Too Doo - Vacation Rentals in Downtown

Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan From US $374
         

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10.0 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Holiday Inn Express Sheboygan-Kohler by IHG From US $192
         

8.8 (393 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Beach front luxury spacious villa ! From US $484
         

10.0 (90 Reviews)
Villa
  • Air Conditioner
  • Parking
  • View
Malibu of the Midwest Condo steps from the Lake From US $318
         

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced From US $341
         

BEACHSIDE GETAWAY IN SHEBOYGAN From US $315
         

10.0 (29 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Riverfront Sheboygan Townhome w/Grill! From US $193
         

10.0 (29 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Family Home, 1 Block to Lake Michigan Beach! From US $383
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Downtown

Over 246+ Luxury Places to Stay in or Near Downtown
Baronwood Oasis | Pool + Arcade Mega Estate From US $2,398
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Pelican Point - Private Retreat From US $1,250
         

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New
House
  • Air Conditioner
  • Parking
  • View
Walk to Beach & Pier | Fully-Loaded Kitchen From US $1,212
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Villa on Lake Michigan! From US $1,074
         

10.0 (13 Reviews)
Villa
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in Downtown

Over 18+ Top-Rated Vacation Rentals with a Pool in or Near Downtown
Home2 Suites By Hilton Sheboygan From US $165
         

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9.2 (60 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Downtown, Uniquely Designed, Near the Beach From US $279
         

8.8 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Sheboygan-Kohler/I-43 by IHG From US $335
         

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8.6 (84 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Quality Inn Sheboygan North I-43 From US $107
         

8.2 (794 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
GrandStay Hotel & Suites Downtown Sheboygan From US $216
         

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8.2 (234 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
AmericInn by Wyndham Sheboygan From US $87
         

8.1 (139 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Comfort Inn & Suites Sheboygan I-43 From US $102
         

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8.0 (147 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Quality Inn Sheboygan North I-43 From US $89
         

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7.5 (250 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Downtown

Over 55+ Pet-Friendly Vacation Rentals in or Near Downtown
Dog-Friendly Sheboygan Home - 1 Mi to Town! From US $181
         

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9.7 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • Balcony/Terrace
La Quinta Inn by Wyndham Sheboygan From US $124
         

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8.2 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan From US $367
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Links! - Luxury Golf Retreat with Golf Simulator From US $616
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Eclectic Spacious 3 BR Home Near Lake MI w/Fire Pit From US $274
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI From US $170
         

See More Pet-Friendly Vacation Rentals in Downtown on PetFriendly.io

Large Vacation Homes & Villas in Downtown

Over 58+ Large Vacation Homes & Villas in or Near Downtown
Lake Orchard Farm Retreat From US $203
         

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9.2 (37 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Wandering Waves - Beachfront Lake Michigan Stay! From US $452
         

BEACHVIEW GETAWAY From US $379
         

9.8 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Lake Orchard Farm Cottage From US $791
         

9.6 (9 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Downtown

Over 17+ Wheelchair Accessible Vacation Homes in or Near Downtown
Fairfield Inn & Suites Sheboygan From US $245
         

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8.8 (53 Reviews)
Hotel
  • Parking
  • Designated Smoking Area
  • Wheelchair Accessible
Waterfront Sheboygan Condo From US $653
         

Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home From US $376
         

10.0 (116 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Downtown waterfront condo. Full hook-up boat slip! Close to beach! Private deck! From US $150
         

10.0 (60 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area
Corner River Walk Condo with Spectacular Views From US $249
         

10.0 (45 Reviews)
Condo
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace
Modern South Pier Condo on Sheboygan River! From US $476
         

9.6 (35 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV

Downtown Vacation Rentals and Airbnb Places to Stay Under $200

Over 43+ Downtown Vacation Rentals and Airbnb Places to Stay Under $200
Super 8 by Wyndham Sheboygan WI From US $84
         

6.6 (851 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan From US $160
         

Pet-Friendly Sheboygan Home: 4 Mi to Lake Michigan From US $178
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Sunset Vista – 2BR Central Elkhart Lake Retreat From US $162
         

Instantly Bookable Vacation Homes in Downtown

Over 111+ 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
Beautiful 3BR Home Near Lake MI From US $442
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV
Sheboygan Riverside Condo From US $302
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV
Storybook 2-bedroom apartment 1mi from Lake Michigan From US $204
         

About Downtown Vacation Rentals

With more than 255 Downtown vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Toodoo 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 Toodoo 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 757.34 ft² on average, with prices averaging US $431 a night.

Toodoo 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 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: Toodoo makes it easy to compare the best listings on Toodoo homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Toodoo 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


Downtown Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Downtown?
How many vacation rentals have private pools in Downtown?

There are 1 vacation rentals with private pools near Downtown. Top-rated homes that have access to a swimming pool include:

How many vacation rentals are available in Downtown?

Currently, the total number of properties listed in 2026 is over 255 in the Downtown area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Downtown.