Cleveland Holiday Rentals

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Our top choices for Cleveland holiday rentals

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, (26 reviews)
"Communicative host, good location, comfortable and clean apartment. "
United States
Hannah T.
The price is AU$186
includes taxes & fees
8 June - 9 June
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
3.0 star property
Two Rivers
The price is AU$572
includes taxes & fees
17 June - 18 June
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

Apartment Centrally Located

Apartment Centrally Located
Plymouth
The price is AU$274
includes taxes & fees
17 June - 18 June
Apartment Centrally Located

2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (18 reviews)
"The location was amazing and the place is really nice! Absolutely love that it is dog friendly and the host is really responsive! We will definitely be staying again! "
United States
Emily G.
The price is AU$133
includes taxes & fees
6 July - 7 July
2nd floor loft near the lake!

Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.6 out of 10, Exceptional, (5 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
Logan Ave Holiday House - Upper

Apartment near many locations.

Apartment near many locations.
Plymouth
9.0 out of 10, Wonderful, (2 reviews)
"This property is like where a grad school couple might live during the school year. The area is nice, safe, and quiet with nice open spaces outside and a pond with plentiful parking. It is the perfect location if going back and forth to Road America yet close enough for trips into Plymouth and Sheboygan."
United States
carl f.
The price is AU$306
includes taxes & fees
23 June - 24 June
Apartment near many locations.

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,041 reviews)
"Will remember to stay there again."
United States
Sonia
The price is AU$300
includes taxes & fees
21 June - 22 June
Grandstay Residential Suites Hotel - Sheboygan

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
10.0 out of 10, Exceptional, (15 reviews)
"We came for a girl's weekend and the house was perfect for us. The location is great (walking distance to town), the house was clean and we appreciated having the well stocked kitchen. I would definitely stay again!"
United States
Cinda Z.
The price is AU$426
includes taxes & fees
7 June - 8 June
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
Sheboygan
The price is AU$578
includes taxes & fees
16 June - 17 June
Large Backyard, Walk to Hospital: Sheboygan Abode!

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
Two Rivers
9.0 out of 10, Wonderful, (6 reviews)
"Great place to stay."
United States
Melissa B.
The price is AU$575
includes taxes & fees
16 June - 17 June
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Sheboygan
9.8 out of 10, Exceptional, (15 reviews)
"Welcoming and attentive hosts with helpful recommendations, clean and cozy space. "
United States
Brenda R.
The price is AU$490
includes taxes & fees
8 June - 9 June
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
Sheboygan
The price is AU$574
includes taxes & fees
8 June - 9 June
Large Backyard, Walk to Hospital: Sheboygan Abode!

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, (5 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$445
includes taxes & fees
11 June - 12 June
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

Brillion 2‑Bedroom Suite w/ Full Kitchen Near Ariens - Unit # 3

Brillion 2‑Bedroom Suite w/ Full Kitchen Near Ariens - Unit # 3
Brillion
10.0 out of 10, Exceptional, (1 review)
"Apartments were clean with easy access. Centrally located entertainment room was enjoyed by my granddaughter with claw machines, games, and TV. It is a newer property and still needs a few touches, like wall decor to soften the echoes. A bench outside the individual rentsls would be nice for seating, but there's a great area out back with chairs and heating if needed. "
United States
Debby
Brillion 2‑Bedroom Suite w/ Full Kitchen Near Ariens - Unit # 3

The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (59 reviews)
"Great spot, super close to town (and the always great Off The Rail cafe). Clean and quiet. Used as a base for track time at Road America."
United States
Scott G.
The price is AU$381
includes taxes & fees
17 June - 18 June
The Esker Ridge Chalet, Pristine Elkhart Solitude

Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Reedsville
9.8 out of 10, Exceptional, (33 reviews)
"Great place for family to stay for wedding of grandson. "
United States
Dawn C.
The price is AU$672
includes taxes & fees
8 June - 9 June
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

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, (174 reviews)
"Great place would go back"
United States
William
The price is AU$466
includes taxes & fees
18 June - 19 June
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

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, (41 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$589
includes taxes & fees
23 June - 24 June
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

The Beach town bungalow

The Beach town bungalow
Sheboygan
The price is AU$553
includes taxes & fees
5 July - 6 July
The Beach town bungalow

Newly Updated! Downtown & Shore

Newly Updated! Downtown & Shore
Sheboygan
9.8 out of 10, Exceptional, (6 reviews)
"Have stayed in all but one unit on this property and i must say, they are absolutely amazing!"
United States
Elizabeth S.
Newly Updated! Downtown & Shore
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$300 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 12 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.