
"This was a great space for our friends weekend. Lots of comfy areas to relax and perfect location right on the beach! "
4 Bedroom Beachfront Condo - Fantastic Lake View
Lillibridge Lake Home on Tittle Lake/Long Lake All Season Fun
Exterior

Lillibridge Lake Home on Tittle Lake/Long Lake All Season Fun

9.6 out of 10, Exceptional, (130)
"This home had everything we needed for a relaxing family stay. We played games in front of the fire and exercised our dog in the (surprise!) fenced-in backyard. "
Lillibridge Lake Home on Tittle Lake/Long Lake All Season Fun
This house is a 5 bedroom(s), 4.5 bathrooms, located in Elkhart Lake, WI.
Exterior

This house is a 5 bedroom(s), 4.5 bathrooms, located in Elkhart Lake, WI.

2.0 star property
The price is SAR 1,950
SAR 4,017 total
includes taxes & fees
18 Feb - 19 Feb
This house is a 5 bedroom(s), 4.5 bathrooms, located in Elkhart Lake, WI.
Discover Lake Michigan steps away in your 4-bedroom retreat
Bring along your boat, toys, and fishing poles. Two kayaks included.

Discover Lake Michigan steps away in your 4-bedroom retreat

10.0 out of 10, Exceptional, (3)
"The Red Barn is a Historic Icon in the Two Rivers Community that has been beautifully restored and modernized making is a perfect vacation spot for our family. Many memories were created here; from the grandchildren learning to fish from the dock, catching enormous salmon from the lake to middle daughter getting engaged on this trip!!!"
Discover Lake Michigan steps away in your 4-bedroom retreat
Enjoy Lake Michigan sport fishing, beaches, and hiking trails.
Exterior

Enjoy Lake Michigan sport fishing, beaches, and hiking trails.

10.0 out of 10, Exceptional, (104)
"We’ve stayed here numerous times and it’s always been fine. "
Enjoy Lake Michigan sport fishing, beaches, and hiking trails.
Dog-Friendly Sheboygan Home - 1 Mi to Town!
Sheboygan Vacation Rental | 1BR | 1BA | 2 Steps to Enter | 860 Sq Ft

Dog-Friendly Sheboygan Home - 1 Mi to Town!

9.8 out of 10, Exceptional, (8)
"We just stayed there a few weeks ago and when we left we said we would definitely stay here again! Well equipped, exceptionally clean, and well located. Nice yard in the back for doggies, and the treats were nice! Management was very accommodating and easy to communicate with. Rick Doerr "
Dog-Friendly Sheboygan Home - 1 Mi to Town!
Riverfront Sheboygan Townhome w/ Grill!
Sheboygan Vacation Rental | 2BR | 1.5BA | 1,200 Sq Ft | Stairs Required

Riverfront Sheboygan Townhome w/ Grill!

10.0 out of 10, Exceptional, (13)
"My family and I were visiting family in Sheboygan over Christmas. The owner decorated the condo with a Christmas tree and other holiday decor. This condo was by far one of the most well put together condos we have stayed in. The toiletries in the condo were all high-end products. The condo was in a great location, property manager was responsive, and very clean. My family and I would definitely stay at the condo again. This condo is definitely a 5-star property. "
Riverfront Sheboygan Townhome w/ Grill!
Gleason's Chouse
Exterior

Gleason's Chouse

10.0 out of 10, Exceptional, (33)
"So interesting and comfy atmosphere. We loved all the attention to detail. Great amneties. Definitely going back!"
Gleason's Chouse
Modern Townhome w/ Deck - 1/2 Mi to Elkhart Lake!
Elkhart Lake Vacation Rental | 3BR | 2BA | 1,100 Sq Ft | Stairs Required

Modern Townhome w/ Deck - 1/2 Mi to Elkhart Lake!

10.0 out of 10, Exceptional, (35)
"Great location. Spacious rooms. Well appointed kitchen. Great management. Would definitely stay again. "
Modern Townhome w/ Deck - 1/2 Mi to Elkhart Lake!
Large House On Lake Michigan Beach NFL DRAFT only 40 minute drive Reserve Now !
Rear Windows Facing Lake Michigan

Large House On Lake Michigan Beach NFL DRAFT only 40 minute drive Reserve Now !

9.8 out of 10, Exceptional, (106)
"The house is amazing, My husband and I used the property for ourselves and our wedding party. It fit 24 people amazingly! The host was amazing and very responsive and SO accommodating!! Just an amazing place to be and relax between all the wedding things. If I could give more stars I absolutely would!! I loved it here!"
Large House On Lake Michigan Beach NFL DRAFT only 40 minute drive Reserve Now !
Sleeps 20 * 4,400 Sq Ft * Indoor Heated Pool

Sleeps 20 * 4,400 Sq Ft * Indoor Heated Pool

10.0 out of 10, Exceptional, (4)
"House was very spacious and plenty of room for our whole group. Adults and kids loved the pool space. Non swimmers should bring floats or life jackets as the one end is deep. Kitchen was nicely equipped with crock pot, blender and other utensils needed. Bring more toilet paper if you have a large group. Was super nice that the tree was still up the end of January. Highly recommended."
Sleeps 20 * 4,400 Sq Ft * Indoor Heated Pool
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Property grounds

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

10.0 out of 10, Exceptional, (22)
"We wish we lived here."
The price is SAR 334
SAR 847 total
includes taxes & fees
18 Feb - 19 Feb
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
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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Other property types in Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
Exterior

Grandstay Residential Suites Hotel - Sheboygan

2.5 star property
8.6 out of 10, Excellent, (889)
"The 2 separate, private bedrooms with the living room and kitchen worked very well for my family. "
The price is SAR 323
SAR 367 total
includes taxes & fees
18 Feb - 19 Feb
Grandstay Residential Suites Hotel - Sheboygan
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Rear deck, yard and Lake Michigan view!

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

9.8 out of 10, Exceptional, (235)
"The house wasn't quite as clean as advertised. (I took photos.) Tracks on the floor, stuff in sink. Needed blankets in living room! Biggest issue is lack of communication. The locks were due to be changed after we checked out. We were not told until we were locked out of the house. After over an hour we were able to get back in, but the whole experience was unnecessarily stressful. If Mark is willing to give us a partial refund, we'd like to stay at the property again. My partner loved it, aside...
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
REMODELED HOME ON LAKE MICHIGAN
Property grounds

REMODELED HOME ON LAKE MICHIGAN

10.0 out of 10, Exceptional, (146)
"Great place"
REMODELED HOME ON 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.