Vacation rentals in Waldo

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Top-rated vacation rentals in Waldo

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Oostburg

4.97 out of 5 average rating, 229 reviews

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.

Dec 10 – 17

$136 per night
Guest favorite

Home in Howards Grove

4.95 out of 5 average rating, 151 reviews

Spacious lower level priv entrance no cleaning fee

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. Unit NOT set up for babies or toddlers.

Dec 15 – 22

$95 per night
Guest favorite

Cabin in Elkhart Lake

4.99 out of 5 average rating, 188 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.

Sep 12 – 19

$213 per night

Popular amenities for Waldo vacation rentals

Other great vacation rentals in Waldo

Guest favorite

Townhouse in Port Washington

4.92 out of 5 average rating, 114 reviews

Steps Away From the Lakefront and Downtown

May 10 – 17

$81 per night
Guest favorite

Home in Sheboygan

4.97 out of 5 average rating, 146 reviews

Dog Friendly Blue Door Cottage / Fully Fenced Yard

Mar 16 – 23

$117 per night
Guest favorite

Home in Oostburg

4.96 out of 5 average rating, 164 reviews

Shamba on the Lake, Oostburg, WI

Apr 25 – May 2

$363 per night
Guest favorite

Home in Waldo

4.98 out of 5 average rating, 57 reviews

Perfect Winter Getaway!

Sep 27 – Oct 4

$119 per night
Guest favorite

Guest suite in Waldo

4.92 out of 5 average rating, 37 reviews

Above Garage Apartment w/ Private Beach

Apr 23 – 30

$86 per night
Guest favorite

Home in Plymouth

5.0 out of 5 average rating, 9 reviews

Cute and Cozy cape cod home

Nov 5 – 12

$79 per night
Guest favorite

Home in Plymouth

4.97 out of 5 average rating, 73 reviews

Sage Cottage

Aug 26 – Sep 2

$132 per night
Guest favorite

Home in Plymouth

4.94 out of 5 average rating, 80 reviews

Vintage Farmhouse on Blueberry Hill.

Nov 13 – 20

$146 per night
Guest favorite

Home in Sheboygan Falls

4.98 out of 5 average rating, 53 reviews

Adorable bungalow in historic Sheboygan Falls,WI

Sep 7 – 14

$133 per night
Guest favorite

Cabin in Cascade

4.88 out of 5 average rating, 17 reviews

Lakefront Cabin on Private Lake Community

May 10 – 17

$335 per night
Guest favorite

Cottage in Cascade

5.0 out of 5 average rating, 24 reviews

Stunning Lakefront Cottage with Private Beach

Apr 16 – 23

$468 per night
Guest favorite

Cabin in Cascade

5.0 out of 5 average rating, 31 reviews

modern woodland paradise w/ sauna

Oct 22 – 29

$370 per night

Destinations to explore

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  3. Wisconsin
  4. Sheboygan County
  5. Waldo