Waldo Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Waldo vacation rentals

Lobby

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,033 reviews)
"Staff was friendly and room was nice and clean."
United States
Amelia
The price is ￥18,933
￥21,488 total
includes taxes & fees
May 24 - May 25
Grandstay Residential Suites Hotel - Sheboygan
Cabin, Lake View | Beach

Tiki Beach Campground

Tiki Beach Campground
3.0 star property
Campbellsport
10.0 out of 10, Exceptional, (1 review)
"Beautiful"
United States
Angela
The price is ￥30,161
￥31,820 total
includes taxes & fees
May 19 - May 20
Tiki Beach Campground
Apartment (2 Bedrooms) | Front of property

Modern South Pier Condo on Sheboygan River!

Modern South Pier Condo on Sheboygan River!
4.0 star property
Sheboygan
The price is ￥25,557
￥62,029 total
includes taxes & fees
Jun 1 - Jun 2
Modern South Pier Condo on Sheboygan River!
Children's area

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Oostburg
10.0 out of 10, Exceptional, (129 reviews)
"Welcoming and accommodating host, very clean and cozy cottage, amazing fireplace "
United States
Cade R.
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Terrace/patio

Stunning private home hidden in the woods. Can sleep 11 guests

Stunning private home hidden in the woods. Can sleep 11 guests
Plymouth
10.0 out of 10, Exceptional, (15 reviews)
"Very clean and private property! "
United States
sherine m.
The price is ￥126,992
￥153,068 total
includes taxes & fees
May 18 - May 19
Stunning private home hidden in the woods. Can sleep 11 guests
Dining

Beautiful 3BR Home Near Lake MI

Beautiful 3BR Home Near Lake MI
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Very family friendly . Great bike trails"
United States
Thomas D.
The price is ￥30,173
￥68,483 total
includes taxes & fees
May 18 - May 19
Beautiful 3BR Home Near Lake MI
Outdoor dining

Inviting, Rustic Beach front cottage on Beautiful Lake Michigan

Inviting, Rustic Beach front cottage on Beautiful Lake Michigan
OOSTBURG
9.8 out of 10, Exceptional, (75 reviews)
"Cottage was very comfortable, we had a great stay."
United States
Kathy M.
The price is ￥51,591
￥110,030 total
includes taxes & fees
Jun 2 - Jun 3
Inviting, Rustic Beach front cottage on Beautiful Lake Michigan
Interior

Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (42 reviews)
"Incredibly decorated home. Loved staying here. "
United States
Mike L.
The price is ￥21,430
￥30,648 total
includes taxes & fees
May 18 - May 19
Gleason's Chouse
Interior

Apartment Centrally Located

Apartment Centrally Located
Plymouth
The price is ￥19,049
￥30,839 total
includes taxes & fees
May 24 - May 25
Apartment Centrally Located
Smart TV

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Sheboygan
9.8 out of 10, Exceptional, (26 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is ￥50,003
￥95,852 total
includes taxes & fees
May 18 - May 19
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Exterior detail

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
New Holstein
10.0 out of 10, Exceptional, (174 reviews)
"Great place would go back"
United States
William
The price is ￥32,145
￥53,173 total
includes taxes & fees
May 24 - May 25
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Living area

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Ellis Historical District
9.6 out of 10, Exceptional, (12 reviews)
"A warm and cozy place to stay. Beautifully decorated and friendly hosts. Would stay again anytime we’re in Sheboygan."
United States
Rebecca S.
The price is ￥18,255
￥24,324 total
includes taxes & fees
May 19 - May 20
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
House (2 Bedrooms) | Interior

Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
Sheboygan
The price is ￥24,287
￥64,996 total
includes taxes & fees
May 31 - Jun 1
Large Backyard, Walk to Hospital: Sheboygan Abode!
Interior

Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Kiel
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful place! "
United States
Colleen & Mark G.
The price is ￥57,146
￥97,301 total
includes taxes & fees
May 19 - May 20
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Exterior

Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.6 out of 10, Exceptional, (5 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
The price is ￥14,287
￥47,386 total
includes taxes & fees
May 18 - May 19
Logan Ave Holiday House - Upper
Interior

Apartment near many locations.

Apartment near many locations.
Plymouth
10.0 out of 10, Exceptional, (1 review)
"Nice stay good prorpety and quiet"
United States
reginald o.
The price is ￥41,114
￥56,420 total
includes taxes & fees
May 24 - May 25
Apartment near many locations.
Fridge, microwave, oven, stovetop

The Links! - Luxury Golf Retreat with Golf Simulator

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (8 reviews)
"Home was very clean and had everything we needed. Beds were comfortable. Easy to find and close to everything. "
United States
Andrea S.
The price is ￥35,717
￥97,834 total
includes taxes & fees
May 18 - May 19
The Links! - Luxury Golf Retreat with Golf Simulator
Exterior

Edgewater Villa: 4 Bedroom, Sleeps 14!

Edgewater Villa: 4 Bedroom, Sleeps 14!
Sheboygan
8.6 out of 10, Excellent, (13 reviews)
"Nice property, close to the beach. It was perfect for our weekend getaway. "
United States
Rebecca B.
The price is ￥80,164
￥144,087 total
includes taxes & fees
May 18 - May 19
Edgewater Villa: 4 Bedroom, Sleeps 14!
Exterior

The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (59 reviews)
"Great spot, super close to town (and the always great Off The Rail cafe). Clean and quiet. Used as a base for track time at Road America."
United States
Scott G.
The price is ￥31,589
￥43,375 total
includes taxes & fees
May 19 - May 20
The Esker Ridge Chalet, Pristine Elkhart Solitude
Living area

The Historic Downtown Suite

The Historic Downtown Suite
Sheboygan Falls
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely wonderful experiencethis place is darling!!!! We will be staying here again"
United States
Kristin E.
The price is ￥19,049
￥34,029 total
includes taxes & fees
May 25 - May 26
The Historic Downtown Suite
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Waldo Hotel Reviews

The Osthoff Resort

The Osthoff Resort

10/10 Excellent
"Front desk staff was friendly and efficient; property is very clean and lovely; the hallways are forever long; the guest room was large with a fridge and micro AND a comfy balcony (screen door needs repair other than packing tape); dinner at the elk room was delightful & festive - lovely weekend."
Margaret 2-night trip
Posted 3 hours ago
The Osthoff Resort

Find out more about Waldo

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Look no further and take a look at our great range of rental properties in Waldo!

Frequently asked questions

Can I find vacation rentals in Waldo?

Yes, there are vacation rentals close to top attractions in Waldo, or you can go with a more secluded option if you're looking for relaxation.

What are some of the best vacation home rentals in Waldo?

Three bedroom ranch style pet friendly home with a patio & theatre room!: Visitors like this Waldo vacation home rental. It offers a patio, a pool table, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Waldo?

While exploring the area, visit family-friendly sights like Blue Harbor Resort & Conference Center Water Park, or get outside and enjoy nature at Kohler Park Dunes State Natural Area. In the larger area, you’ll find The Bull at Pinehurst Farms Golf Course and Road America.

What’s a vacation rental in Waldo like?

Vacation rentals are privately owned properties where you can stay for a long or short time in Waldo. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family getaway.