North Berkeley Cottage - Vacation Rentals in Downtown

Lake Orchard Farm Cottage From US $791
         

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

Luxury Places to Stay in Downtown

Over 250+ Luxury Places to Stay in or Near Downtown
Baronwood Oasis | Pool + Arcade Mega Estate From US $3,008
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Walk to Beach & Pier | Fully-Loaded Kitchen From US $1,641
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pelican Point - Private Retreat From US $1,250
         

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New
House
  • Air Conditioner
  • Parking
  • View

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 $130
         

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9.6 (110 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Fairfield Inn & Suites by Marriott Sheboygan From US $192
         

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9.4 (283 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Home2 Suites By Hilton Sheboygan From US $165
         

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9.2 (60 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Sheboygan-Kohler by IHG From US $196
         

8.8 (392 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Downtown, Uniquely Designed, Near the Beach From US $318
         

8.8 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Grandstay Residential Suites Hotel - Sheboygan From US $211
         

8.6 (1040 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Comfort Inn & Suites Sheboygan I-43 From US $108
         

8.6 (194 Reviews)
Hotel
  • 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

Pet-Friendly Vacation Rentals in Downtown

Over 59+ Pet-Friendly Vacation Rentals in or Near 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
La Quinta Inn by Wyndham Sheboygan From US $117
         

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8.2 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced From US $355
         

*NEW* Sleeps 8 & Spacious! From US $385
         

10.0 (28 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Dog-Friendly Sheboygan Home - 1 Mi to Town! From US $161
         

10.0 (23 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan From US $374
         

10.0 (14 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 59+ 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
Beach front luxury spacious villa ! From US $590
         

10.0 (90 Reviews)
Villa
  • Air Conditioner
  • Parking
  • View
Wandering Waves - Beachfront Lake Michigan Stay! From US $441
         

Pelican Point - Private Retreat - just 4 miles to downtown Sheboygann From US $1,040
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Wheelchair Accessible Vacation Homes in Downtown

Over 17+ Wheelchair Accessible Vacation Homes in or Near Downtown
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home From US $376
         

10.0 (115 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Fairfield Inn & Suites Sheboygan From US $245
         

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8.8 (53 Reviews)
Hotel
  • Parking
  • Designated Smoking Area
  • Wheelchair Accessible
Malibu of the Midwest Condo steps from the Lake From US $318
         

Modern South Pier Condo on Sheboygan River! From US $465
         

9.6 (35 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Waterfront Sheboygan Condo From US $435
         

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

Downtown Vacation Rentals and Airbnb Places to Stay Under $200

Over 49+ Downtown Vacation Rentals and Airbnb Places to Stay Under $200
Riverfront Sheboygan Townhome w/Grill! From US $193
         

10.0 (29 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Harbor Winds Hotel From US $159
         

8.6 (965 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI From US $170
         

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan From US $160
         

2 Mi to Dtwn: Studio Suite in Sheboygan From US $154
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Lake Breeze on 11th From US $170
         

9.6 (13 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
COMFY, COZY, and CONVENIENT! From US $123
         

10.0 (62 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Downtown

Over 115+ Instantly Bookable Vacation Homes in or Near Downtown
REMODELED HOME ON LAKE MICHIGAN From US $539
         

9.8 (165 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
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
Beachside Condo w/Stunning Lake Views From US $473
         

10.0 (32 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Beachside Condo Downtown with Lake Michigan Views From US $402
         

BEACHSIDE GETAWAY IN SHEBOYGAN From US $331
         

10.0 (29 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Family Home, 1 Block to Lake Michigan Beach! From US $396
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Cottage - Newly Renovated Beachfront Condo on Lake Michigan From US $415
         

10.0 (21 Reviews)
Condo
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

About Downtown Vacation Rentals

With more than 4 Downtown vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Northberkeleycottage 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 Northberkeleycottage 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 750 ft² on average, with prices averaging US $404 a night.

Northberkeleycottage 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
Cottages 4

Use these Quick Filters to Find a Vacation Rental in Downtown

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

How many vacation rentals are available in Downtown?

Currently, the total number of properties listed in 2026 is over 4 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.