Vacation rentals in Waldo

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Top-rated vacation rentals in Waldo

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Top guest favorite

Cabin in Elkhart Lake

4.99 out of 5 average rating, 269 reviews

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

Guest favorite

A red cottage is set among lush green trees, with a winding driveway leading to its entrance. The pathway is bordered by neatly trimmed shrubs, creating a natural environment. The structure features a gabled roof and is partially obscured by the surrounding foliage.

Guesthouse in Plymouth

4.97 out of 5 average rating, 118 reviews

Woodside Cottage Guest House-Close to Road America

Woodside Cottage in the Kettle Moraine forest of East Central Wisconsin offers a quiet private getaway for Road American race fans, golfers or those wanting just to have a break from the city and explore the area. This 2 bedroom guesthouse can host 8, with laundry, full kitchen, living room and outdoor fire pit. Due to family guest allergies, we are pet free. Located 4 miles from gate 4 at Road America and 20 miles from Whistling Straits golf course. WIFI available, but unreliable. 3 cars MAX

Superhost

A simple entrance is highlighted by a white door adorned with a small window, framed by green siding. A festive decoration, resembling a snowman, composed of evergreen branches and a golden hat, is positioned beside the door, adding a cheerful touch.

Apartment in Plymouth

4.64 out of 5 average rating, 311 reviews

Pineyard Plymouth Apartment

Enjoy this older upper floor apt. with two single bedrooms with a twin bed in one and a full bed in the other, full bath, kitchen, living room, and off street parking. VCR/DVD player and internet is available. Kitchen is equipped with dishes, pots, pans, stove, and refrigerator. We are five minutes from Road America, fifteen minutes from Sheboygan, and thirty minutes from Fond du Lac. Only three blocks from downtown Plymouth enjoy many shops and eating establishments. Pets are NOT allowed.

Top guest favorite

Apartment in Kohler

5 out of 5 average rating, 123 reviews

The Hemingway on Church - It Tolls For Thee

"Kristine's property has all the charm of a modern day Mayberry" -Michael This 1906 historic home is nestled in the heart of the equally historic "Village of Kohler." Completely remodeled in 2019 adding Kohler spa amenities and modern touches to its original charm. Mixing modern & antique furniture finds like the Hemingway Sideboard (which inspired the literary theme) make this historic hideaway a true Kohler destination. "You cannot get a better location in Kohler than this house!" -Dennis

Guest favorite

Home in Plymouth

4.93 out of 5 average rating, 110 reviews

Vintage Farmhouse on Blueberry Hill.

Relax with the whole family at this peaceful place to stay. Located conveniently half way between Green Bay and Milwaukee. Find your self minutes away from Road America, Whistling Straits, snowmobile trails, kettle moraine state forest, and so much more. Our property has walking trails to the river, throughout the woods and around the creek area, This winter you would have the opportunity to snowshoe our 103 acre property, or break your own cross country ski trail! Or just a quiet getaway!

Guest favorite

A light blue front door is framed by neatly arranged red brick columns. Two lantern-style light fixtures are mounted on either side, providing a welcoming entrance. The door features a grid of glass panes, allowing natural light to illuminate the area.

Home in Sheboygan

4.94 out of 5 average rating, 234 reviews

Dog Friendly Blue Door Cottage / Fully Fenced Yard

Nobody should have to leave their fur baby behind while on vacation. This is exactly why we created this comfortable home with your family & puppy in mind. You'll be at ease knowing that your pooch will be having just as much fun as you are. Modern hints are complemented by the cozy, welcoming decor found throughout. The coffee bar is a fav for any morning person, and the "take-a-wine leave-a-wine" wine bar offers evening excitement! The huge yard features a fire pit, gas grill, & cornhole.

Top guest favorite

An exterior view of the property features a wooden deck above with a railing, complemented by a staircase leading to the entrance. A paved area at the ground level includes plants and a grill, alongside a garage door and multiple windows of the main structure.

Home in Howards Grove

4.95 out of 5 average rating, 176 reviews

Spacious lower level priv entrance no cleaning fee

Not set up for babies or toddlers. Entire basement is for rent with a separate entrance. Kitchen area includes refrigerator, microwave, coffee pot, toaster, sink, dining table and chairs. NO STOVE OR OVEN IS AVAILABLE. Free Wifi and Cable TV. Air conditioning. Plenty of parking, keyless entry. 14 min to Road America, 13 min to Kohler, 9 min to Whistling Straits, 5 min to Lakeland University, 1 hr to Milwaukee, 1 hr to Green Bay. Lots of nice amenities, clean, spacious. No cleaning fee.

Superhost

An aerial view captures the layout of the property, showcasing a cluster of buildings surrounded by lush greenery and a small pond. Farm fields extend in all directions, while trees add a touch of vibrant color to the landscape.

Barn in Sheboygan Falls

4.71 out of 5 average rating, 105 reviews

Quiet Country Charm

Cozy barn loft with rustic charm. This newly renovated private loft sleeps 4 with the possibility of 1 or 2 more if you don’t mind sleeping on an air mattress. This room includes a bathroom with shower and small efficiency kitchen with microwave, coffee maker, and small refrigerator. The futon pulls out to a double bed. This relaxing local comes complete with barnyard animals for an authentic Wisconsin experience! You won’t forget the peaceful surroundings of this rustic destination.

Top guest favorite

The cabin's exterior features a modern design with a dark green facade and a sloped metal roof. Large windows reflect the surrounding greenery, while a gravel pathway leads to the entrance, framed by vibrant foliage and a landscaped yard.

Cabin in Cascade

5 out of 5 average rating, 143 reviews

hot tub and sauna on 5 private acres

Need 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 inspired getaway awaits!

Top guest favorite

A vibrant display of northern lights fills the night sky, showcasing swirling shades of green and hints of purple. Soft, cloud-like formations can be seen amidst scattered twinkling stars, creating a mesmerizing atmosphere.

Home in Plymouth

4.97 out of 5 average rating, 208 reviews

Wyatt's Country Home - King Bed

Soak up the modern vintage charm of our fully remodeled and updated home! Thank you for choosing our sparkling clean space. Our home is nestled on two quiet acres just north of Plymouth in the peaceful country. Enjoy coffee as the sun rises from one of the two decks, or perhaps a cocktail by the fire as the sun sets. We ourselves lived in this home for our first 5 years and turned it into a beautiful and peaceful space for ourselves that we would now like to share with everyone.

Top guest favorite

A round wooden dining table is surrounded by four white chairs, set against a light grey carpet featuring a geometric pattern. A bowl of yellow fruit sits in the center of the table. Natural light streams in from the adjoining area, enhancing the neutral tones of the space.

Apartment in Sheboygan

4.98 out of 5 average rating, 148 reviews

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.

Top guest favorite

A sandy beach is set against a clear blue sky, with gentle waves lapping at the shore. Lush green grass borders the beach area, while several volleyball nets are positioned on the sand, indicating recreational opportunities nearby.

Apartment in Sheboygan

4.93 out of 5 average rating, 500 reviews

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.

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Other great vacation rentals in Waldo

Guest favorite

A circle of six red Adirondack chairs is arranged around a small fire pit, partially surrounded by rocky edging. Lush greenery and trees provide a natural backdrop, creating a secluded outdoor gathering space.

Guest suite in Plymouth

5 out of 5 average rating, 34 reviews

Riverside Suite

EddieRating, 5 stars8 months ago

Very nice space and a great neighborhood to stay. Nicest suite I have ever stayed. Good area to just take an eveing walk. Easy access to town with a lot going on and very classy. Will happily return to the suite and enjoy more of what the area has to offer.

Top guest favorite

A red barn with white accents is set against a vibrant sunset sky. The grassy area is framed by wooden fencing, providing a serene rural backdrop. Soft clouds reflect warm colors in the evening light, enhancing the peaceful countryside landscape.

Home in Plymouth

5 out of 5 average rating, 10 reviews

Large House near Road America. Breakfast Included!

AyanoRating, 5 stars2 months ago

Frances’ place was amazing. She greeted us at the beautiful house and gave us a tour, which was very much appreciated. The house is large enough for many adults, and child friendly. There are several of beds, bedrooms, and we never felt crowded in the house (9 adults and 1 child). My toddler very much appreciated all the toys in the house, board games, and loved running through the house. The daily breakfast was lovely, and delicious. There were also several snacks and treats in the kitchen which any kid or adult would love. I can’t say enough good things about Frances’ Airbnb. We can’t wait to be back!

Guest favorite

The modern structure features a striking combination of large windows and a red roof. Surrounded by lush greenery, the exterior reflects a contemporary design with clean lines. A vehicle is parked nearby, indicating accessibility and convenience.

Place to stay in Plymouth

4.98 out of 5 average rating, 86 reviews

The Loft at Hickory Haven-A Modern Rural Studio

CarrieRating, 5 stars1 week ago

Hickory Haven lived up to its name! The surroundings are beautiful and the loft was pristine! This is the cleanest airbnb I have stayed in - everything was perfect. Our host, Mary, left several special touches like fresh fruit and local cream to make us feel right at home. This place is truly an oasis.

Guest favorite

A spacious interior showcases wooden walls and beams, creating a warm ambiance. A large dining table is positioned at the center, surrounded by wooden chairs. The living area includes comfortable seating, a wood-burning fireplace, and large windows that offer ample natural light.

Cabin in Cascade

5 out of 5 average rating, 12 reviews

Lakeside Cabin Retreat Relax at Private Lake House

WendyRating, 5 stars1 week ago

The accommodations were perfect for our short stay and Meghan was very responsive and helpful with our needs. We would love to visit again when we have more time to use all of the outdoor amenities.

Guest favorite

A bright corner features a comfortable chair next to a small table, set in front of large windows with blinds. A full-length mirror reflects the room, which showcases a stylish rug on the wood-like flooring and a glimpse of the bed in the background.

Apartment in Sheboygan Falls

4.86 out of 5 average rating, 7 reviews

Elegant Condo in Sheb Falls

AlbertoRating, 5 stars10 months ago

Great place to stay for Road America.... will definitely stay here again!

Top guest favorite

A fire pit is featured at the center of a wooden table, surrounded by dark volcanic rocks. Flames dance above the fire ring, creating a warm glow. Two chairs are positioned nearby, offering a cozy spot for gathering outdoors.

Apartment in Port Washington

5 out of 5 average rating, 10 reviews

Mariner's Point Carriage House

LindaRating, 5 stars5 days ago

Was traveling solo and found the Carriage house to be easy to find and get into thanks to Lori's instructions. The finishes (countertops, window blinds, shower) are so lovely. It's nice to be able to enjoy a place that doesn't look like every other boring AirBnB. The bed was comfortable and the neighborhood was so quiet and walkable. The book of instructions and recommendations was a great resource. I had a few hours to relax in between activities and had a fun, cozy time watching a movie, listening to the gentle rain outside and enjoying some homemade treats provided by the hosts. When the sun came out, the neighbors could be seen walking their dogs, gathering together at local spots, and enjoying the lake. I can't wait to come back in the Fall.

Top guest favorite