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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 241 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 AED 459
AED 1,313 total
includes taxes & fees
24 Feb - 25 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 AED 459
AED 859 total
includes taxes & fees
24 Feb - 25 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, (99)
"This place is very clean and comfortable.The staff is very kindness. "
The price is AED 477
AED 581 total
includes taxes & fees
27 Feb - 28 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, (2)
"This house has lots of space for a large group--it is clean, well organized, and has nice furnishings. Great workable kitchen with plenty of dishes, glasses, cookware, etc. We loved the game room area and all the separate areas for sleeping. Nice to cozy up in living room with the fire going and plenty of throw blankets. Terrific place for our ski team to recover after racing at Ariens! Thank you for a fun stay!"
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, (28)
"Wonderful home! Great set up and very quick to respond with any questions. Definitely would come back!"
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, (66)
"We had the best stay! Thank you so much!"
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 AED 1,910
AED 3,934 total
includes taxes & fees
24 Feb - 25 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)
"Small cozy house with a great location. Was clean, organized, and suited well for bringing our dog."
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, (5)
"Katie & Josh's Vrbo was the perfect location for our family gathering of 20 people. The cleanliness of the space was truly impressive, and everyone appreciated how spacious and comfortable it was. Having access to fun amenities like the arcade and indoor pool added an extra layer of enjoyment to our stay. It was evident that this place was well-maintained and designed with guests in mind. We highly recommend this place to anyone looking to host a large group! "
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, (23)
"We picked the worst weekend of the year regarding snowfall, but we planned ahead. Jeff gave us the thumbs up for an early arrival, and my sister, my dog and I had a great girls weekend away from our spouses. We crafted, watched movies and made it a pajama party. The snow didn’t stop until the morning we were heading out. It was awesome, and Jeff’s crew was there to make sure we could get ourselves out. We will definitely be coming back in warmer weather. "
The price is AED 327
AED 830 total
includes taxes & fees
24 Feb - 25 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, (890)
"Beauty place excellent food options better than most"
The price is AED 316
AED 359 total
includes taxes & fees
24 Feb - 25 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.