Holiday rentals in Waldo

4.99 out of 5 average rating, 273 reviews

Cabin in Elkhart Lake

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.

4.97 out of 5 average rating, 287 reviews

Cottage in Oostburg

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

4.97 out of 5 average rating, 118 reviews

Guest house in Plymouth

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

Flat 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.

5 out of 5 average rating, 123 reviews

Flat in Kohler

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

4.93 out of 5 average rating, 111 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!

4.95 out of 5 average rating, 176 reviews

Home in Howards Grove

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

Barn in Sheboygan Falls

4.71 out of 5 average rating, 106 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.

5 out of 5 average rating, 145 reviews

Cabin in Cascade

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!

5 out of 5 average rating, 214 reviews

Home in Sheboygan

Woodland Creek Retreat: explore & relax!

Lovely home nestled in 9 acres of peaceful woodland. 1.5 miles off I-43. Enjoy a walk in the woods or enjoy the dunes and wonderful views of Lake Michigan from Terry Andrae State Park only .2 miles away! Enjoy relaxing on the front porch or taking in the view of the woods from the spacious back deck. Be on the lookout for turkeys and deer. Wonderful wood burning fireplace and extensive game collection(500+) for staying in! We love the cozy and open cabin feel and hope you will too!

4.97 out of 5 average rating, 209 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.

4.98 out of 5 average rating, 150 reviews

Flat in Sheboygan

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.

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Other great holiday rentals in Waldo

5 out of 5 average rating, 34 reviews

Guest suite in Plymouth

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.

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 stars2 weeks 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.

5 out of 5 average rating, 13 reviews

Flat in Port Washington

Mariner's Point Carriage House

KellyRating, 5 stars2 days ago

Beautiful, quaint, cozy carriage house. Location was perfect, recommendations were great, deck with gas fire pit was perfect to unwind. Clean space. Very responsive! Thanks for enhancing our weekend getaway!

5 out of 5 average rating, 17 reviews

Updated Plymouth Home ~ 5 Mi to Road America!

JeffRating, 5 stars1 week ago

Had a wonderful stay. Was exactly like the photos. Super-easy check-in. Simple and very reasonable check-out instructions. Comfortable beds. Loved the Road America-themed decor! Would stay again.

4.97 out of 5 average rating, 92 reviews

Flat in Campbellsport

GGG Spacious Log Cabin apartment on the IAT

LaurenRating, 5 stars2 weeks ago

I’ve stayed here twice now and both times have been wonderful. The place is on the second floor, with the sweet owners below, and it is just the coziest space! My favorite thing to do is eat breakfast by the window with beautiful greenery and birds outside. Honorable mention goes to the bathtub! Many a sore muscle has been soothed after a long hike on the Ice Age Trail down the road. Carrie is awesome. She is super helpful and very quick to respond - it made me feel safe knowing they were just downstairs. Highly recommend this place!

Home in Sheboygan

4.78 out of 5 average rating, 23 reviews

Sheboygan Riverside Condo

AngelaRating, 5 stars1 week ago

Loved the place. Right on the river. Balcony view is great along with the fireplace! Renter was responsive and allowed us to check in early. Can’t wait to go back!

5 out of 5 average rating, 5 reviews

Stylish Ranch Near Road America

GregRating, 5 stars2 weeks ago

What a great place to stay! We attended races at Road America, and the location was perfect. The house is well-appointed, spotless, and has comfortable beds. Cooking was fun, and this place features some of the newest and best pans I've used in an Airbnb. The host was excellent with my questions and very responsive. I will be back next year!