Vacation rentals in Cleveland

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Top-rated vacation rentals in Cleveland

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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 29 – Jan 5

ﺩ.ﺇ398 per night

Guest favorite

Cottage in Oostburg

4.97 out of 5 average rating, 232 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.

Oct 25 – Nov 1

ﺩ.ﺇ641 per night

Guest favorite

Home in Cleveland

4.83 out of 5 average rating, 12 reviews

Private lake home near Whistling Straits Kohler

Walk to your private beach without a bluff! Lakeglass Cottage is situated on 5 beautiful acres with over 300 feet of private beach. Offering breathtaking views of Lake Michigan, easy water access, 2 acres of flat lawns, walking trails through woods and prairies, and ample parking. This luxuriously appointed mid century modern home has everything you need and is just feet away from the beach. Lakeglass Cottage is the perfect place for you to relax and make precious memories with your family.

Oct 15 – 22

ﺩ.ﺇ1,769 per night

Guest favorite

Home in Cleveland

4.95 out of 5 average rating, 131 reviews

Modern Home Just 5 Minutes from Whistling Straits

My home is just minutes from Whistling Straits Golf, Road America, Lake Michigan, Parks, Hiking, Biking, Snowshoeing, and Cross Country Skiing. You’ll love my place as it's newly remodeled, modern & cozy. The kitchen and living areas have high ceilings, sky lights & new furniture. The large outdoor living area is perfect for social time. My favorite is the heated bathroom floors. My place is perfect for golfers, wedding groups, couples, business travelers, and families (with kids & dogs).

Apr 14 – 21

ﺩ.ﺇ777 per night

Guest favorite

Home in Sheboygan

4.96 out of 5 average rating, 153 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.

Feb 27 – Mar 6

ﺩ.ﺇ497 per night

Guest favorite

Home in Sheboygan

4.97 out of 5 average rating, 151 reviews

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.

Jun 22 – 29

ﺩ.ﺇ566 per night

Guest favorite

Apartment in Sheboygan

4.92 out of 5 average rating, 398 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.

Apr 8 – 15

ﺩ.ﺇ302 per night

Guest favorite

Home in Glenbeulah

4.98 out of 5 average rating, 111 reviews

Stay at Sunrise LLC, Like being at Grandma's

Welcome to Stay at Sunrise LLC. We offer a clean and comfortable home for your vacation enjoyment. We are in a rural farm area, the recreation trail head is 3 miles east of us as well as the Wade House, we are near the Kettle Moraine State Forest and the Ice Age Trail and 7 miles from Road America. Large yard, Fire pit, picnic table, child swing set. Garage parking on site if arranged in advance. Smoking is allowed outside of the home. No pets allowed.

Mar 14 – 21

ﺩ.ﺇ317 per night

Guest favorite

Apartment in Sheboygan

4.84 out of 5 average rating, 183 reviews

Sheboygan Surf House "Jetties"

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our Urban living oasis is a fully equipped studio apartment conveniently located in the heart of downtown, just steps from bars and restaurants and only blocks to Lake Michigan South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake, Kite boarding, charter fishing, a Wedding or leisure time SSH is perfect for you. Support Dog friendly

Dec 18 – 25

ﺩ.ﺇ236 per night

Superhost

Guesthouse in Sheboygan

4.83 out of 5 average rating, 367 reviews

Carriage House Sheboygan, Lake Mich beach access!

The Carriage House is the perfect getaway. Located in a beautiful historic neighborhood with Lake Michigan public beach access across the street, 100 yards away. Ideal for a family of four or an individual in town for business. Amenities have been thoughtfully placed to create the most comfortable and convenient stay for guests. We pride ourselves on ensuring you enjoy your stay with us and guarantee you'll love the neighborhood!

Oct 16 – 23

ﺩ.ﺇ394 per night

Guest favorite

Apartment in Waldo

4.98 out of 5 average rating, 259 reviews

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.

Mar 21 – 28

ﺩ.ﺇ392 per night

Guest favorite

Condo in Sheboygan

4.99 out of 5 average rating, 103 reviews

Downtown Beachside Condo with Lake Michigan Views

You will see & hear the beauty of Lake Michigan during your stay at this main floor condo. A deck to the north allows views of the magnificent Blue Harbor Resort. The south deck gives more amazing views of the lake, plus a park just steps out the back door. You can stroll the beach, walk the River Boardwalk, or tour our historical downtown full of shops, art, & exquisite restaurants - walkable from the condo.

Jan 10 – 17

ﺩ.ﺇ651 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Cleveland vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Cleveland

Guest favorite

Home in Cleveland

4.97 out of 5 average rating, 36 reviews

Lake Michigan Views minutes to Whistling Straights

Jun 9 – 16

ﺩ.ﺇ1,269 per night

Guest favorite

Home in Newton

5.0 out of 5 average rating, 23 reviews

Lake Home with Sweeping Views of Lake Michigan.

May 8 – 15

ﺩ.ﺇ1,624 per night

Guest favorite

Apartment in Manitowoc

4.91 out of 5 average rating, 76 reviews

Lower Apt steps from Downtown and the Lake!

Sep 8 – 15

ﺩ.ﺇ249 per night

Guest favorite

Cabin in Newton

5.0 out of 5 average rating, 13 reviews

Modern Country Retreat

Mar 15 – 22

ﺩ.ﺇ769 per night

Guest favorite

Home in Reedsville

4.98 out of 5 average rating, 41 reviews

Newly remodeled farmhouse, quiet, comfy, and cozy.

Oct 3 – 10

ﺩ.ﺇ446 per night

Guest favorite

Townhouse in Sheboygan

4.94 out of 5 average rating, 81 reviews

Danz Sheboygan Retreat. Newly Remodeled in 2021.

Nov 11 – 18

ﺩ.ﺇ361 per night

Guest favorite

Home in Manitowoc

4.85 out of 5 average rating, 87 reviews

Brick Tudor Vacation House Close To Lake Michigan.

Dec 3 – 10

ﺩ.ﺇ354 per night

Guest favorite

Apartment in Sheboygan

5.0 out of 5 average rating, 88 reviews

Modern Upstairs Apt - Steps from Lake Michigan

Nov 7 – 14

ﺩ.ﺇ485 per night

Show all

Quick stats about vacation rentals in Cleveland

Total rentals
10 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
220 reviews
Nightly prices starting at
ﺩ.ﺇ514 before taxes and fees

Frequently Asked Questions

Do house rentals in Cleveland have wifi?
Absolutely! We offer over 10 house rentals with wifi in Cleveland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Cleveland have free parking?
Absolutely! We offer over 10 house rentals with free parking in Cleveland. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Cleveland?
Cleveland has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Cleveland?
Experience the best of Cleveland with our house rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Cleveland have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Cleveland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Cleveland have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Cleveland. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Cleveland

Top-rated vacation rentals in Cleveland

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Cleveland vacation rentals

Other great vacation rentals in Cleveland

Home in Cleveland

Home in Newton

Apartment in Manitowoc

Cabin in Newton

Home in Reedsville

Townhouse in Sheboygan

Home in Manitowoc

Apartment in Sheboygan

Quick stats about vacation rentals in Cleveland

Total rentals

Popular amenities

Wifi availability

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Cleveland have wifi?

Do house rentals in Cleveland have free parking?

Are there family-friendly vacation rentals in Cleveland?

How much does it cost to stay in house rentals in Cleveland?

Do house rentals in Cleveland have air conditioning?

Do house rentals in Cleveland have a kitchen?

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