Cleveland Holiday Rentals

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Holiday Rentals in Cleveland

Aparthotel in Elkhart Lake

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

2.5 star property
8.6 out of 10, Excellent, (1009)
"Would definitely stay here again!"
United States
Donna
The price is AU$215
includes taxes & fees
18 Dec - 19 Dec
Grandstay Residential Suites Hotel - Sheboygan

Villa in Elkhart Lake

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 AU$422
includes taxes & fees
5 Dec - 6 Dec
First Floor Pet Friendly Queen Suite with Single Pull-out

Villa in Elkhart Lake

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 AU$422
includes taxes & fees
5 Dec - 6 Dec
Modern Room Near Indoor Pool

Holiday Home in Sheboygan

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 AU$292
includes taxes & fees
9 Dec - 10 Dec
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Holiday Home in Oostburg

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 AU$244
includes taxes & fees
8 Dec - 9 Dec
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Apartment in Manitowoc

9.8 out of 10, Exceptional, (15)
"Very clean, and tastefully decorated…would rent again:)"
United States
Kim B.
The price is AU$346
includes taxes & fees
8 Dec - 9 Dec
2nd floor loft near the lake!

Holiday Home in Two Rivers

10.0 out of 10, Exceptional, (32)
"We came just to relax and have fun. We enjoyed sitting out on the patio with our dog and books and having a bonfire in the fire pit. The home is very well labeled and cozy—we loved it! "
United States
Jeremy E.
The price is AU$347
includes taxes & fees
16 Dec - 17 Dec
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

Apartment in Ellis Historical District

9.8 out of 10, Exceptional, (24)
"Top notch, close to everything you want in Sheboygan "
United States
Cody
The price is AU$201
includes taxes & fees
15 Dec - 16 Dec
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Cottage in Sheboygan

3.0 star property
The price is AU$610
includes taxes & fees
18 Dec - 19 Dec
Large Backyard, Walk to Hospital: Sheboygan Abode!

Apartment in 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 AU$284
includes taxes & fees
8 Dec - 9 Dec
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Apartment in 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 AU$272
includes taxes & fees
4 Jan - 5 Jan 2026
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

Villa in Elkhart Lake

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 AU$644
includes taxes & fees
10 Dec - 11 Dec
Upscale Waterfront and Pool View Condo!!

Apartment in Sheboygan

10.0 out of 10, Exceptional, (28)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
*NEW* Sleeps 8 & Spacious!

Holiday Home in Two Rivers

9.8 out of 10, Exceptional, (37)
"House worked well for what we needed. Will look to book again if in the area another time. "
United States
Jodi S.
The price is AU$642
includes taxes & fees
30 Dec - 31 Dec
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach

Holiday Home in Sheboygan

10.0 out of 10, Exceptional, (39)
"Very clean, cute, great communication, location & walkability! "
United States
Sandee M.
The price is AU$588
includes taxes & fees
10 Dec - 11 Dec
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

Apartment in Sheboygan

10.0 out of 10, Exceptional, (3)
"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 AU$285
includes taxes & fees
4 Jan - 5 Jan 2026
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

Apartment in Downtown Sheboygan

9.8 out of 10, Exceptional, (9)
"The flat is gorgeous and in a fantastic location. "
United States
Sarah G.
The price is AU$389
includes taxes & fees
4 Jan - 5 Jan 2026
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Holiday Home in Ellis Historical District

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 AU$236
includes taxes & fees
6 Dec - 7 Dec
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
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 favourite 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 depend 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 AU$216 per night. Entering your travel dates in the search wizard might find you 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.