Maui Dream Wedding - Vacation Rentals in Downtown

REMODELED HOME ON LAKE MICHIGAN From US $176
         

9.8 (159 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan From US $391
         

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10.0 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Riverfront Sheboygan Townhome w/Grill! From US $244
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home From US $230
         

10.0 (111 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Beach front luxury spacious villa ! From US $325
         

10.0 (75 Reviews)
Villa
  • Air Conditioner
  • Parking
  • View
Malibu of the Midwest Condo steps from the Lake From US $249
         

Luxury Places to Stay in Downtown

Over 245+ Luxury Places to Stay in or Near Downtown
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygann From US $1,573
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Pelican Point - Private Retreat From US $1,250
         

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New
House
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  • View
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX From US $1,163
         

Top-Rated Vacation Rentals with a Pool in Downtown

Over 19+ Top-Rated Vacation Rentals with a Pool in or Near Downtown
Home2 Suites By Hilton Sheboygan From US $120
         

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9.6 (94 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Fairfield Inn & Suites by Marriott Sheboygan From US $106
         

9.4 (266 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Home2 Suites By Hilton Sheboygan From US $165
         

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9.3 (46 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Sheboygan-Kohler by IHG From US $89
         

8.8 (378 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Grandstay Residential Suites Hotel - Sheboygan From US $124
         

8.6 (1019 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
AmericInn by Wyndham Sheboygan From US $81
         

8.6 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Comfort Inn & Suites Sheboygan I-43 From US $86
         

8.6 (152 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Sheboygan-Kohler/I-43 by IHG From US $188
         

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8.5 (78 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Downtown

Over 61+ Pet-Friendly Vacation Rentals in or Near Downtown
*NEW* Sleeps 8 & Spacious! From US $186
         

10.0 (28 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Dog-Friendly Sheboygan Home - 1 Mi to Town! From US $261
         

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10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Accessibility
La Quinta Inn by Wyndham Sheboygan From US $87
         

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8.2 (1000 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Dog-Friendly Sheboygan Home - 1 Mi to Town! From US $125
         

10.0 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan From US $344
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Links! - Luxury Golf Retreat with Golf Simulator From US $414
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Eclectic Spacious 3 BR Home Near Lake MI w/Fire Pit From US $191
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Downtown on PetFriendly.io

Large Vacation Homes & Villas in Downtown

Over 56+ Large Vacation Homes & Villas in or Near Downtown
Spacious Sheboygan Home with Grill and Fire Pit! From US $563
         

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9.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Accessibility
Walk to Beach & Pier | Fully-Loaded Kitchen
New
From US $584
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
BEACHVIEW GETAWAY From US $241
         

9.8 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Downtown

Over 14+ Wheelchair Accessible Vacation Homes in or Near Downtown
Modern South Pier Condo on Sheboygan River! From US $229
         

9.4 (33 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Lake Orchard Farm Retreat From US $195
         

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8.9 (43 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • View
Watershed Hotel From US $136
         

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9.6 (482 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Fairfield Inn & Suites Sheboygan From US $245
         

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9.2 (46 Reviews)
Hotel
  • Parking
  • Wheelchair Accessible
  • Balcony/Terrace
Wingate by Wyndham Sheboygan From US $70
         

7.0 (153 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Waterfront Sheboygan Condo
New
From US $199
         

Downtown Varoom and Airbnb Places to Stay Under $200

Over 68+ Downtown Varoom and Airbnb Places to Stay Under $200
Riverfront Sheboygan Townhome w/Grill! From US $167
         

10.0 (29 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Spacious Home Near Lake MI w Fire Pit From US $151
         

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9.8 (9 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Harbor Winds Hotel From US $88
         

8.6 (939 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
BEACHSIDE GETAWAY IN SHEBOYGAN From US $154
         

10.0 (27 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Beachside Condo w/Stunning Lake Views From US $153
         

10.0 (25 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Beachside Condo Downtown with Lake Michigan Views From US $153
         

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI From US $197
         

Instantly Bookable Vacation Homes in Downtown

Over 110+ Instantly Bookable Vacation Homes in or Near Downtown
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown. From US $131
         

9.6 (11 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Family Home, 1 Block to Lake Michigan Beach! From US $375
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
LUXE Manor with Modern, Elegant Vibes From US $364
         

10.0 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
2 Mi to Dtwn: Studio Suite in Sheboygan From US $116
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

About Downtown Vacation Rentals

With more than 254 Downtown vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Mauidreamwedding and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Downtown.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Mauidreamwedding Downtown, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Downtown. Places to stay near Downtown are 753.2 ft² on average, with prices averaging $374 a night.

Mauidreamwedding makes it easy and safe to find and compare vacation rentals in Downtown with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Downtown

Type Count
Vacation Homes 117
Holiday Apartments 40
Hotels with Suites 23
Villas 13
Cottages 4
B&B 2
Cabin Rentals 1
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Downtown

Pro Tip: Mauidreamwedding makes it easy to compare the best listings on Mauidreamwedding homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Mauidreamwedding homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Downtown.

Weather in Downtown

View the weather forecast for Downtown before booking your Downtown Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Complexes around Downtown, WI