Cleveland Holiday Rentals

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Our top choices for Cleveland holiday rentals

Aparthotel in Elkhart Lake

Victorian Inn Elkhart Lake Wisconsin
4.0 star property
8.8 out of 10, Excellent, (3)
"Perfect location, great amenities."
United States
Deirdre
Victorian Inn Elkhart Lake Wisconsin

Aparthotel in Downtown Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, (1013)
"Would definitely stay here again!"
United States
Donna
The price is NZ$243
includes taxes & fees
5 Jan - 6 Jan 2026
Grandstay Residential Suites Hotel - Sheboygan
10.0 out of 10, Exceptional, (2)
"So convenient to all things Elkhart Lake. Great accommodations and host. Would highly recommend!"
United States
Brenda H.
The price is NZ$516
includes taxes & fees
31 Dec - 1 Jan 2026
First Floor Pet Friendly Queen Suite with Single Pull-out
10.0 out of 10, Exceptional, (32)
"We had a relaxing stay in Two Rivers. This property is conveniently located to the beach and several restaurants. The house is perfect for families or anyone looking to take a break and relax. The host was great. We are definitely coming back."
United States
Angela S.
The price is NZ$406
includes taxes & fees
4 Jan - 5 Jan 2026
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
10.0 out of 10, Exceptional, (116)
"We loved the cozy cottage and cuddled up with books under the afghans on the cool evenings. The lake was a pleasant walk away."
United States
bev w.
The price is NZ$253
includes taxes & fees
5 Jan - 6 Jan 2026
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
10.0 out of 10, Exceptional, (4)
"Very clean and good location; nice place for our dog; we would definitely stay again if the opportunity presents itself."
United States
Stephanie K.
The price is NZ$292
includes taxes & fees
11 Jan - 12 Jan 2026
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

Villa in Elkhart Lake

Modern Room Near Indoor Pool
9.6 out of 10, Exceptional, (4)
"Our host was extremely responsive and resourceful. The room was very clean and nice. "
United Kingdom
Brandon B.
The price is NZ$495
includes taxes & fees
31 Dec - 1 Jan 2026
Modern Room Near Indoor Pool

Apartment in Sheboygan

Logan Ave Holiday House - Upper
9.4 out of 10, Exceptional, (3)
"We had a great stay here during the boat races. The host was so nice and left us local cheese & beer to welcome us to the house/city. We would definitely stay here again!"
United States
MELISSA C.
The price is NZ$505
includes taxes & fees
4 Jan - 5 Jan 2026
Logan Ave Holiday House - Upper
9.8 out of 10, Exceptional, (24)
"Great place! Nice location and very comfortable. "
United States
Jana F.
The price is NZ$224
includes taxes & fees
28 Dec - 29 Dec
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
9.2 out of 10, Wonderful, (10)
"Coastal Comfort was very clean, pleasantly decorated and comfortable. It is within driving distance to the lake as well as restaurants in Sheboygan. Perfect stay for the two of us. "
United States
Kim K.
The price is NZ$274
includes taxes & fees
5 Jan - 6 Jan 2026
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
10.0 out of 10, Exceptional, (1)
"In town for family celebration. This was a convenient location to my parent’s home! Thanks!"
United States
Shelly E.
The price is NZ$274
includes taxes & fees
6 Jan - 7 Jan 2026
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
9.8 out of 10, Exceptional, (9)
"The flat is gorgeous and in a fantastic location. "
United States
Sarah G.
The price is NZ$428
includes taxes & fees
11 Jan - 12 Jan 2026
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
10.0 out of 10, Exceptional, (6)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
United States
Stacy P.
The price is NZ$315
includes taxes & fees
13 Jan - 14 Jan 2026
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
3.0 star property
The price is NZ$689
includes taxes & fees
5 Jan - 6 Jan 2026
Large Backyard, Walk to Hospital: Sheboygan Abode!
10.0 out of 10, Exceptional, (39)
"Very clean, cute, great communication, location & walkability! "
United States
Sandee M.
The price is NZ$678
includes taxes & fees
13 Jan - 14 Jan 2026
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
9.8 out of 10, Exceptional, (255)
"Beautiful view and perfect for our Wisconsin lake getaway."
United States
Holly A.
The price is NZ$536
includes taxes & fees
31 Dec - 1 Jan 2026
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Apartment in Sheboygan

Sleeps 7{SPACIOUS}Pets Welcome!
9.4 out of 10, Exceptional, (3)
"Great location and amenities. Would definitely book again!"
United States
Elizabeth S.
The price is NZ$575
includes taxes & fees
13 Jan - 14 Jan 2026
Sleeps 7{SPACIOUS}Pets Welcome!
2.0 star property
9.6 out of 10, Exceptional, (12)
"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 NZ$262
includes taxes & fees
29 Dec - 30 Dec
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
10.0 out of 10, Exceptional, (4)
"We were in town for activities at Road America. The location of this villa is ideal and only a couple of miles from the track"
United States
Jason A.
The price is NZ$866
includes taxes & fees
27 Dec - 28 Dec
Upscale Waterfront and Pool View Condo!!

Apartment in Sheboygan

*NEW* Beautiful & Convenient!
9.8 out of 10, Exceptional, (19)
"The place was perfect for our family! Clean, 3 bedrooms, nicely furnished and equipped. The hosts were terrific. Provided all the info and were very responsive. 1st rate experience!"
United States
Todd S.
The price is NZ$573
includes taxes & fees
12 Jan - 13 Jan 2026
*NEW* Beautiful & Convenient!
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 Cleveland Hotel Reviews

Find out more about Cleveland

Everything you need to know about Cleveland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cleveland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cleveland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cleveland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cleveland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cleveland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cleveland holiday rentals we have selected for you start as low as NZ$243 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cleveland rentals

At Expedia, we put the best Cleveland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cleveland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cleveland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cleveland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Cleveland?

Yes, there are holiday rentals close to the most popular sights in Cleveland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cleveland has to offer?

Insane luxury beachfront estate - complete with indoor pool, arcade and theater!: This highly rated holiday home rental in Cleveland is located on a lake, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Cleveland?

Expedia has 9 holiday rentals for your stay in Cleveland.

What can I see and do in Cleveland?

Lake Michigan and Dairyland Park are a couple of lovely local spots to get outside and enjoy nature. While here, Veterans Memorial Park and Hika Bay are other places worth a visit.

What are holiday rentals like in Cleveland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cleveland. Holiday rentals feature amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.