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.

Oct 19 – 26

G$22,610 GYD per night

Guest favorite

Cabin in Elkhart Lake

4.99 out of 5 average rating, 192 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.

Dec 3 – 10

G$42,741 GYD per night

Guest favorite

Castle in Cleveland

5.0 out of 5 average rating, 98 reviews

Castle Vineyard –HOT TUB, Theater, Golf Sim, Sauna

As seen on the cover of Haven, a luxury home magazine! This masterpiece was built over the course of seven years and is officially open to the public in 2022! For travelers who want an exclusive taste of Tuscany without the hassle of jetting across an ocean, "The Castle Vineyard" is the place to stay. The dramatic, spellbinding stone castle proudly overlooks over twenty acres of idyllic rolling hills and a gorgeous, working vineyard. Once inside, the interior does nothing to dispel the magic.

Feb 26 – Mar 5

G$195,838 GYD per night

Guest favorite

Townhouse in Sheboygan

4.97 out of 5 average rating, 117 reviews

Family Friendly Riverfront Escape|HUGE Game Room

Welcome to The WAVE – your ideal family friendly retreat nestled along the scenic Sheboygan River, just minutes from the beaches of Lake Michigan. As you step into The WAVE, you'll be greeted by a tastefully designed interior featuring LUX furnishings that exude both style and coziness. The accommodations include a King Suite with a riverfront balcony and a Guest Room with 2 queen beds. Entertainment is taken to a whole new level with our 500 sq ft game room with a 130-inch projection screen.

Nov 6 – 13

G$25,417 GYD 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).

Feb 18 – 25

G$44,138 GYD per night

Guest favorite

Cottage in Fond du Lac

4.97 out of 5 average rating, 235 reviews

Cozy Guest House with Lake views.

Our remodeled two bedroom Guest House is adjacent to our Cottage and offers beautiful lake views. Access to Lake Winnebago available at near by boat launches. Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen bed and 2 twin beds, 1 full bathroom, and a fully stocked newly remodeled kitchen. Perfect getaway for some R&R with family or friends.

Sep 13 – 20

G$14,080 GYD per night

Guest favorite

Home in Manitowoc

5.0 out of 5 average rating, 100 reviews

Rolling Hills Retreat~Hot Tub~KING Bed~Woods view

Reconnect with loved ones in a desirable neighborhood just outside town limits. Easy access to all of Manitowoc and surrounding communities. Minutes from I-43, offering easy commute to Whistling Straits, and Green Bay (20-30 mins away). Home offers both convenience and privacy. The layout provides a great opportunity for traveling coworkers to have their own space, with full bathrooms conveniently located next to each bedroom. Infant and toddler items available upon request.

Feb 6 – 13

G$78,367 GYD 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.

Nov 1 – 8

G$18,564 GYD 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

G$17,997 GYD 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

Oct 4 – 11

G$11,779 GYD 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!

Nov 2 – 9

G$21,951 GYD 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.

Mar 5 – 12

G$36,508 GYD 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

May 9 – 16

G$63,997 GYD 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

G$92,217 GYD per night

Guest favorite

Cabin in Newton

5.0 out of 5 average rating, 13 reviews

Modern Country Retreat

Sep 3 – 10

G$43,687 GYD per night

Guest favorite

Home in Reedsville

4.98 out of 5 average rating, 41 reviews

Newly remodeled farmhouse, quiet, comfy, and cozy.

Feb 27 – Mar 6

G$25,351 GYD 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

G$20,114 GYD per night

Guest favorite

Apartment in Manitowoc

4.91 out of 5 average rating, 76 reviews

Lower Apt steps from Downtown and the Lake!

Jul 15 – 22

G$19,458 GYD per night

Guest favorite

Cottage in Sheboygan

5.0 out of 5 average rating, 68 reviews

Cozy one bedroom cottage near lake Michigan!

Aug 10 – 17

G$28,468 GYD per night

Guest favorite

Apartment in Sheboygan

5.0 out of 5 average rating, 88 reviews

Modern Upstairs Apt - Steps from Lake Michigan

Mar 12 – 19

G$27,538 GYD 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
G$29,198 GYD 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

Cabin in Newton

Home in Reedsville

Home in Manitowoc

Apartment in Manitowoc

Cottage in Sheboygan

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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