
Places to stay near Deland Park
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Top-rated holiday rentals near Deland Park
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Modern Upstairs Apt - Steps from Lake Michigan
Have you ever wondered what Lake Life is like? Here is your chance! This is 1 of 2 AirBnB units in this cute duplex Come stay in this beautiful upper apartment located just one block from Lake Michigan. Take a quick walk to the lake in the morning to jump on your fishing boat or take the family to the beach in the afternoon! Located close to shopping and many local bars and restaurants within walking distance. You'll find relaxation and a great time here at the heart of Sheboygan's Shoreline!

Spacious/stylish, 2br loft
Beautiful, spacious loft in active downtown. Washer/dryer, full kitchen, 1.5 baths, 2 Qu, 2 Tw, space for family/friends. Stocked w/home essentials. 3 Smart TVs, free WIFI. Pay-as-you-go parking in rear but free nights/weekends. Bakery & fitness studio on 1st floor. Wonderful walkable neighborhood near shops, restaurants, art & children’s museum, river walk & lake front near-by. Short drive to Kohler, Whistling Straits golf course, Shops at Woodlake & Kohler Design Center. Marcus cinema near by.

Boutique Wellness Retreat - Hot Tub and Fireplace
Celebrate your special occasion in Sheboygan at this beautiful boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom w/King size bed. Secondary bedroom has 2 twin beds. The beautiful fireplace in the living room is perfect for a relaxing couples evening. Enjoy a glass of wine or local brew on the patio while you grill out. EV Charger and E-Bikes to explore the area. Let us impress you and help make it a memory.

LUX Downtown Escape | Outdoor Movie Screen
Welcome to our beautiful 2-bedroom historic home in Downtown Sheboygan! This charming and well-appointed residence offers a comfortable and stylish stay for your visit to the area. From the Chef’s kitchen, comfortable living room, and peaceful backyard, to its prime location within walking distance of Sheboygan's vibrant nightlife, theater, and restaurants, you'll have everything you need right at your doorstep. The home is also just a few blocks from Lake Michigan's beautiful beaches.

Beach and golf house
This home is in the perfect location to explore everything Sheboygan County has to offer. It is located in the historic Ellis district on the shores of beautiful Lake Michigan. The home is a 2 or 3 minute walk to Deland Beach and the Sheboygan Marina and lighthouse. A short drive to world class golfing at Whistling Straights, Black Wolf Run and The Bull. Road America is also a short 20 minute drive. Located half way between Green Bay and Milwaukee for those Packer and Brewer fans.

hot tub and sauna on 5 private acres
Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

Lovely modern two bedroom home with fire pit
Newly renovated two bedroom home just a mile from the beach and five star restaurants. Enjoy a game of golf at world class Whistling Straight. Car enthusiasts will love Elkhart Lake Road America. Salmon fishing the Great Lake Michigan or just have a relaxing time around the fire pit. There is a laundry with washer/dryer, steamer and folding table. Dogs under 30 pounds. No cats sorry. No smoking in the house. Ample street parking at the front door. Fire pit in back yard.

Logan's Guest Nest
Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

Stylish Getaway | Cozy Vibes | Perfect Girls Trip
Escape to a cozy, stylish retreat designed for relaxing weekends, girls trips, or family getaways. Start your morning with a sunrise and coffee on the patio looking out onto Lake Michigan, then spend the day exploring, and unwind at night around the firepit with a glass of wine. This home has everything you need for gathering and cooking together or cozying up to the fireplace and playing board games. A short walk to town, close to golf, breweries, winery, and a state park.

Cozy Sheboygan Upper
We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

Church Street Romance & Retreats-Village of Kohler
“A well-appointed, cozy and stylish retreat close to everything in Kohler.” -Kim Take the stairs to my secluded 2nd floor tree view retreat! A private side entrance and open floor plan flanked by two bedrooms makes this unit perfect for couples or a girl's getaway spa weekend. Romantic turn-of-the-century touches meet modern convenience & comfort. Baker furniture, previously a Kohler Company, can be found throughout the apartment enhancing your Village of Kohler stay.

The Suncatcher -Steps from Lake - Fenced Yard
Welcome to the Suncatcher. Our cozy and bright Midwest retreat just a block away from Lake Michigan . Step into our lovingly remodeled 1930's home where modern comfort meets timeless charm. As you enter you will be greeted by the inviting warmth of exposed brick walls and abundance of natural light that fill every corner. With three bedrooms and two bathrooms, our spacious retreat is perfect for families, friends, or golf enthusiasts seeking a relaxing getaway.
Popular amenities for holiday rentals near Deland Park
Condo rentals with Wi-Fi

Welcome to our Cozy Lake Condo!

VicVill | WaterViews | Vintage Charm Meets Comfort

Riverfront Condo Steps to Downtown & Lake Michigan

Amazing views beach condo for 12: 4 bdrm, 3 bath

Beachside Condo Downtown with Lake Michigan Views

Car Condo Rental in Elkhart Lake

Beachside Lake View - 2br - First Floor - Garage

Private Beach, Pools & Full-Kitchen
Family-friendly house rentals

2 Min Walk to Food, 15 to Pier! 4 Bedrooms 2K/2Q

House Near the Lake

Beachside Beautifully Renovated Historic Home

King Bed Near Lake w/ Fire Pit & Pack N Play

Relaxing Sheboygan/Kohler Getaway

Designer Victorian Near Lake Michigan & Downtown

Spacious lower level priv entrance no cleaning fee

Lakefront Charmer, cheerful decor gorgeous garden
Apartment rentals with air conditioning

The Blue Cobb House

NEW Riverfront Loft - Fantastic location

Heart of Downtown Sheboygan

Fully Loaded and Clean! King

Local Landmark CF / Artisan Coffeehouse

Storybook Home - 1 mi to Lake & Downtown Sheboygan

The Beach | Sheboygan 2Br/1 Ba

Welcome to Harbor Nights!
Other great holiday rentals near Deland Park

Boutique Gallery House - Stay inside a Work of Art

Luxury Villa on Lake Michigan!

Unmatched Location, Views, & Style. Welcome Home!

Lake Breeze Cottage Walk to beach, marina, shops.

Wandering Waves | Beachfront Lake Michigan Stay!

Luxury 4B-2Ba Lake & Beach House

Family Cottage, Walk to the lake (pet friendly)

Sheboygan Riverside Condo
Destinations to explore
- Kohler-Andrae State Park
- Whistling Straits Golf Course
- Bradford Beach
- Eaa Aviation Museum
- Blackwolf Run Golf Course
- Holy Hill National Shrine of Mary
- Atwater Park
- Paine Art Center And Gardens
- Fox Cities Performing Arts Center
- Lake Park
- Little Switzerland Ski Area
- Road America
- The Bull at Pinehurst Farms Golf Course
- Lion's Den Gorge Nature Preserve
- Neshotah Park
- Wisconsin Maritime Museum





