Cleveland Holiday Rentals

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Our top choices for Cleveland holiday rentals

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,018 reviews)
"Great start!! Will be back!"
United States
Venir
The price is AU$212
includes taxes & fees
19 Jan - 20 Jan
Grandstay Residential Suites Hotel - Sheboygan

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Two Rivers
10.0 out of 10, Exceptional, (32 reviews)
"Adorable very clean cottage right on the river. Nice backyard with beautiful views and if you bring your furry friend, plenty of room for your doggie to roam and play out back. Close to beautiful Neshota Beach and lots of dining options. "
United States
Pamela S.
The price is AU$320
includes taxes & fees
19 Jan - 20 Jan
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Sheboygan
10.0 out of 10, Exceptional, (12 reviews)
"Great place to stay and even better hosts’. The house is conveniently located to everything we wanted to explore and was a great place to unwind after a long day. The host was very helpful and made sure we were settled in and having a good time. Would love to come back soon! "
United States
Riley W.
The price is AU$202
includes taxes & fees
19 Jan - 20 Jan
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
Sheboygan
9.8 out of 10, Exceptional, (12 reviews)
"It was an excellent place! Very comfortable, nice neighborhood, clean and exactly as described. We were very surprised and pleased with the welcome items left in the fridge! We Will definitely stay there again! "
United States
Kathy J.
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.8 out of 10, Exceptional, (24 reviews)
"Great place! Nice location and very comfortable. "
United States
Jana F.
The price is AU$198
includes taxes & fees
21 Jan - 22 Jan
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Sheboygan
10.0 out of 10, Exceptional, (6 reviews)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
United States
Stacy P.
The price is AU$270
includes taxes & fees
19 Jan - 20 Jan
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Downtown Sheboygan
9.8 out of 10, Exceptional, (9 reviews)
"The flat is gorgeous and in a fantastic location. "
United States
Sarah G.
The price is AU$358
includes taxes & fees
19 Jan - 20 Jan
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Sheboygan
10.0 out of 10, Exceptional, (4 reviews)
"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$258
includes taxes & fees
1 Feb - 2 Feb
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

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, (119 reviews)
"Lovely place and quiet"
United States
grandma d.
The price is AU$224
includes taxes & fees
19 Jan - 20 Jan
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (15 reviews)
"Very clean, and tastefully decorated…would rent again:)"
United States
Kim B.
The price is AU$339
includes taxes & fees
19 Jan - 20 Jan
2nd floor loft near the lake!

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"In town for family celebration. This was a convenient location to my parent’s home! Thanks!"
United States
Shelly E.
The price is AU$258
includes taxes & fees
15 Feb - 16 Feb
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Sheboygan
9.2 out of 10, Wonderful, (10 reviews)
"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$258
includes taxes & fees
11 Feb - 12 Feb
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
Sheboygan
The price is AU$613
includes taxes & fees
19 Jan - 20 Jan
Large Backyard, Walk to Hospital: Sheboygan Abode!

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
10.0 out of 10, Exceptional, (22 reviews)
"Wonderfully close to the lake. Sad there was no off street parking."
United States
Lucas T.
The price is AU$533
includes taxes & fees
19 Jan - 20 Jan
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Hot Tub, Fire Pit, Point Beach & Neshotah Beach

Hot Tub, Fire Pit, Point Beach & Neshotah Beach
2.0 star property
Two Rivers
The price is AU$637
includes taxes & fees
19 Jan - 20 Jan
Hot Tub, Fire Pit, Point Beach & Neshotah Beach

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.
2.0 star property
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 AU$232
includes taxes & fees
20 Jan - 21 Jan
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Sheboygan
10.0 out of 10, Exceptional, (40 reviews)
"We absolutely loved our stay. Everything was so well stocked and comfortable. Perfect location near the lake. Between the fenced in yard for the dog and the little play area for the kids, it couldn’t have worked out better."
United States
Jean S.
The price is AU$551
includes taxes & fees
19 Jan - 20 Jan
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

*NEW* Sleeps 8 & Spacious!

*NEW* Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (28 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
The price is AU$590
includes taxes & fees
17 Feb - 18 Feb
*NEW* Sleeps 8 & Spacious!

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, (173 reviews)
"Great place would go back"
United States
William
The price is AU$499
includes taxes & fees
25 Jan - 26 Jan
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

The Beach town bungalow

The Beach town bungalow
2.0 star property
Sheboygan
The price is AU$307
includes taxes & fees
17 Feb - 18 Feb
The Beach town bungalow
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$198 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?

Large Unique & Artistic Lake Michigan Beachfront House with Awesome Game Room: This holiday home rental outside of Cleveland is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a private garden and a selection of games.

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, Fischer Creek State Recreation Area and Veterans Memorial Park 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.